The Mind-Boggling Style Evolution of Menswear's Biggest Stars

Do you know what some of your favorite menswear's stars thought was poppin' in the streets back in the day?

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Complex Original

Image via Complex Original

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If there's one constant in life, it is change. We may tout the notion of classic, timeless style here, but the reality is that dudes change the way they dress, both out of a personal desire to evolve and develop, and also just cause that's just the name of the game.

Magzine editors, power bloggers, designer, even rappers have a reputation to uphold when it comes to being stylish and staying on top of the trends of the times. That means they have to be able to adapt their personal style and stay ahead of what is cool now so they can appropriate what will be cool in X amount of time. Taking a look back, the style evolution of the biggest stars of menswear is quite astonishing. Take a jaunt back to #menswear style of yore with The Mind-Boggling Evolution of Menswear's Biggest Stars.

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Stephen Mann

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What He Used to Be: Style Disciple
What He is Now: Japanese Designer Meets Jesus

Stephen Mann has run under the radar of menswear for a couple of years now, emerging as a stylist who knows men's style better than, like, 99% of the world. Menswear forum members knew him as "seenmy" in the mid-2000s, introducing the world to clean outfits with Supreme, visvim, the Soloist and more favorites you were unaware of a few years ago. Now he's getting street styled where ever he steps foot because of his unique take on Japanese designs and Jesus-like mane.

JR Smith

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What He Used to Be: Streetwear Victim
What He Is Now: The Earl of NBA Style

Sure, his NBA career may currently be in jeopardy, but JR Smith may have a new career as a street style star. The New Jersey product has come a long way from overly baggy clothing and minimal tats. Improving to CDG Play, Public School and Michael Bastian has JR among the best dressers in the league.

Josh Peskowitz

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What He Used to Be: The Source
What He is Now: The Kimono Kid

The style maven currently known as "Pesko" is one of the unsung heroes of menswear today. His unique twists to what is deemed cool only accentuates the actual coolness. He has worked on a couple of different stages, ranging from hip-hop magazine Vibe to retailer Gilt, so he's taken a little from both avenues, tossing street and formal wear together for a look that's hard for anyone else to really pull off.

 

Glenn O'Brien

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What He Used to Be: The Fuckin' Man
What He is Now: Checking...Yep, Still the Fuckin' Man 

Glenn O'Brien is a legend and a pioneer in the subcultures and scenes that made NYC the coolness capital of the world. His impact on art and style dating back to the '70s is truly remarkable. The rebellious nature of O'Brien's style has been tamed a bit over the years, even as he's contributed to GQ as "The Style Guy." But nonetheless, Glenn can go from dapper to grunge and pull off either look with the best of them. No style evolution has been more zen.

Lawrence Schlossman

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What He Used to Be: Southern Hospitality Bro
What He Is Now: Fashion Bro

Lawrence's started blogging from the bottom and now he's at the tippy top as EIC of menswear's own self-deprecation headquarters Four Pins. He's also been a street style star since lord knows when, getting photographed in Florence to NYC transforming from menswear bro to sprezzy bro to cozy bro.
 

Josh Kissi

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What He Used to Be: Street kid from the Bronx
What He Is Now: Globetrotting Style Maven

It doesn't take much to start a blog that captures your personal style. But Josh Kissi and Street Etiquette partner Travis Gumbs did so at the perfect time in the mid-2000s. His penchant for finding classic treasures while thrift shopping and giving tailoring them to perfection wasn't always his go-to. The NYC street scene and fashion forum browsing spurred his love for menswear and he decided to create his own lane from it. 

Eugene Tong

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What He Used to Be: Menswear's Archetype
What He Is Now: Menswear's Beacon of Hope

Eugene Tong has easily emerged as one of the best dressed men on the planet. The Details Magazine editor's effortless style is constantly documented all over the world. When people first began noticing his style, it was definitely because he embodied all that menswear had going for it. Now, he's known more for seamlessly combining streetwear staples and designer grail pieces to create a look that isn't easily replicated, no matter how often aspiring modern-day style icons try.

 

Nick Wooster

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What He Used to Be: "Who's that dude that's all tatted up and always wearing a suit with boots?"
What He Is Now: "That Dude"

Did Nick Wooster exist prior to 2009? According to his resume, he's be doing the damn thing since the '80s with the likes of Barney's, Bergdorf Goodman, Ralph Lauren, and plenty more high profile menswear names. But according to photos, he became the Woost Gawd around early 2010 and has been thriving ever since. While his style hasn't changed too drastically, the biggest change has been his toe-dipping approach to trends. One flick and you're likely never to see that piece, or the style it's worn, ever again.

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