How Menswear Influencers Pack for Pitti Uomo (ft. Jack Collins)

When you buy something using the affiliate links on our site, we may earn a small commission.

In the winter of 2024, Raphael and Jack, one of our writers, attended Pitti Uomo in Florence, Italy. In this video, Jack will detail how he selected his outfits, what he brings when he travels, and how he packed for the trip, with input from Raphael.

Table of Contents
  1. Transcript:
  2. Conclusion

Their conversation has been lightly edited for clarity.

YouTube video

Transcript:

[Raphael] Welcome back to the Gentleman’s Gazette. Today, we are in Florence, and we packed for Pitti Uomo 105. So, Jack put together his outfits and he’s going to walk you through why he picked certain outfits, and we’ll have a great conversation. So, hi, Jack!

[Jack] Hey, Raphael! How’s it going?

[Raphael] Awesome! Well, you’re really good at packing, and you’re particularly good at putting it all up in a way so it looks like in a menswear haberdashery, but packing is not always easy. How do you approach it?

[Jack] Well, from my point of view, packing is all about getting the basic bits right—so underwear and socks are a guaranteed thing that you’re going to need to pack, but shirts are the first thing that I focus on.

[Raphael] Okay.

Jack focuses on shirts when packing and choses those colors that are easy to pair.
Jack focuses on shirts when packing and chooses those colors that are easy to pair.

[Jack] From the point of view that my shirt wardrobe, as you can see, is kind of mainly blues and whites—easy to wear and pair

[Raphael] Yeah, you have some blue here, mid blue, white pink, some like lighter blue with like a twill weave, kind of broad cloth, white evening shirt, and regular white shirt. So, the first thing you start with his shirts, right? But, if we go a step further, right, like for example: I came to Pitti Uomo in the third week of a three-week trip, so when I packed, I didn’t even know what the weather was going to be like. That means I had to be a bit more flexible, so how was it for you cause you came straight from England to Pitti, right?

[Jack] Correct! For me, that element came in here: the footwear was the first thing that I thought about when it comes to weather, and it’s kind of what I always think about whenever I’m packing for a trip. Especially in winter time cause in January, Florence can be cold and I feel the cold.

Jack always considers the weather when choosing what footwear to bring.
Jack always considers the weather when choosing what footwear to bring.

[Raphael] And by cold, you mean, you know, we had like 10° C, which is about 50° F. But, I always find like when you actually are out and about all day, it’s a lot colder than at home where you maybe just go to the grocery store walk, around a little bit, and go back home, right? Cause at Pitti Uomo, if you film… I mean, you’re out what? Six, seven hours a day?

[Jack] Easily, yeah, you’re doing a full day on your feet. You’ve got to be comfortable, and you’ve got to have an element of protection as well. But then, the challenge is making that stylish, so what I do is I start with boots.

[Raphael] Okay, and so, the trip you came on was like one week, correct? Or even a little more like 10 days?

[Jack] 10 days.

[Raphael] Okay, 10 days. Okay, so 10 day trip. So, you started with boots. Why boots?

The balmoral boots that Jack wears during the cold weather.
The balmoral boots that Jack wears during the cold weather.

[Jack] These boots, in particular, because they’re smart, they’re stylish, being a Balmoral.

[Raphael] Yeah, no. I like the look of them, for sure.

[Jack] But the color of these boots, they’re not brown, they’re not red; they’re somewhere in between

[Raphael] This antique cherry kind of, almost like a bit like museum calf, you know? I agree the color is great. So, it’s very versatile. You can easily combine it with other stuff. The two-tone makes it a different texture. That’s great.

[Jack] So, yeah, practical, stylish, and if you’ve got more than the one pair of shoes—which, for anything over two, three days, you really probably should have more than the one pair of shoes.

[Raphael] Oh, yeah, for sure.

These are the footwears that Jack has packed for Pitti Uomo
These are the footwear that Jack has packed for Pitti Uomo
Luxury Travel Shoe Horn Handmade

Fort Belvedere

Luxury Travel Shoe Horn Handmade

Antique Gold Ochre Silk Wool Pocket Square with Printed geometric medallions in beige, red and blue with cream contrast edge

Fort Belvedere

Antique Gold Ochre Silk Wool Pocket Square with Printed geometric medallions in beige, red and blue with Cream Contrast Edge

[Jack] Just to increase the longevity.

[Raphael] Oh yeah! And I also like the different styles. This is a Crockett & Jones. It says “Charlton.” Did you add toe taps to it?

[Jack] So, funny story: These are actually how I met one of my satorial friends, Linus. He sold me these, and he had got the toe taps installed beforehand. So, I inherited them pretty much as you see them. I have no issue with wearing used shoes.

Should you buy used shoes?

[Raphael] Oh, that’s true. But, I mean, these shoes you actually you had a blister, right? From these particular pair of boots?

[Jack] I did, yeah. And I’ll be be honest. That is all because of the toe cap. Right around here. They gave me a blister. And the realization with this one is the fact that I just haven’t done as long of a day as Pitti Uomo and Pitti is not a regular day for me.

[Raphael] You walk a lot. It’s a lot of steps, and that’s something to keep in mind, right? When you travel, you want shoes that are actually comfortable.

[Jack] This next pair is where comfort is really king.

[Raphael] So, travel shoe?

[Jack] 100% travel shoe, but also for those in between times so when you arrive and you’ve got some time to spare, and you want to maybe run to the grocery store and get some things for the AirBnB.

[Raphael] So, gray color? They’re like very like boat shoe-adjacent. They have a little heel but still kind of this rubber sole, leather kind of sock liner. So, interesting. These are your travel shoes, right? Cause I have a pair of gray boat shoes that look very similar. To me, it’s more of a summer shoe, but so this is like as comfortable as a sneaker? 

Jack's travel shoes
Jack’s travel shoes

[Jack] Yeah, exactly. Actually, more so for me because the sneakers that I’ve tried before, because they’re a flat sole… I’m just used to walking with a heel. So, this particular pair, because they’ve got that heel there and they’re a nice slim sole around the toe area, they feel similar to a dress shoe for me. But, they’ve got a really nice, slimmer sort of toe. So, they’re not as clunky as a boat shoe can be. But, yeah, these are absolutely my sneaker-adjacent shoes, which are just a touch smarter.

[Raphael] Cause similarly, I don’t go with particular travel shoes; I just try to take a pair that I would already bring and, if I’m kind of overweight or close overweight, I’ll wear the heaviest shoes when I travel. I also found that if you if you have a really well-fitting pair of bespoke shoes, because they fit so well when you’re on a long plane trip, your feet swell and you may have a hard time getting back in. So, like, “Oh, don’t take off your shoes!” Well, sometimes, it’s uncomfortable. So, keep that in mind if you’re in a long flight cause that can also be really painful if you may not have a shoehorn and you try to get back into your shoes. I’ve been there and done that.

Jack really likes these brown battered loafer when he travels as they are comfortable and soft.
Jack likes these brown battered loafers when he travels as they are comfortable and soft.

[Jack] Exactly. So, for me, when flying or traveling, it’s always something soft, always something that you can get in and out of easily without a shoehorn. So, I’ve got a pair of really battered loafers at home, which are perfect for travel because they’re super, super comfortable, soft, and I don’t care if I don’t need a shoe horn to get in and out.

[Raphael]: And with international travel, there are like TSA security regulations, regulations are different. Sometimes you have to take your shoes off, sometimes you don’t. So, yeah, having like your hiking boots with an extra strap and hooks and laces can be annoying. Okay, next pair?

[Jack] Next pair. So, this is my pair of evening shoes. They’re actually new to me. These ones are from Bowhill & Elliott in Norwich, which is actually where I live, and these are their new teal velvet with a flat bow, with what they call the “street slipper sole.” So, this is a hard rubber sole.

[Raphael] Looks like leather but it’s not. Exactly. So, it still looks smart but it’s a lot less slippy than leather and is designed to be worn out and about.

[Raphael] Now, this is really a special shoe, but you brought that because of a Black Tie event, right?

[Jack] Exactly! So it was a Black Tie event, but also the fact that it’s not a black Opera pump or anything that is absolutely “evening only” means that I could wear these during the day if I wanted to.

[Raphael] But, you did?

[Jack] I haven’t. Maybe. We’re not sure. But the wonderful thing about these is they’re light as, well, you probably notice because of their velvet. They are leather lined, but they’re super lightweight, and it’s a great way to add a little bit of flare.

[Raphael] Nice. Okay. Next pair.

Black loafers from George Cleverly
Black loafers from George Cleverly

[Jack] Is the pair that I’m wearing. These are a pair of black loafers from George Cleverly. Looking a little bit worse for wear. They’ve been doing a lot of walking today.

[Raphael] Oh, yeah. They’re like ready-to-wear. George Cleverly. Kind of elegant last. And I remarked on how often you wore these during a trip, right? Cause, sometimes, I’m like black loafers and loafer a bit more casual black, a bit more formal. But, you actually wore them a lot. You wore them with like your gray corduroy suit. You wore them with this like greenish cotton suit.

[Jack] Yeah, for me, it’s because they’re unlined. So, as you can see …they’re really comfortable. They flex easily and, unlike the boots, because there isn’t an element of toe cap, there’s nothing that’s interrupting the flex of my toes along the joints here.

[Raphael] You’re also less likely to get a blister.

Unlined black loafers from George Cleverly
Unlined black loafers from George Cleverly

[Jack] Exactly, yeah. I’m very lucky because I know that you have issues with fitting loafers comfortably.

[Raphael] My problem is the heel, and I talked to some other people, too. Like, you know, said like either it’s tight in the front and then it’s good in the back, or it’s loose in the front or, it’s good in the front and then too loose in the back. Other people seem to have that issue, too, with loafers, and loafers are hard to fit. Bespoke shoemakers say that ready-to-wear it’s just what it is. So, if you find a loafer that fits you well, consider yourself lucky.

[Jack] Buy it! The way that I get around that is, at home, these are on shoe trees which have the the handle style. So, what it does is: It’s just gently enforcing the thinness in the heel when the shoes are resting, so that when I wear them—because I have thin heels, too— they then are comfortable for me. So, I start with casual shirts first, and I lay those at the bottom of my case because I don’t mind. They’re casual. They’re going to be creased, and they’re, therefore, the easiest for me to re-iron when I get to the destination.

Shoe trees with handles
Shoe trees with handles

[Raphael] So, are you building the outfit around the shirt or you like, “I just have basic colors. I can wear them with everything.” That’s just what I naturally take next.

[Jack] Yeah, exactly. Second option. For me, it’s a case of: So, I’m wearing one today, which is just exactly the same as this—a white OCBD.

The Oxford Cloth Button Down Shirt

[Raphael] So, this is like a Drake’s?

[Jack] Yeah, then this one is from LA Shirts. Yeah, so in Naples. Really lovely. Kind of chicken foot buttons, mother of pearl. It’s nice, handmade buttonholes here.

[Jack] And if you can see, it’s super faded, so it’s light on the top of the sleeve, darker in there, which is nice because it’s a denim shirt that’s not super obvious. It’s not like a Levi’s denim shirt, where it’s very Western. This is definitely a sartorial denim shirt. So, yeah, these ones, because they’re really easy to pack and re-iron, and sometimes I might not even re-iron them. Sometimes, it’s a case of they’re easy to wear.

[Raphael] I like to bring shirts that don’t wrinkle a lot or are easy to wear; maybe even like steam things out just hang them in the shower, because you don’t always have an iron when you travel, and you may not always have a time so it’s best to have shirts that are kind of look great even out of the suitcase. Yeah, agreed.

[Jack] So, moving on to more formal shirts, we’ve got uh an experimental piece for me. I haven’t worn pink shirts before, but this is my first, and I actually really like it. This is from Edward Sexton.

Jacks Edward Sexton pink shirt
Jack’s Edward Sexton pink shirt

[Raphael] Edward Sexton has its kind of pinhole option. It’s interesting because, you know, they have this like. I have some, too, where they kind of made a whole punched a hole and then did a button hole here. They kind of sewed the round hole first and then made a smaller punch. Uh, yeah, probably if you have like an end right you’re not going to see it and it’s not going to move around. There’s no play but, um, has this kind of really cool collar, long more classic, which is really nice.

[Jack] The issue that I find with a lot of spearpoint collar that are available on the market nowadays is that they reenactment or vintage reproduction. And … I don’t want that super 1930s aesthetic, but I do want something that can take a collar bar or a collar pin.

[Raphael] Nice.

[Jack] So, that was the reason behind bringing this shirt. Pitti Uomo is exactly the place where you can try these things out.

[Raphael] And even you know if you don’t go to  Pitto Uomo, right? Like what was there hesitation of wearing pink shirts and why did you then decide to give it a try?

[Jack] My complexion. Um, basically working out whether pink would suit me, but seeing that this style was ticking a lot of boxes for me, and it had the color that I wanted, and it was on offer, helped kind of make that decision for me. So, I decided to go for it, and so far I like it.

[Raphael] Yeah, and I mean if you sometimes feel like you know there’s something you can’t wear, maybe it’s a bow tie, maybe it’s a certain color; it’s a bit like anxiety right when you’re anxious of something the solution is not to just never do it. It’s to maybe start with baby steps towards it so you can overcome that fear, and then over time, you feel more comfortable or maybe you decide really it’s not for me. But at least you tried and you know that that’s the case. Cool. Okay, so next then, you’ve got another kind of blue shirt, right? Kind of twill.

Two identical classic shirts in white and blue.
Two identical classic shirts in white and blue.


[Jack] So, this one and the one at front here, uh pretty much identical copies. These are from Proper Cloth, and this one is because I messed up my measurements on this one. If you can see, this one’s actually quite short. Quite short.

[Jack] But I wear high-waisted trousers, so it’s okay.

[Raphael] Not that big of a deal,  but you can see this is quite a bit longer here; few inches. Okay, all right.

[Jack] So, pretty much nothing to write home about with those but absolutely guaranteed to be versatile and work in any situation.

[Raphael] Nice, and then here, you got… That’s a cool one. T.M. Lewin, kind of detachable collar shirt.

[Jack] Exactly, so I brought two collars with me. One is a rounded collar, the other is a pointed collar. Haven’t decided which one I want to wear yet, but it’s a true Winchester style, and again, those colors allow me to wear collar jewelry.

Detachable collars to switch up a shirt's style.
Detachable collars to switch up a shirt’s style.

[Raphael] And they look different. I mean, if you are all about looks of the collar, detachable collars is a little stiffer. It’s just one of a kind.

[Jack] Exactly. The tie is held in a different way. It’s a little bit more difficult to put on when you’re used to soft, turn-down collars. Yeah, but like you say, it’s definitely a unique look.

[Raphael] Well, and you know, when you go to an event like Pitti, the two schools of thought: You could either say, “Hey, I create very specific outfits, and I only bring those clothes so then I wear exactly that,” but the problem is, well, what if someone, you know, throws some food on your wine or maybe you do it yourself or something happens, right? You need options and you need variety, and then, very few people have like you know three of each shirt. So, you just have to bring a few different things; and sometimes, it’s also the mood, maybe the weather changes, maybe you’re in a time crunch. All these things, right? If you’re in a hurry, you’re not going to put on your detachable collar shirt, you just scrap the one with the attached collar because it’s easier and quicker. Cool.

[Jack] And then, finally, we come to my evening shirt. This is from Emma Willis.

[Raphael] Bib. Getting a little wider. Sometimes I had one from Brooks Brothers that were like White Tie shirts that had a little opening here. So, it would help in adding your studs cause this is a shirt for studs, right? There are no button holes there. The collar, as well as the cuffs, and the French cuffs, are also in the same pique. So, what someone sees is all pique basically.

[Jack] Exactly. The cotton, as you can feel, is really nice, lightweight cotton on the sleeves and body.

[Raphael] What I like here is, you know, they put a layer of broadcloth behind it because when you have this Marcela pique, especially if it’s starched, right, you may experience some like nipple chafing, and you may Band-Aids to put them on; whereas with this, do you wear Band-Aids?

[Jack] No, and we can let you in on a secret that is absolutely a joke in the office—that nipple chafing is real. But yeah, otherwise, the details in this shirt, the color’s quite conservative, quite classic. Easy to wear with any Black Tie accessories and that’s what I like about this. It’s simple, it’s easy, it’s elegant.

[Raphael] Good. So, now, on to the jackets.

[Jack] Well, since we’ve been talking about Black Tie, let’s start with perhaps the loudest jacket in the bunch. This is my Black Tie jacket or, at least, it’s the jacket that I wore for a masquerade ball.

[Raphael] Not what like most people would have assumed you wore for Black Tie.

[Jack] And it’s worked for Black Tie as well.

A loud and unexpected Black Tie jacket
A loud and unexpected Black Tie jacket.

[Raphael] This is like, you know, Advanced Black Tie. I mean, it’s obviously… It’s silk—you have these silky knobs. It has elements of brown, black, and white, right? So, for something like Pitti, where it’s like about being different and being like trendsetting, that perfectly fits the bill. The lapels are beautiful, has kind of a bit of a belly here. You know, that the peak points up a little bit. I mean, it’s a 70s jacket, so they have these kind of somewhat larger buttons that are rounded.

[Jack] And this is one of my favorite features actually.

[Raphael] (reading label) “Stile Young Club, Confezioni San Remo

[Jack] I’m going to pretend that I understand what that means. But yeah, it’s one one of my favorite details is the double button on the cuff. I think it’s really nice. It’s unusual but it’s not so different that it’s crazy. The jacket’s crazy enough that I don’t need all of the other details to be crazy. But, although it’s not conventionally Black Tie, as soon as you put it with the Black Tie trousers and a simple shirt, it works very nicely.

[Raphael] It works. And even like if you wanted like four buttons here—there are no buttonholes—you could just you know take these buttons off on the other one, take these off and put the buttons of your choice on. I could see some mother of pearl buttons, like darker ones could be cool, right? If you wanted that look. No problem. You just have to replace all of them. Yeah, so you wore this jacket with the blue velvet loafers for the Black Tie, with the cummerbund studs, cufflinks. There’s no buttonhole here, so there is no boutonniere.

The True Meanings of Flowers, Revealed!

[Jack] No boutonniere. However…

[Raphael] I mean, you could add in one in after the fact but it’s always a little more tricky cause you need someone who can sew a buttonhole. Not all alterations tailors can do that. So I can see… Yeah, okay. Next up, we’ve got?

[Jack] Next up, I think we’ll go for this one. This is the most formal thing that I’ve brought other than the Black Tie ensemble. It’s a three-piece suit from Benson & Clegg. I got this one in a sample sale they did a few years back, and it needed a little bit of work done to it, but it was well worth it. I use the trousers on this suit so often. It’s a charcoal herringbone. You can see that there’s no detail on the waistband whatsoever; it’s just a plain waistband, single pleat. Really classic and easy to wear.

[Raphael] Yeah, ready-to-wear piece. Nice. So, here we have your latest addition, right?

[Jack] Indeed, this is a very special piece for me. 2023 was the year I decided I was going to go bespoke. Yeah, and this is a bespoke piece from The Anthology. They’re a tailor house based in Hong Kong, and they have trunk shows in London and other places in the world. So, it made it really easy for me to be able to speak to them and have this piece made.

[Raphael] It’s not your typical, you know… Most people are like, you know, “First bespoke suit, go conservative.” You know, navy suit, charcoal suit. You went with this corduroy. It’s like a gray corduroy, but it has a bit of a warm green tone to it.

Bespoke Tailoring Basics

[Jack] Which is really unusual. I think that’s why I went with it for my first piece, made bespoke, because it’s strangely versatile. The trousers can be worn with a sweater, which is why I decided to go for belt loops. It’s got suspender buttons in there as well, but the belt loops just add that level of versatility for me; and the jacket can be worn with denim, it can be worn with chinos.

[Raphael] I mean, you’re a person who really thinks long and hard about buying something. So, this wasn’t like an impulse buy on a whim. You thought about it long and hard. I mean, you like green. I mean, here’s another green suit that you’re wearing. What is that one?

[Jack] This one is from Natalino. It’s a very unusual piece because, like you say, it’s a green cotton; it’s a brushed cotton. So it’s got this really fun sort of texture to it. It can be buttoned in the standard sort of…

Green fabric of the suit
The green fabric of the suit

[Raphael] Two, kind of. But, then, you probably also want to put the inside so it works. Yeah. So the lapel shapes don’t become like uneven.

[Jack] But I much prefer it more like this. It’s very comfortable, very comfortable. Patch pockets makes it that little bit more casual, and this is actually the jacket that I traveled in. I stowed the trousers but traveled in the jacket.

[Raphael] It’s always a great tip when you kind of are, you know, close to your maximum luggage: wear the heavy things, wear the overcoat, wear the heavy shoes, the heavy whatever that can save you like 2 or 3 kilos—you know, 5 or 6 lbs—depending on what you got there.

[Jack] Exactly, and for me, this is a bag. You wear this, it’s got pockets in it—patch pockets. Doesn’t matter if you’ve got a few extra bits and pieces, it doesn’t spoil the line as much.

[Raphael] Nice. So we got here?

[Jack] Next up is trousers. Now these are moleskin. So, again, a brushed cotton. They’re quite plush. They’ve got a really nice hand to them.

[Raphael] And where were they from?

[Jack] These are from the Kingsman Collection. So I’m a big fan of the Kingsman series, and Mr. Porter did a collaboration with them. These aren’t ones that are featured in the film, but they’re easy to wear for me.

“Oxfords, Not Brogues?” Men’s Style Review of “Kingsman: The Secret Service”

[Raphael] You just like them. So, these are your kind of tuxedo pants here?

[Jack] These are Tom Ford tuxedo trousers. Oh, nice. T.J. Maxx, one of those rare gems that happens. But yeah, nice and classic.

[Raphael] So, yeah, it goes with your dinner jacket, right?

[Jack] Then, on the other end of the spectrum, white denim. Not only white denim, but white denim that perhaps a lot of you guys wouldn’t expect from a Gentleman’s Gazette person. But, these are from H&M. I got them in the sale.

[Raphael] It’s full spectrum, right? It’s like, it doesn’t mean that everything has to bespoke, right? So, we got bespoke to H&M, right? It’s like a, yeah, spectrum.

[Jack] And what’s surprising about these is the cut is actually quite classic. They’re not wide, but they’re also not skinny; and because they only cost me £10 probably—what 12 bucks—it means that I wear these to travel and I don’t mind if something bad happens to them because you can just stick them in the washing machine, blast them clean, and it’s easy.

[Raphael] Nice. So, here we got one more piece.

[Jack] This is a vintage waistcoat. So I’ve got a lot of use out of this to the point where this is probably the only waistcoat, other than from a three-piece, that I wear. The only thing I’d change about it is the lapels. They’re kind of 60s.

Jack brought his trusty brown waistcoat
Jack brought his trusty brown waistcoat.

[Raphael] Yeah, they’re very slim, but the buttons are kind of cool, you know. They look more like removable waistcoat buttons. This kind of weave in here. So, yeah, earthy tone, you know, works with a bunch of different jackets.

[Jack] Yeah, for a bit of extra warmth, you can put that under pretty much any of these, and it’s actually a nice piece to change out the waistcoat here for.

Why Did Men Stop Wearing Waistcoats (Vests)?

[Raphael] Especially when you don’t know what the wear is going to be like, having like… It could be like, you know, sweater vest, regular vest. Just layers that you can take on and off for friend. And then, we got here your overcoat. Did you travel with it?

[Jack] Yes, so I wore this to travel in. It’s heavy, therefore, I didn’t want to pack it, and I’ve only brought one overcoat with me—this and that.

[Raphael] Makes sense. If you’re on a… If you have to kind of pack lightly or you just have one suitcase, that’s the way to go. One overcoat, you travel with it. Perfect! And this is beautiful because it has these like, you know, light blue, green, kind of rust orange, light brown, kind of more darker brown. It has so many colors. It’s so easy to combine.

[Jack] Exactly, that’s why I brought it, cause it’s warm. It does the job. It’s quite a classic cut. It’s not thin.

[Raphael] It’s raglan. It has these like leather football buttons, and I mean, look at the armhole, right? It’s huge for a guy like you, but it also means you very easily get in and out with a jacket underneath of it. And you’re not waving for cabs or anything. So, that’s it. So, what’s this here? Hepworths. 100% virgin wool made in Northern Ireland, yeah.

[Jack] Yeah, it’s a lovely piece, and unlike many raglan coats that are around today, it hasn’t got the shirt collar. It’s got an actual collar and lapel, which adds that level of sartorial detail, which is just so much nicer for me. I always wear my collar flipped up on a coat, so being able to wear it like this, it’s a nice low gorge. It’s perfect for me.

Jack wears his overcoat with the collar up
Jack wears his overcoat with the collar up.

[Raphael] Yeah, and I mean, you wore it every day because you run cold anyways so I, on the other hand, I run hot. So that’s also something to understand: if you run hot or cold, know what you need. But, even I bring different stuff. Cool! So, then, let’s move on to accessories. You want to start over here?

[Jack] Sure, an essential for travel is a good bag. This is from Frank Clegg. I bought it pre-used, which meant that it was a lot cheaper, and although it doesn’t have a zip, I found that attaching this shoulder strap, which I’ve taken from a different bag, helps keep the bag closed when it’s worn over the shoulder or just simply like this.

[Raphael] And it has come in quite handy we like to the flea market you can put a camera in there, a gimbal, all sorts of stuff you unexpectedly buy when you’re in a different city. So, yeah, we did a video about, is the tote bag, you know? A fad or here to stay? So, if you want to learn more about that, check that out, okay? And then, you got a little hat there. Yep, this is an “in case” hat. I keep trying to get into fedoras and more classic hats, but this is perfect.

Are Tote Bags for Men Timeless, or Just a Trend?

[Raphael] Your warmer has their place, right? Nice Shetland wool.

[Jack] Again, very similar to the coat, lots of different colors in there, makes it easy to pair, but it’s also perfect to travel with. Look at that. It just folds down easy. Another travel essential for me—I come from England—umbrellas are my life.

[Raphael] See, in Minneapolis, like I think we have like rain, maybe like three days a year. So, an umbrella is not something that’s top of mine for me. I didn’t bring one this time. My wife, Teresa, she hates being wet, so she brings one. But, it’s not it’s a good idea. I mean, you can buy these cheap umbrellas when you need them in tourist cities, but this is, of course, much nicer.

As someone from England, an umbrella is among Jack's essentials.
As someone from England, an umbrella is among Jack’s essentials.

[Jack] A lot nicer, and we’re here for sartorial reasons.

[Raphael] Yeah, makes sense.

[Jack] It fits the bill. Plus, it fits in the bag beautifully.

[Raphael] Nice, okay. What else you got here?

[Jack] Here, I always like an element of knitwear when I’m traveling in winter. Turtlenecks, I found, are the easiest thing from the point of view that they replace a shirt on Sunday.

[Raphael] Totally, and that. But then, you don’t wear like no tie, necktie, ascot, no neckwear. But, it’s kind of a warmy feeling. I often times stay away from them because I feel I get too hot, especially in Europe. Often times things are warmer here in Italy than they would be in the US. So, I’m like, I don’t want something that I can’t take off, right? Like if you have a tie, you can take out the tie; and kind of, you have a vest, you can take out the vest. This is hard to take off because it’s an all or nothing kind of thing.

Turtlenecks are great with or without a jacket.
Turtlenecks are great with or without a jacket.

[Jack] And that’s where obviously we’re very different people. In that respect, I love the fact that I can take a jacket off and still feel dressed. Yeah, and for me, these are great things to dress in without having to think about it. Put an undershirt on, put the turtleneck on, you’re half dressed [Rahael] And packing is not a cooking recipe that, you know, it fits the bill for everyone, right? It’s like understand who you are. Do you run hot? Do you run cold? And then pack accordingly.

[Jack] When it comes to ties, for this trip, I wanted to bring ties that would work with everything because I’ve already got my shirts, suits, and shoes packed, so choosing ties was kind of easy. They had to work with predominantly gray-green tones because I knew I wasn’t likely to wear anything other than a bow tie with this.

[Raphael] So, when you pack like this, do you put stuff on your bed? On your wardrobe? So, you have it all next to each other, so you can visually see what goes together.

How To Pack A Suitcase For A Business Trip

[Jack] I’ll rearrange my wardrobe so that I bring the things that I want to take all into one space in the wardrobe, and then I kind of ignore the rest of the wardrobe. So, for ties, I’ve gone for two that have the these earthy tones—both of these are vintage.

Jack's Ties
Jack’s Ties

[Raphael] Kind of brown and gold with a J for Jack.

[Jack] Exactly! This was a perfect find. It’s polyester, but it just appealed to me.

[Raphael] Okay, and then, here you got more of a kind of bluish-grayish with a brown kind of wool tie.

[Jack] This is nice. This is actually made from a suiting wool. My second tailor had these ties in their shop, and I commented that I really liked this one and had to have it, and they gave it to me which was a pretty wonderful gesture.

[Raphael] And then this is more like madder silk-style tie. This even is one of ours, right, yeah? Fort Belvedere? Then, like, a knit tie with a different knit pattern, a pointed tip.

[Jack] As you can see, there’s been one or two more elements of black in here. More so than perhaps I used to wear. But, the black turtleneck, the black tie, black shoes— they’re just little flashes of black rather than doing that black monochromatic look.

A madder silk tie in Jack's Pitti Uomo wardrobe.
A madder silk tie in Jack’s Pitti Uomo wardrobe.
Madder Silk Tie in Bottle Green Macclesfield Neats Blue Orange Pattern - Fort Belvedere

Fort Belvedere

Madder Silk Tie in Bottle Green Macclesfield Neats Blue Orange Pattern



[Raphael] Well, if you have something like this, like that green or like the gray, it kind of tones it down.

[Jack] Yeah, 100%. For evening wear, I have my cummerbund and matching single-ended bow tie—both from Fort Belvedere. They’re great. I just love them. They’re in the moire silk style.

[Raphael] Yeah, don’t say anything wrong; otherwise, you might get fired. No, I’m just kidding. And I can see here, like, you basically, what you did is you used a little clip because it’s too… This is, I think, the bigger version. We may have… Okay, cause we don’t have this cummerbund in the small version, so you kind of makeshift cause you’re what—waist 32, 30?

[Jack] About a 30, 32.

[Raphael] Okay, so you kind of made that so it would work.

[Jack] But, this is fine because, when I’m wearing Black Tie, I’m not taking the jacket off. Only I know—well, you know as well now—that those pins are there. Yeah, so this one is from La Bowtique bow ties. Mickael is in London, and I wanted to support local. He’s decided to move purely into the realm of Black Tie, so…

[Raphael] And is this pre-tied?

[Jack] It’s pre-tied, but it is free tie. So you can untie it and retie it. It’s got a hook and eye clasp, which is what I wanted to go for, this bow—to understand more about how that can be interchangeable and kind of say the knot that you like the look of. So, I’ve been getting into silk scarves quite a bit recently. These, I originally thought would be more, like, for females because that’s traditionally what they have been. But, seeing them in colors and styles that are closely related to classic menswear, and indeed, the fact that this one’s just quite simple because it just uses the gold, the black, and a touch of white.

Silk Scarf in Black, Gold, and White
Silk Scarf in Black, Gold, and White

[Raphael] Allows you to do stuff, and that’s cool. That’s the thing about style, right? It evolves. You try something, and you’re like, “Maybe, oh, I don’t know if it can wear that,” and then maybe you see someone else doing it and you’re like, “Oh, maybe I could do that,” and you try it and then you like it and you get more or you don’t and… There’s no right or wrong way. There’s just something that, yeah, makes you feel comfortable, and if you’re into this and you enjoy this just like Jack and us, you know, you always want to kind of push the envelope a little bit. Nice. Okay, then, you got some suspenders here.

[Jack] Yep. Uh, so these are the only pair that I brought with me, so both of my full suits have suspender buttons, apart from this one, but uh, these…

[Raphael] What are those? Some vintage, too?

[Jack] These aren’t vintage, actually, no. These are because I’m a James Bond fan. Uh, if you’re a James Bond fan, you’ll recognize these from No Time To Die. Daniel Craig wears these in the opening scenes, and they have this really cool sort of crocodile texture. Uh, it’s mock croc.


[Raphael] It’s mock croc, yeah for sure.

[Jack] But the color is actually really versatile, this sort of blue-gray.

[Raphael] Blue-gray, yeah. Picks up a lot. Nice. and then you got like three pocket squares.

[Jack] So, the pocket squares. Uh, aside from the one that I’m wearing, which is an easy sort of… it’s cream, it’s not white but I like it. I’ve decided for three Fort Belvedere squares. This one you’re probably familiar with. It’s got our classic X-stitch, and it’s that really nice textured linen.

[Raphael] The handcrafted linen, it’s very open; it’s kind of very texture-y, right? It’s, it’s different than typical linen cause it has this two-tone, blue and white. And then you have some silk-wool pocket squares.

[Jack] Yeah.

[Raphael] And like the burgundy one. This one is super versatile. Like if I travel and I bring this, I know I can wear it with a lot.

[Jack] Well, exactly. That’s why I’ve brought these: when you get a pocket square that has a border and details on the inside,

[Raphael] So you can wear like just the border, you can wear just that, you can combine it. You get like more in one, which is really travel friendly. Yeah, great, great. And then uh travel shoehorn? Yeah that comes in really handy I have mine, too in the bag, right? It’s like wherever you go, where it’s you know TSA, you try something on–just having it available or with you is such an easy thing.

[Jack] As a fun fact, this never leaves the tote bag, it goes with me everywhere.

[Raphael] Same for me, and just say leave it in a travel bag. Makes sense. Awesome! Great! Um, let’s look at some other accessories here that you brought, and uh, we’ll switch over to the table. What’ve you got here?

[Jack] So, there’s a range of different things. So, some of these things are kind of everyday travel for me, and a few things are travel-specific. Of course, wash bag and a few bits and pieces that are already in the bathroom.

Everyday Carry – EDC Essentials for the Discerning Gentleman

[Raphael] Kind of looks like more little PU grain leather more like the leather I think from Louis Vuitton right.

[Jack] so this is actually a women’s makeup bag but it works perfectly for me.

[Raphael] For your size and what you travel with.

[Jack] A can of antiperspirant fits along the bottom just perfectly, and then shaving kit and things, and then this one goes in in my carry-on. Sorry, my checked luggage and then uh carry-on gets the smaller bag. So, it’s got things like my hair wax and some spare toothpaste; bits and pieces, but the rest of my things, uh, other than my hairspray. And aha!

[Raphael] Fortnum & Mason Breakfast Blend!

Jack packs tea when he travels.
Jack packs tea when he travels.

[Jack] Yes, as an Englishman through and through, uh, if you just uh, I need tea in my life. So, I always carry a couple of bags of tea in this little tin. You never know when you’re going to need some sustenance.

[Raphael] Nice. What’d you got here

[Jack] Uh so, that is a glasses case although I wear my glasses pretty much 24/7 apart from when I’m asleep, it’s a useful case to carry little bits and pieces. So, things like cufflinks, studs, collar jewelry, that’s where that lives.

[Raphael] Nice. Then you got the Got2Be Glued Blasting Freeze Spray.

[Jack] Yep, uh, so I use a combination of hair wax and hairspray.

[Raphael] This looks cool. Penhaligon’s.

Sample sizes are great for travelling.
Sample sizes are great for traveling.

[Jack] Yep, one of my favorite uh English brands for perfume. It’s a travel atomizer. So, you can get this one, I think it’s… I don’t know the exact amount, but you can get a really good amount of fragrance in there. If you’re spraying liberally, it won’t last you very long, but if you’re using something like…

[Raphael] For travel.

[Jack] Yeah. Something like the Roberto Ugolini collection, which has got a higher concentration of essential oils, you don’t need to spray very much, so.

Roberto Ugolini Fragrances

[Raphael] Well, plus I mean the Ugolini ones you brought those because we’re in Florence. Roberto Ugolini is from Florence. We’re going to take some photos and video from the bottles while we’re here cause it makes sense. Normally, like I travel with sample sizes um because I don’t want all the weight of the flacon, and it’s just too heavy. And yeah. So, this is not what you travel with regularly?

[Jack] No. I will travel with one fullsize fragrance, and then I’ll typically do a fragrance like an evening fragrance. Something that’s a little less versatile will be in the smaller atomizer, and then I’ll take an everyday fragrance in the full size.

[Raphael] Nice. All right, then. I see some gloves here. You got like a the dark green like lamb nappa.

[Jack] The gray peccary, as you are aware, these have been worn pretty much all the time I’ve been here. they’re cashmere-lined. So, they keep me warm. The gray color is excellent with all of the clothes that I’m wearing, and um I think are these the hydro peccary?

The gloves that Jack packed.
The gloves that Jack packed for winter in Florence.

[Raphael] I think so, yeah. Like we had them treated so they’re not like… the water kind of pearls off. Um, it’s kind of the same treatment you get for like, you know, ski jackets. It’s like this like durable water repellent exactly. Um, and then, I think they don’t longer do this treatment because there’s other kinds of treatments, but they can’t do this original treatment because of like the waste water usage in the environment, which is good, you know. I don’t want to uh have issues there. And this is like… these are made in Hungary, right? These are made in Hungary. This our current line. These were our older line also peccary but we made those in Peru. The current ones we have our superior leather, superior color, and everything, but you know you still have the old ones. They last, why change?

[Jack] Exactly, I’m not going to throw something out just because it’s not new.

[Raphael] No, absolutely not. These are me to last. And no matter what we do, you know, now or in 10 years, you can still wear those.

[Jack] Exactly. So, moving on from the gloves, uh I always carry two pens with me: a fountain pen for my own personal use and a ballpoint for signing receipts or checks something that needs kind of the ink to be dry pretty much instantly.

The Fountain Pen Guide

[Raphael] The 146 LeGrand!

[Jack] Exactly. That was a secondhand pen, but it’s beautiful condition. This is a Parker IM with a black fine nib refill, like I say, this is for when I need to quickly jot something down or if someone else needs a pen, it means that I can still do the gentlemanly thing and hand a pen but I’m not then getting my fountain pen rewritten in by someone that doesn’t appreciate how to use a fountain pen.

[Raphael] Nice. I see an empty passport here. So, it’s great that we’re working on some passport holders, so soon they’ll be available, and then, uh, Jack will have one, too.

Jack's accessories--his passport has no holder yet!
Jack’s accessories–his passport has no holder yet!



[Jack] Exactly! Looking forward to it! What is new, though, uh is the card holder. I’ve stopped carrying bill fold wallets and I kind of use a card wallet with some spare cash, pretty much exclusively. So, when we designed the new Fort Belvedere card carriers, it was a no-brainer for me, and I actually use a second one as a business card case, just because it’s nice and easy. Uh you can get the card out easily quickly. Exactly. It fits in a pocket.

[Raphael] Yeah, they’re not bulky. That was part of the design just to help that. Got a card here, and then you’ll have some cufflinks here. Looks like some vintage, some Fort Belvedere collar clips and pins, some… What watches do you got there?

[Jack] So, I typically travel with two to three watches as a maximum. Today, I’m wearing my Cartier Tank, a very special watch to me; sentimental. My friends and family got together and purchased this for my 30th birthday.

[Raphael] That’s cool!

The Cartier Tank is wearable and allows you to wear it with everything.
Jack packed his Cartier Tank.

[Jack] It’s yeah. It’s an awesome piece. This one is kind of my jack-of-all-trades watch. It’s a JW Benson. It’s mechanical wind, so you’ve got to wind it up. But I invested in a couple of removable leather straps, so depending on what leather I’m wearing, I can change the strap accordingly.

[Raphael] With it. Yeah, that makes sense. Then, of course, some Altoids. I mean, how could you travel without Altoids?

[Jack] Exactly. Yep, it’s just one of those things being conscious of other people. We’re in Italy. They like heavy lunches, lots of garlic, lots of truffle. They’re necessary.

Conclusion

[Raphael] Awesome. Alright, so that was it Jack and what he packed. We’ll also do a video about what I packed for Pitti Uomo, which is quite a bit different, I also have different circumstances, and uh we’ll do a little video about what we acquired here, what we’re going to bring home. So, stay tuned for that. And yeah, what do you think of the format?

[Jack] I really enjoyed doing a video like this. As I write scripts for the channel, it’s a lot less work for me. Do let us know if you’ve enjoyed this, if we could do something like this again, what would you like to see.

Reader Comments

  1. Enjoyed this video a lot ! Great to see knowledgeable experts expound on the fine points of matching men’s apparel.

    1. Thank you, Douglas! This was a lot of fun for Raphael and I to put together, so I’m glad you enjoyed it.

  2. Jack comes across like a poser. He tries too hard and it looks that way.

    Rafel looks like he is putting on a lot of weight with his dad body. He better be careful or he’ll be visiting the tailor for alterations!

  3. Great video. Thank you. I would have loved to see how you packed all this and your specific choice of luggage. Thanks.

Comments are closed.