The 50 Most Stylish New Yorkers Right Now

50. Spike Lee

Occupation: Filmmaker

Spike may have made some questionable style choices in his day, but he earns a spot on this list through unapologetic commitment to New York, loud sneakers, and the retro style that he helped make iconic in his films. Without Spike, there’d be no Mars Blackmon and no Mookie, and that, friends, would be a sad, sad world.

49. Steven Rojas

Occupation: Social Media Director, GrandLife Hotels

It's possible that Steven Rojas is the quintessential Manhattan cool guy. Sure, he dresses impeccably, and can make a T-shirt and jeans look as classy as a suit, but his wardrobe simply complements his natural charisma. You meet the guy and just think he probably does fun shit all day. He's done stints at fashionable showrooms like Archetype before landing his current gig as the Social Media Director of GrandLife Hotels. Now he gets paid to look classy and rock out at parties in New York and Paris. Tough life huh?

48. CurT@!n$

Occupation: Rapper

CurT@!n$ emerged as a trendsetter as soon as Kanye called him a "fashion genius" in Complex's 2007 April/May issue. Think Kid Cudi put vintage leather jackets on the map? CurT@!n$ did it first. Dior Homme denim? He was on those early. The '90s shirt-around-the-waist trend that all the cool rappers are doing these days? CurT@!n$ did it a year before those guys finally caught on. His name might not be on your list, but best believe he's inspiring the dudes that you look up to.

47. Henrik Lundqvist

Occupation: Goalie, New York Rangers

Being one of Sweden's most desirable exports isn't enough for someone considered to be the premier goalie in the NHL. Henrik wears the hell out of slim, modern suits. So much so in fact that DKNY has enlisted his services as a brand ambassador. No matter what happens in the playoffs, we think Lundqvist already won a place in hockey's style hall of of fame.

46. James Jean

Occupation: Blogger, The Mod Rockers/Freelance Stylist

Blogger James Jean came up around the same time as contemporaries like Josh Kissi and Travis Gumbs of Street Etiquette, and has consistently had a subtle, understated style. Whether doing special projects for companies like Tretorn and Rugby, or simply getting dressed to run errands, he maintains an effortless balance of casual and unique without looking like a peacock. Don't get it twisted though, he still knows how to turn things up to 11 when the occasion calls for it. It's high time he got his shine.

45. Marcus Samuelsson

Occupation: Chef, The Red Rooster

The Ethiopian-born, Swedish-raised chef has been mixing tribal elements with European flair from day one. So of course that carries over into how he dresses himself. Often seen in well-fitting wardrobe staples, he takes things to a different level by juxtaposing a simple sweater with a printed scarf. Recently, we spotted him giving a pair of chinos and button down a pop of color with a pair of red sneakers. The guy clearly knows what he's doing.

44. James Wilson

Occupation: Blogger, Secret Forts

There are certain guys that just live it. This applies to bloggers as well. James Wilson's influential digital presence, Secret Forts, is only surpassed by his actual one. This stylish jack of all trades leads the way for his fans and imitators alike. We wouldn't sum up James' look as simply "Americana" — that would only tell half the story. Dude can rock a pair of J's as easily as he rocks a pair of Red Wings, or whatever boots are going to be all the rage six months from now.

43. jeffstaple

Occupation: Founder/Designer, Staple Design

In what seems like a scene from"How To Make It In America," jeffstaple's career took off when he walked into a Triple Five Soul store in 1997 wearing a T-shirt of his own design. The manager dug it so much he placed an order for 12 right then and there. Later that year, Staple Design was established, with the Reed Space boutique opening up in 2002. Far from being done, staple would cement his place in New York streetwear's legacy when he designed the infamous Nike SB Pigeon. As far as style's concerned, jeffstaple's got it in spades. Decked out in the epitome of Lower East Side cool, he isn't afraid to switch up his T-shirt game into tailored button downs, knitwear, and colorful parkas.

42. Adam Kimmel

Occupation: Designer, Adam Kimmel

Many of the best-dressed menswear designers in New York have a consistent, understated approach to style. Adam Kimmel is one of those dudes. His collections tend towards the classic, but his presentation is often anything but. He’s designed a collection inspired by Snoop Dogg, shot a lookbook at a rodeo, and staged a shoot with David Blaine, fitted in a Kimmel tux, swimming with sharks. So, even though his look may fall into the “cool dad” category, he still knows what he's doing.

41. Jimmy Fallon

Occupation: Comedian/Host, Late Night With Jimmy Fallon

It’s hard out there, sartorially speaking, for a late night host. He can’t alienate his viewers (all of America), but he’s still gotta be interesting and charming enough to hold our attention. David Letterman held things down for a few decades or so, and Conan and his hair are definitely attention getting, but Fallon’s perfectly tailored suits, surprisingly charismatic wit and shit-eating grin take the cake. 

40. Mordechai Rubinstein

Occupation: Blogger, Mister Mort

Mordechai Rubinstein started out as a New York shop guy before working his way through the fashion industry, eventually landing a cush position as the Associate Market Editor of Men's Vogue. After the publication's demise, he took to blogging street style photos at his site, Mister Mort, before getting a cool gig with Levi's. Known for his hilarious twitter criticism of modern trends and menswear, his personal style channels Americana and New York vintage culture perfectly. He nerds out over L.L. Bean duck prints and well-worn 501s, yet hates tight pants and dudes that are too handsome for their own good, and for that, we salute him.

39. Justin Theroux

Occupation: Actor

Name one other guy in New York, no, the world, that has both collaborated with Moscot and had sex with Jennifer Aniston (arguably America's national treasure). Exactly. Justin Theroux is in a league all his own.

38. Scott Campbell

Occupation: Tattoo Artist

He’s not just a tattoo artist, he’s a celebrity tattoo artist, and his client list includes Heath Ledger, Sting, Robert Downey Jr., and Marc Jacobs. In fact, Marc Jacob’s liked Campbell’s work so much that he’s hired him to do more than just his body ink. How many tattoo artists can claim a Louis Vuitton bag design and runway show credits? Campbell is also the main force at one of NYC’s best tattoo Shops, Saved, in Brooklyn.

37. Jake Davis

Occupation: Filmmaker

Jake Davis is a New York-bred filmmaker with a clear eye for style. In addition to his "Test Shots" series, he's also done videos for the likes of Nike, K. Swiss, and Puma. It's no surprise that his keen eye crosses over into his closet, seemingly changing up his look every few months. For a while, it seemed he couldn't be seen in anything but a long coat, tailored sweatpants, and comfortable sneakers. Now, a recent trip to Japan has him decked out in the dopest gear you probably haven't heard of.

36. Patrik Ervell

Occupation: Designer, Patrik Ervell

Patrik Ervell started out as a Political Science major in college, and well, he hasn't quite stopped dressing like a nerd. And by that, he's stuck with a solid uniform, mostly of things he designs himself. The utilitarian edge of his collection reflects his own personal style, which is simple, efficient, yet at the same time not boring, thanks to subtle details like club collars.

35. Morgan Collett

Occupation: Co-Founder, Saturdays Surf

Morgan Collett studied in Italy for a few years before taking a position at Acne, so he knows a thing or two about European sensibility and good style. Maybe that's why the Saturdays Surf co-founder dresses more like the surfers of the '50s and '60s, looking more "Endless Summer" than "Point Break." We wish more weekend warriors would follow suit.

34. Michael Chernow

Occupation: Co-Founder, The Meatball Shop

It takes a certain chutzpah to get people excited about the prospect of piping hot balls in their mouth, but only Michael Chernow did it in style. The restaurateur consistently channels a downtown cool with his untucked flannels and well-groomed side part, which makes sense given his brainchild, The Meatball Shop, started on the Lower East Side.

33. Angelo Baque

Occupation: Brand Director, Supreme

Supreme tends to keep things under pretty tight wraps, so consider Angelo the gatekeeper. Unless you’re a blue chip artist, a downtown legend, or the next best skateboarder in the City, you’re probably not going to get down. His personal style is a mix of patterns and layers from military, Americana and vintage workwear — throw in some Supreme, a fitted, and a pair of New balances and you’ve got that shit on lock. If only it were that easy. Props to Angelo for pulling it off.

32. Woody Allen

Occupation: Writer/Filmmaker

The important thing to note here isn’t just how well Woody has aged into his personal style, but that he can be a style icon for both you and your pops. His look is simple, worn-in, and pretty ordinary, but somehow it’s still unmistakable. And we don’t need to go through the dude’s whole oeuvre to prove that he’s a G (for genius), just trust us, and if you haven’t seen it yet, watch Manhattan. Now.

31. Daiki Suzuki

Occupation: Designer, Engineered Garments

Sartorial fact: old Japanese dudes are always swaggy. Not only is Daiki the head of Engineered Garments, one of the best brands to come from the workwear crazy of the last few years, but he wears it better than anyone. Expect to see Daiki mixing classic pieces from his brand like tweed blazers and button-down oxfords with some of the sartorial oddities he produces, like shin-length knickers and hooded dickies. This is double black diamond style, kids. Experts only.

30. Tyson Chandler

Occupation: Center, New York Knicks

Ask New Yorkers who the most stylish basketball player is and they'll say Amaré Stoudemire or Carmelo Anthony. Amaré's too obvious a choice with a well-known stylist by his side and his publisized friendship with Anna Wintour. Melo is on everyone else's "Most Stylish" list and is also a strong contender. However, we're going with Tyson Chandler. The Knicks center flies under the radar but is actually fashionable on the low. Just check his affinity for fitted plaid shirts and the courage to go with a spread collar.

29. A-Trak

Occupation: DJ

Alain "A-Trak" Macklovitch made a name for himself when he won three major DJ competitions. In 2004, he blew up when Kanye West recruited him as his personal tour DJ. Since then, he's continued to make musical waves with his label Fool's Gold, as well as aligning himself with iconic, streetwear-friendly brands like Nike, New Era, and Kid Robot.

28. Philip Crangi

Occupation: Jewelry Designer, Giles & Brother

To design some of the most sought-after jewelry in NYC, you need to have an understanding of aesethics. Much like his line, Giles & Brother, Crangi is equal parts rugged and refined. Look no further than his grizzled, yet perfectly manicured beard. Often cited as a young doppelganger for street style superstar Nick Wooster, this Nike Air Max collector holds his own.

27. Sean Sullivan

Occupation: Photographer/Curator, The Impossible Cool

Who would have thought a guy could build a personal brand from posting black-and-white photos of old white dudes? Well, mostly white dudes. Sean Sullivan's "The Impossible Cool" tumblr is a great source of inspiration for timeless style, which Sullivan exhibits himself. Often outfitted in simple, well-fitting garments, Sullivan seems to be grooming himself to be as classically handsome as the men whose photos he posts.

26. Thom Browne

Occupation: Designer, Thom Browne

Thom Browne reinvented the way men in America wear suits. How’d he do it? He let his personal style lead the way. But it’s not just the extreme tailoring, shrunken suits, and sockless look — his oxford shirts are favored by some of your favorite rappers, and his collaboration with Supreme proved that his brand has plenty of cross-over appeal.

25. Ian Bradley

Occupation: Stylist

Have you ever looked at someone and just straight-up felt depressed because you would never be that cool? Yeah, that's what happens when you look at Ian Bradley. The stuff he wears just looks so dope on him. He's mastered layering and wears a few easy pieces so, so well. Not bad for a guy who isn't a professional model, what he does do though, is style for clients like Uniqlo, Vice Magazine, and The Fader. Sometimes you can find him running the door at The Standard too, so it's obvious he can tell who's really got their style game on lock. Roll up in bootcut jeans and square-toed shoes? Not a chance in hell, bud.

24. Richard Chai

Occupation: Designer, Richard Chai

Cutting his teeth under designer Marc Jacobs, Richard Chai's eponymous label is known for successfully balancing the line between high-fashion, streetwear, and casual shit normal dudes would rock on the regular. That's actually an apt way to describe his own sense of personal style: a grunge sensibility that's been perfectly tailored, yet kept purposefully unkempt.

23. Bruce Pask

Occupation: Style Editor, The New York Times

Bruce Pask's personal style is simple enough. It's pragmatic, versatile, and doesn't look out of place in Paris or New York, but there's always one signature style cue he's become known for: draping his jacket over his shoulders. He's claimed it's a temperature thing, but we can't count anyone else who can pull this off on one hand.

22. Chad Muska

Occupation: Skateboarder/Artist

The Muska. If you know, you know. He was an icon in the '90s when he was charging handrails on a skateboard with a boombox in his hand, and he’s still making a mark today, creating hype-worth sneakers for Supra, making art, and rocking some pretty sick goth-ninja-meets-fashion-hippy steez. 

21. Waris Ahluwalia

Occupation: Actor/Jewelry Designer, House of Waris

Waris designs jewelry and scarves for his own line, House of Waris, but you may recognize him best from various Wes Anderson films. Photographed many times over by street style enthusiasts for his charming style, Waris prefers traditional over on-trend fashion, but never ever looks stuffy. He always looks cool and comfortable, no matter if he's wearing a velvet suit or a vintage tee — which is exactly why he looks so stylish.

20. Angelo Urrutia

Occupation: Designer, Nepenthes New York

Angelo is probably one of the least fashiony guys in the industry, but that's what makes him so special. Eschewing trends, he focuses instead on fit and construction. As the main designer behind Nepenthes' in-house line, inspiration has come from the kinds of clothing you would find at K-Mart (checked flannel shirt jackets with jersey knit hoods), to just using the craziest fabrics he can find (golf jackets made in psychedelic floral patterns). Despite his eclectic taste, you'll usually find him decked out in denim jackets, Yankees hats, and at times even using mesh tank tops as an undershirt. The only thing more on-point than his style? Probably his "Street Fighter II" skills.

19. Maxwell Osborne

Occupation: Designer, Public School 

Maxwell Osborne and his Public School  co-conspirator, Dao-Yi Chow, are helping bring back, and redefine, NYC's downtown cool. What exactly does that look like? Well, one needn't look much further than the man himself. Maxwell can typically seen rocking the all black everything look with a clean pair of shades. And if that singular dreadlock thing takes off, we might as well start calling it The Maxwell Osborne.

18. Justin Doss

Occupation: Fashion Editor, GQ

To find a picture of Justin Doss, just look for the man in a hat at any Fashion Week. Honing his skills down south at Sid Mashburn, Justin headed up north where he began buying for Barneys New York. He built a reputation as one of menswear's young, rising stars and it wasn't before long that GQ came calling. He replaced longtime editor and magazine veteran Lisa Cohen when she retired and is now Creative Director Jim Moore's right-hand man when it comes to tailored clothing. Mr. Doss' greatest sartorial skill is the pure effortlessness with which he wears his clothes. From a simple blue linen sportcoat to an ensemble featuring a variety of styles, no one seems as comfortable in their wardrobe as Mr. Doss. The takeaway? If you're going to wear it, don't just wear it — own it.

17. Dave 1

Occupation: Musician, Chromeo

As the lyrics to Chromeo's "Mama's Boy" say: "She wants a man who's got his game locked tight." And holy shit does Dave 1 have it on lock. The more stylish half of Chromeo, Dave Macklovitch has seen his share of fashion features, including one for Complex with his younger brother, A-Trak. He really knows how to nail that line between classy and casual. Leather motorcycle jackets with a tie? Suits with casual loafers? He's done it, and done it well. Plus, he's got a Ph.D. in French Literature from Columbia. Is there anything this guy can't do?

16. Tom Wolfe

Occupation: Writer

Now’s not the time for a literature lesson, so let’s get straight to the point. Tom Wolfe is the old man we should all aspire to be. He’s got a finely tuned, unique perspective on style. Nobody can fuck with that. When you’re old and brilliant and wildly accomplished beyond your craziest dreams, the absolute best you can hope for is to have a sliver of the steez he’s got. Oh, that and he’s written fifteen books, including “The Electric Kool-Aid Acid Test”, which pioneered an entirely new school of journalism. So, that too. No big deal.

15. A$AP Bari

Occupation: Founding Member, A$AP Mob

A$AP Bari is one of the people that started A$AP Mob, along with childhood friend A$AP Yams. Born and raised in Harlem, he's been spotted at fashion events from as early as 2009, when a picture of him was snapped at an Oak party. Since then, he's allegedly the one who put A$AP Rocky onto high-fashion designers like Alexander Wang, Raf Simons, and Rick Owens. Judging from his own style and his tumblr, A Toast To The God, it's pretty evident that his own tastes have helped influence the style of the entire A$AP Mob, going as far as designing the mob's custom Nike Destroyer jacket.

14. Mobolaji Dawodu

Occupation: Stylist, The Fader

Mobolaji rarely strays from his uniform — cool hat, glasses, and a printed shirt — but always seems to be the best dressed guy in the crowd. The prints and patterns he rocks — usually bright and African — are so dope that even The Sartorialist has shot him multiple times for his street style blog. When he's not styling fashion stories for The Fader, he acts as a costume designer. You can see his latest work in the 2011 Sundance Film Festival pick, Restless City.

13. Eugene Tong

Occupation: Senior Style Editor, Details

As a member of the Details magazine braintrust, Eugene Tong has represented New York's menswear scene all over the world and it's hard to think of a better ambassador. Tong's ability to combine high end fashion (think Dries van Noten) with downtown streetwear (think Supreme) is his calling card. Just as comfortable in a five-panel as he is a Borsalino, Eugene's been holding it down for the mix and match set for years.

12. Theophilus London

Occupation: Rapper

Theophilus London has quickly made a name for himself as a New York fashion plate. In the wake of Kanye West's immersion into the European high-fashion world, the Brooklyn rapper soon became the token hip-hop icon popping up at New York Fashion Week's dopest parties. His regular ensemble consists of skinny pants, tailored blazers, and usually some sort of retro Jordan sneaker on his feet.

11. Abdul Abasi

Occupation: Store Manager, Nepenthes New York

Abdul first really fell into the fashion world while he was in the army — where he was a respected drill sergeant. After going to F.I.T. on the G.I. Bill and majoring in menswear, he interned with Coogi and assisted then-up-and-coming designer Patrik Ervell before securing his first job as an Assistant Designer at Engineered Garments. When Nepenthes NY decided to open their city outpost, Daiki Suzuki couldn't think of anyone cooler, nicer, or more stylish to represent the company at its flagship store, and eagerly handed the keys over to Abdul. Easily noticeable thanks to his Basquiat-like topknot, he effortlessly mixes together Nepenthes' Americana-influenced clothing with fashion-forward brands like Damir Doma, Maison Martin Margiela, and The Soloist. You've probably seen his face as an Engineered Garments lookbook model, or at Park & Bond's Nepenthes e-shop.

10. Ryan Gosling

Occupation: Actor

The world has seen a few different iterations of Ryan Gosling at this point — and your girl would leave you in a heartbeat for any one of them. Rumor has it that Gosling, unlike most of Hollywood’s most dapper leading men, does it without a stylist. And while that remains to be seen, what we can most definitely see, is that the dude is currently the most stylish movie star we’ve got. Whether he’s rocking the ungroomed look in a tux look on the red carpet, or a cleaned up, casual layered look on the street, dude is killing it. And when he’s not killing it, he’s saving lives and stopping fights in man tanks. Now that’s steezy.

9. Ariel and Shimon Ovadia

Occupation: Founders/Designers, Ovadia & Sons

Twins Ariel and Shimon Ovadia came up in Brooklyn, where their dad hustled his way into building a successful children's clothing business. As they grew up, they developed a fondness for Ralph Lauren gear and worked odd jobs just to cop the goods. The inspiration for their menswear label, Ovadia & Sons stemmed from a lengthy conversation with Mr. Lauren himself during a chance encounter at one of his stores. Their personal style is a combination of timeless menswear staples with a slimmed-down, modern twist. In short: they dress like your grandpa but look like the coolest kids on the block. Swerve!

8. Glenn O'Brien

Occupation: Writer

Glenn O'Brien is more than just "The Style Guy" at GQ, he's a New York institution. He literally rubbed shoulders with Basquiat during his "SAMO" days and pretty much did ratchet shit before "ratchet" was even a word. Case in point: his public-access TV show, "Glenn O'Brien's TV Party," which featured performances from acts like Klaus Nomi and Blondie. O'Brien isn't simply stylish, he never stopped being cool. Even though he's a veteran in the scene, he's still outdressing dudes more than half his age. Can you imagine any other dad wearing Supreme next to Tyler, The Creator and holding his own, style-wise? Yeah, didn't think so.

7. Dao-Yi Chow

Occupation: Designer, Public School

Dao-Yi Chow wasn't always in the fashion game, although it was his stint as a brand manager at Sean John that introduced him to Public School co-founder Maxwell Osborne. Chow had previously been a journalist for publications like Vibe and The Source, and Ego Trip, before diving into the clothing industry with Mecca. His style has always maintained a certain casual downtown vibe, including a variety of slick leather jackets, dark jeans, and baseball caps. It's easy to see how his own way of dress would go on to influence his designs.

6. Josh Peskowitz

Occupation: Men's Fashion Director, Bloomingdales

Show us a more seasoned industry veteran at such a young age and we'll show you a liar. Josh Peskowitz, editor-turned-fashion-director, may know more about men's clothing than anyone on this list. Peskowitz is a menswear chameleon of sorts, pulling off different style after different style in almost every picture that's taken from him. That fact speaks a lot to his eclectic pedigree and is proof that some guys just know what they're doing. Pesko's most impressive sartorial feat may have been a few years ago when a broken foot forced him to rock a cane during Fashion Week. And, you know what, he still killed it. Like The Sartorialist once said, "limpin' aint easy."

5. Brendon Babenzien

Occupation: Creative Director, Supreme

Supreme’s creative director keeps a pretty low profile compared to a lot of other dudes on this list. That’s probably because he’s the man behind the most hyped brand in New York. The best way to describe his style ends up sounding a lot like describing the racks of clothes you’d find in the store on Lafayette. Classic, understated, vintage inspired pieces, mixed with touches of military, outdoors, and prep staples. Brendon’s look seems to hinge on an eccentric mix of layers, perfectly tailored, faded denim, and loafers. It’s not likely that you’ll see him at a menswear party any time soon, but if you did, he’d likely be the best-dressed dude there.

4. Nick Wooster

Occupation: Creative Director of Men's Clothing, J.C. Penney

Most people know Mr. Wooster as the mustachioed badass who has graced street style blogs as much as any of our modern day style icons. Nick's pedigree is as impressive as his blog presence. His love for camo knows no bounds and all those kids that have taken up smoking since he's burst onto the scene, well, that's just a negative side effect of being one of the best dressed men in the world. 

Most notably he was the Men's Fashion Director of Neiman Marcus Group Services (this includes NYC's iconic Bergdorf Goodman) and has put in work at John Bartlett, Ralph Lauren, Calvin Klein, Park & Bond, and Project tradeshow. When news broke that he would be joining J.C. Penney as the Creative Director of Men's Clothing, the fashion world took notice. If there's anyone that can bring a little Milan to your local mall, it's Nick Wooster.

3. Gay Talese

Occupation: Writer

Gay Talese is one of the writers that helped define literary journalism. In his articles for Esquire and The New York Times, he often used writing techniques previously seen only in fiction to bring readers more deeply into the story. Clearly, he's a man who pays painstaking attention to detail. The same can be said for his personal style. Often seen in impeccable suits, everything fits him perfectly. Talese often touted himself as dressing for the story, and ironically enough, how he chose to do so became a story in itself.

2. Jay-Z

Occupation: Rapper

Before you start with the “Jay-Z” isn’t stylish rant, just remember: style is more than just about clothes and money (although, those two things are important). It’s about more than just looking cool, too. It’s a whole attitude and way of life, and that’s why Hov is sitting pretty as the runner-up on this list. His resume of hit records and business ventures make him more than just one of the greatest rappers alive — he’s an icon. 

Kanye helped Jay up his high-fashion game with the Givenchy-dipped Watch the Throne Tour, but before that he enshrined hip-hop style staples like the Yankee fitted cap, wheat Timberlands, and white tees. But his style game runs deeper — name an emcee who can wear a suit better.

1. A$AP Rocky

Occupation: Rapper

A$AP Rocky and the A$AP Mob brought more than just a new sound to the NYC hip-hop scene when he launched a jet-fuel powered career in 2011 with the hit “Peso.” Now 24, from the day the Harlem-bred rapper set his Margiela-clad feet in the game, he’s pushed hip-hop and street fashion in a whole new direction.

Credit Rocky for introducing streetwear heads to their new favorite brand (Pigalle), bringing a fashion industry veteran into a new spotlight (Jeremy Scott), and helping another young designer build on his crossover appeal (Alexander Wang). Jay-Z is the New Yorker that got us here, now A$AP Rocky is leading the way.