Five Menswear Insiders on Fashion Week ’Fits and “Street Style Dressing”

Jun 09, 2023

By José Criales-Unzueta

There’s no fashion—or street style—season like the menswear shows in the summer, or so I’m told. Something about that June sunshine and the relatively light schedule—it’s smiles all around. Nowhere is this more evident than in our street style coverage, where folks seem just as relaxed as their looks.

This will be my very first season traveling abroad for the shows. I’ll be joining the pack in Paris tomorrow, and, as you can imagine, I spent most of last month thinking about what I would pack for this little adventure. Rather than continuing to spiral in front of the mirror, I reached out to five recurrent faces in our street style galleries. These stylish friends—among them two editors, two stylists, an influencer, and a model—are used to globetrotting from fashion week to fashion week, so I asked them about their own packing and outfit-planning rituals.

They gave me some good tips, so be sure to read through and learn a thing or two. And come back for our spring 2024 menswear coverage as the Paris leg of the collections begins.

New York, 2023.

Paris, 2022.

How do you generally approach putting together an outfit, and does that change at all during fashion week?

I tend to just wear whatever I see in my wardrobe, and whatever arrived last is the key piece for that day or week. Basically the newest piece I shopped for or received becomes the guide for my looks. But more than anything I’m very chill, I never wear uncomfortable things. If I have to shoot something I’ll go for a look, but on a daily basis I’m pretty easy. I love my Carhartt, and bags are my thing. But during fashion week, it’s a different game. It’s performance time! I try to not go for full looks or wear things I wouldn’t wear otherwise, and I mix things I take from fittings and from whatever I packed. The most important thing is to do fittings if you’ll wear something from a brand. If you go with pre-selected looks it’s a mess because you can’t do your own thing and end up in a head-to-toe runway look. The important thing is to bring your own shoes, because some brands are bad at making real shoes for runway collections. It’s the ugliest shit on the runway. I can’t go running around Paris in astronaut boots [laughs].

I used to plan all the time. But it’s been 10 years now, which is crazy. I was that person running around with four luggages and all the looks planned from home. I used to shop before going to fashion week. But now, the way to keep it fun for me is to bring stuff that I know makes me feel comfortable and more myself. And then once I arrive in the city I’ll do fittings and work on the look with the people from the brand I’m working with. I need to know if it’s going to be cold or warm, if I’m going to sweat or not, if the show is indoors, etc. If it’s indoors I can be classier, but if it’s midday and outside then…I’m going to be naked [laughs]. I like things to be more spontaneous, if I plan then the stress is not good for me.

I’m traveling to the shows for the first time this season. What packing advice do you have for me?

I can tell you’re a planner. You don’t have time for the unexpected. My advice is that it’s so hectic already that you should never overpack. Bring whatever basic things are comfortable: Pants, tank tops, t-shirts, a black blazer, etc. All those things that you know you’re going to look for when you want to style something more special. You need to bring the stuff that works with everything, the most versatile things that you have, and then work with the new or special stuff that you borrow or want to bring. I used to pack everything. I would go around with 30 pairs of pants and so much shit I never used. It made no sense.

How has your style evolved since you first started attending shows? Is there anything you used to do at the beginning that you have stopped doing since?

Wow. It’s been everywhere, I’ve done everything. I’ve been the boring, all-black person, the full look person, I’ve had my naked era, the oversized era. I’ve been through so many directions and it keeps changing. I think that what I like about style and clothes is that they allow you to evolve with them and not be tied up to something because that’s “who you are.” I’m not about doing one single thing, but it’s about how I feel at that time and on that day.

What about your clients? How do you approach styling someone else for the shows?

I don’t pack for them. It’s true that for some people it works, and sometimes I have things that work for them and sometimes I’ll use it, but I don’t think of it that way. It’s really so much easier to dress people than it is to dress myself. I’m in contact with brands and they send me options, and I know what works for someone and what they’re going to love. Then you just do the fitting and work through the look. Some people I work with already have their own style, and maybe we’ve built it together, but they do. So the direction is already there.

What is your point of view on “fashion week dressing,” so dressing a certain way just for the shows/street style

I love people dressing up, and I love people wanting to go to a show and look cute. I also love it when people know what looks good in a street style picture. I think it’s part of the game, and it’s fun and creates so much content. Influencers do it, Rihanna does it, everyone does it. As long as there’s style, and as long as there’s a point of view, I love it. It can be lowkey or crazy, but as long as it’s you I’m all for it.

Milan, 2023.

Milan, 2023.

How do you generally approach putting together an outfit, and does that change at all during fashion week?

For me it’s important to be as authentic as possible, which is why my style, whilst constantly evolving, has fundamentally remained unchanged for the best part of a decade. The foundations of my own personal style lay within three distinct groups: cut, color, and texture. I gravitate towards one core color, or tonal variants thereof, whilst simultaneously mixing in subtle textural elements to add richness and depth.

The cut should first and foremost be complementary to my body shape, and secondly it should be dynamic in design terms. I tend to lean toward either sharp structured garments or louche voluminous ones. At times I interchange the two to play with proportion.

Would you say your style during fashion week is reflective of your everyday style, or do you tend to experiment more during the week?

Whether I’m at home (in London), or in Paris, Milan, or New York, I will always try to make the same conscious decisions when it comes to getting dressed. My preference is to reference the past, whilst simultaneously embracing the present. I am a huge fan of classic tailoring, but my approach to dressing isn’t always what you might call “conventional.” Yes, I wear suits with shirts and ties, but I will often choose to deconstruct the notion of what tailoring is, opting to juxtapose the formality of a suit with softer more contemporary accessories.

How has your style evolved since you first started attending shows? Is there anything you used to do at the beginning then that you stopped doing since?

I think for me it’s been a case of evolution not revolution. I understand what works for me, I’ve refined my tastes and preferences to a point where I’m focused on a perennial timeless style. That has allowed me to build a wardrobe that exists as an interchangeable capsule, mixing and matching designer with craft and heritage wear. I haven’t really stopped doing anything in particular other than wearing new shoes. Everything I wear on my feet has to be broken in. I’ve learnt that the hard way!

What is your point of view on “fashion week dressing,” so dressing a certain way just for the shows/street style?

My first show season was in 2011 and I can vividly remember standing at the exit to the show space after walking for Oliver Spencer, lighting a cigarette and hearing the shutter of a camera. I was wearing an oversized Hawaiian shirt; some suit trousers (with a rip in the knee) and my old Vans. Nothing revolutionary, but the moment was captured by Tommy Ton and the image appeared on the homepage of Style.com. At the time, I was still practicing as a Solicitor and didn’t really have an understanding of the fashion ecosystem. This was my first introduction to the notion of “street style” and its importance to industry.

For me, the way you dress should be a natural reflection of your personality. It shouldn’t be contrived or stage-managed, it should be you or an iteration of you. I genuinely love the coverage of the street as much as I love the coverage of the runway. What people are wearing outside the show is just as important to the zeitgeist as what is being worn on the catwalk. Regardless of my own personal taste, I can appreciate each and every person and the moment they have created. It’s a wonderful melting pot of individual style.

New York, 2023.

Paris, 2023.

What is your point of view on "fashion week dressing," so dressing a certain way just for the shows/street style?

From an inside perspective, I see the narrative behind why someone would dress a certain way just for shows/street style. Aside from there being a notion of predictability that comes with fashion week, I feel that so many of us see fashion week as a form of escape from our normal lives, and with that comes the freedom to reinvent yourself, even if it is just for that one week or for that one photo captured.

Do you have any style and/or packing hacks when it comes to dressing for fashion week events?

Packing cubes. I recently came back from holiday, and I was introduced to packing cubes, and I can wholeheartedly say I will never pack for another trip without them. They keep everything so organized and condensed, and make for seamless packing. I also feel like doing a big style-out, then refining that style-out down to pieces that you actually will wear during the events, dinners, and such.

I mostly feel that fashion week is a direct reflection of my everyday style with a little bit more consideration, if you will. It’s also doing a fashion week packing that I find myself unpacking and rediscovering pieces in my wardrobe, that I actually adore, just haven’t reached for in some time.

How has your style evolved since you first started attending shows? Is there anything you used to do at the beginning then that you stopped doing since?

I remember when I first started attending fashion weeks, I felt that there was a sense that I had to prove myself to the fashion community that also attended fashion week so my intention was to build looks for other people’s approval, rather than my own. That quickly fizzled out as I began to step into my own sense of style and comfort in the way that my style made me feel.

Paris, 2023.

New York, 2023.

Do you plan all your fashion week outfits ahead of time, or do you tackle it more organically?

I think the main difference is the fragility or delicacy of the clothes. Things I’d wear to a show are not the same aswhat I would wear to the club or to be out during the day. But overall, I love an element of suiting, and that stays consistent during or outside of fashion week. During the week I’ll dress it up a little more with jewelry, gloves, and other accessories, and shoes. I always try to plan for looks but keep things open, because you never know how you’ll feel the day of.

When I’m packing for Paris, I definitely have a slew of looks I’ll try to style as great as possible and then take pictures. I text the photos to my best friend Tyrone, who lives in Paris, and he’ll give me his honest opinion. Always ask your close friends, they’ll tell you when something is shit [laughs].

Do you shop specifically for fashion week or tend to borrow clothes from brands?

I’m 50/50 when it comes to wearing my own clothes versus borrowed pieces. I have things of my own that I cherish and want to have as the focus and tend to save for fashion week because I want people to see them, and then sometimes it happens that someone wants to make something for me or dress me, so I do that too. When it comes to borrowed pieces, though, I like mixing and matching. Even when I get invited to a show and the brand wants to dress me, I like to mix it with something else so it still feels like myself.

I don’t shop for fashion week, but I do keep fashion week in mind when I shop throughout the year. I am definitely a sale queen, and I don’t really buy things full price unless it’s an item I know I’ll never see again. The more special a piece is then the more likely it is I won’t wear it until a fashion week event, because that’s when I like to dress up the most and when people pay the most attention, so it feels worth it.

How has your style evolved since you first started attending shows? Is there anything you used to do at the beginning that you have stopped doing since?

My first show must have been a little over 10 years ago. My style has changed so much over the years. Back then I was obsessed with A.P.C. petit standard jeans, Prada brogues, and would always wear a Missoni button-down shirt or something like that. I loved having suspenders, and had this big bow tie the guy I was dating at the time gave me, and also round circular glasses. So it’s definitely a full 180 to what I am now, which is basically a fashion leather daddy fantasy.

What is your point of view on “fashion week dressing,” so dressing a certain way just for the shows/street style?

I personally try not to do it. If I get my photo taken, then great, I’m glad someone gets it, but it’s not something I think of when getting dressed. But also, I’m not going to judge someone that does it and who wants to get dressed up specifically for that moment. It also has a lot to do with people’s individual brands. Street style has become almost like a mini press tour for yourself and your brand, and so I think it lends itself to what you want to do for yourself. What’s cool about it is that there are a lot of people every season that you may not acknowledge until you see them wearing this crazy thing, and that allows for conversation and meeting other people. But overall, for me, it’s about feeling good and confident, that’s the goal. If there’s a photo, then cool.

Paris, 2023.

London, 2023.

Do you plan all your fashion week outfits ahead of time, or do you tackle it more organically?

I have to plan my outfits, otherwise I will be a nervous wreck in the mornings before a show and probably late. I’ll pack the clothes as outfits, and keep an idea of what goes with what item in mind, but I’m happy to play around with what I’ve brought (and inevitably bought on my travels) once I am actually facing getting dressed in the morning.

Trousers are bulky, so pack less of these and keep them as core staples that work with a multitude of tops, which are easier to pack. One or two foolproof coats come winter, ONE bag, TWO shoes—one sneaker, one more formal. The trick is to minimize the amount you’re bringing, while maximizing the mix-and-match-ability of it all.

Would you say your style during fashion week is reflective of your everyday style, or do you tend to experiment more during the week?

It's totally reflective. With all this being said, I actually do not “dress up” for the occasion. I’ve worn suits to K-WAY, and a T-shirt to Dior. Who cares?

How has your style evolved since you first started attending shows? Is there anything you used to do at the beginning that you have stopped doing since?

I think since I’ve been attending the seasons more often, I’ve inevitably picked up styling cues from the runways that I try to input into my day-to-dress dress sense. I don’t know what those styling tips might be, per se, but it’s definitely enabled me to explore what does and does not work for me on a more elevated level.

What is your point of view on “fashion week dressing,” so dressing a certain way just for the shows/street style?

Yeah, that’s quite meh. Tacky. Be yourself, who are you trying to impress?