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Chris Modoo of Urbane Outfitters
Chris Modoo of Urbane Outfitters
Required Reading

Menswear Experts Share Their Most Important Rules of Men’s Style

February 1st, 2023

Influential menswear voices drop some important knowledge

At the recent edition of Pitti Uomo, the biannual menswear trade show in Florence, Italy, we caught up with more than a handful of menswear’s most knowledgeable and influential voices to ask them one simple question: what is the most important rule of men’s style?

Justus Hansen, Menswear Influencer

Justus Hansen Men's Style Influencer

To me, the most important rule of men’s style is being true to yourself and staying authentic because everything else is fake, seems fake, and that’s when you lose your character too.

Chris Modoo, Urbane Outfitters

Chris Modoo of Urbane Outfitters

The most important rule of men’s style–and it’s non negotiable–is clean shoes. I don’t care how long your tie is or how wide the lapels are–it’s fashion–but something that never goes out of fashion is caring for your shoes. It shows respect. It shows you look after your clothes. And it lifts an outfit. I think if you’ve got last season’s suit on our you’ve got an old classic suit on, a pair of beautifully polished shoes says a lot about your personality.

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Christopher Korey, CKC New York

Christopher Korey of CKC New York Stefano Bemer

The most important rule of men’s style, I would have to say, is authenticity. I feel if you’re authentic to who you are your clothes get worn with ease.

Jamie Ferguson, Photographer

Jamie Ferguson menswear photographer jkf_man

Tricky one, man. The most important rule of men’s style, for me, is always you’ve got to be comfortable with yourself and you’ve got to enjoy what you’re wearing. I think as long as you have that and you’re confident with what you’re wearing you can wear anything and you’re going to look good in it. Obviously there’s going to be a lot of other stuff you can look into after that, but as long as you’re confident and you like what you’re wearing, that’s it, man! That’s all you need!

Peter Zotolo, Plaza Uomo, @urbandcomposition

Peter Zotolo of Plaza Uomo and urbancompositon on Instagram

The most important rule of men’s style is really hard to narrow down, but if I had to, I would say three: proportion, color, and scale. And I think men of any body type and any shape can use those three elements to find something that works for them.

Nick Wooster, Brand and Retail Consultant

Nick Wooster's most important rule of men's style

The most important rule of men’s style is to–first of all, don’t do what I do…–but always default to the most classic and never underestimate the power of navy blue.

Andy Poupart, @styleafter50

Andy Poupart of styleafter50

The most important rule of men’s style is fit and understanding what fit means. You see folks who are trying to dress better and they make simple mistakes–their jacket sleeves might be too long or too short. Same with their trousers. You see folks with their trousers sort of puddled around their ankles. Those are easy things to fix and will make your clothes look better on you. And then, people make the mistake of wearing clothes that are too tight–or too loose–but usually too tight. Understanding what fit means for you and your body and how you want to look is, I think, the most important thing. Everything else flows from there.

Karl-Edwin Guerre, No Chaser Magazine

Karl-Edwin Guerre of No Chaser magazine and Guerrisms on Instagram

Be true to yourself. Everything else falls into place. Once you’re true to yourself you’ll understand your colors, you’ll understand what works with you, what doesn’t work with you, whether it’s fit, color, or patterns. And once you understand that and you’re true to yourself, you’ll result and do everything correctly.

Angel Ramos, Angel Ramos New York

Angel Ramos of Angel Ramos Bespoke

The most important rule of men’s style is to–whatever you wear, whatever style or world you see yourself in, aesthetically speaking–is to wear it with confidence, with integrity, and just make sure that at all time you know that it is you who’s wearing it, it’s your personality, and don’t care what anyone else thinks.

Fabio Attanasio, TBD Eyewear

Fabio Attanasio of TBD Eyewear

The most important rule of men’s style–I don’t know if there is only one–but, for sure I would say, you must feel comfortable with what you’re wearing. The secret of bespoke–I’m a bespoke enthusiast–is to feel comfortable because bespoke is all about fit. So, study the rules, try to interpret them, and adapt them to your style, and feel comfortable with what you’re wearing.

Michael Williams, A Continuous Lean

Michael William of A Continuous Lean and ACL Golf

The most important rule of men’s style–I’m glad you asked this question–is that there are no rules. And I think that you see that here at Pitti here in Florence. Everyone’s sort of following what inspires them. And so, I think, let go of all the constraints I think people have and just feel free to express yourself and dig into what makes you feel like the best version of yourself.

Mitchell Moss, Menswear Musings

Mitchell Moss of Menswear Musings

The most important rule of men’s style I would say is fit–but that’s closely tied to silhouette. Because a well-fitting jacket, a well-fitting pair of pants–if you’re going for a slim or even a traditional fit you don’t want it to be too baggy. But sometimes you want a little more drape in the chest or something like that. But a jacket that’s too big is still too big. So fit is key within the confines of the silhouette that you’re trying to go for.

He Spoke Style

Over the past 10 years, He Spoke Style has established itself as the leading online destination for premium original men’s style content. Blending information and inspiration, He Spoke Style provides practical style advice, outfit ideas, product reviews, and trend analysis for regular guys interested in menswear. Known for their relatable and distinctly unpretentious voice and approach, Founder Brian Sacawa and his team of writers have become influential in the contemporary menswear conversation, having been quoted and featured in publications such as The New York Times, Wall Street Journal, Business Insider, Esquire, GQ, The Robb Report,, Playboy, The Rake, and The Huffington Post.

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