Image via Complex Original
That headline may sound basic and rote off the first read, but think about it. How many famous dudes are really out here flourishing in all of life's key arenas? This list of swagless people who are otherwise flourishing in life that we compiled earlier this year could've probably doubled because that population of celebrities somehow outnumbers the alternative.
Dudes with money, fame, access to cheat codes like free clothes and stylists are really out here dressing bummy as fuck, fully reinforcing that old "racks can't buy style" adage. So salute these swag lords for maximizing their potential, stacking up storied hit lists, carrying on high profile relationships with dimes and styling on the rest of the world while doing so. Eligible bachelors only. Read on for 10 Famous Guys Who Date Hot Women and Have Dope Style.
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Nick Young
Notable Partner: Iggy Azalea
The rising star in the west is also leading the pack of new NBA fashionistos, and not just off the court either. He regularly draws the ire of hypebeasts by hooping in the latest riot-inducing kicks, and after that, he goes home to Iggy freakin Azalea. Sure that's only one major conquest to his name, but given how new he is to the spotlight, it's still impressive. So is convincing the population to earnestly refer to him as "Swaggy P." When he backs up the moniker this well though, we can't really object, can we?
A$AP Rocky
Notable Partners: Iggy Azalea, Chanel Iman
At this point, Rocky may be more well known for being the best dressed at any given event than for his music. That’s not a knock on his contributions to the rap game, just an acknowledgment that the Fashion Killa’s out here making serious waves in multiple cultural arenas. That front row fashion show seat just makes it easier to scoop a model off the runway.
Harry Styles
Notable Partners: Taylor Swift, Kendall Jenner
Sure, his jeans may be skinnier than those on whichever celebutante he’s currently romancing, but you really can’t hate on the aptly named Harry Styles. Fashion-wise, he’s lowkey the most respectable boy-band/teeny-bopper star out, and the ladies know that.
Joseph Gordon-Levitt
Notable Partners: Larisa Oleynik, Meagan Good, Alexandra Hulme, Devon Aoki, Phoebe Tonkin, Meighan Bennet, Tasha McCauley
JGL is like, the Barney Stinson of Hollywood's new class. He'll dress down now and then but for the most part this dude is always dressed like he's shutting down a red carpet or taking his girl's parents out to dinner.
If it's not a suit, then he's at least prepped out with an oxford under a pullover. It's the suit game that's given him real #menswear cred though, especially since he's not one to shy away from a typical black-grey-blue rotation and successfully switch it up, with some real vibrant shit. Perhaps it's that suited up look that has the ladies under pressure, but your boy Joe's wins go way back—he even bagged up the OG bae Alex Mack.
Bradley Cooper
Notable Partners: Jennifer Esposito, Isabella Brewster, Renée Zellweger, Olivia Wilde, Jennifer Lopez, Zoe Saldana
With his ever-rising star in Hollywood so too has Cooper's propensity to stay casual grown, especially in the winter when he completes his cypher with fly ass topcoats. When he does "dress down" though, he favors dope semi-casual looks like this killer bomber jacket pictured above.
Ryan Gosling
Notable Partners: Sandra Bullock, Famke Janssen, Rachel McAdams, Jaime Murray, Kat Dennings, Blake Lively, Casey LaBow, Olivia Wilde, Eva Mendes
He's your girl, mom, and sister's favorite actor for reasons not pertaining to (or at least, not limited to) his acting ability. His rep for quality actress pulls is matched only by his typical steez: dope knits, solid heritage clothing on his downtime and impeccably tailored suits when it's carpet time.
John Mayer
Notable Partners: Vanessa Carlton, Jennifer Love Hewitt, Jessica Simpson, Minka Kelly, Jennifer Aniston, Taylor Swift, Katy Perry
Probably the most infamous ladykiller on this list, Mayer loves bicken back in white-tee Brando steez or draping himself head to toe in Visvim almost as much as he loves wooing whichever pop singer or actress is holding the "It Girl" title. And by wooing we mean scooping them up for like a year at best then discarding them and starting over. Game just rewinds.
Sean Penn
Notable Partners: Elizabeth McGovern, Madonna, Jewel Kilcher, Robin Wright, Elle Macpherson, Petra Nemcova, Natalie Portman, Jessica White, Scarlett Johansson, Garcelle Beauvais, Charlize Theron
After ending his marriage of almost twenty years to the smoking hot Robin Wright (that's Claire Underwood to all you newbies) at the top of the decade, the acting vet has been playing the field with actresses almost 15 years his junior. Going from a still stunning Robin Wright to the likes of Scarlett Johansson and Charlize Theron is enough to boister anyone to give very few fucks, an attitude that's seeped into Sean's middle-fingers-to-the-rules steez. This guy showed up to a Cannes Film Festival event looking like he was headed to a ranch or, gallery party in Williamsburg or something and completely killed it. Mid-life flourish would be the more appropriate term, no?
George Clooney
Notable Partners: Kelly Preston, Talia Balsam, Elizabeth Daily, Kimberly Russell, Lucy Liu, Lisa Snowdown, Jennifer Siebel Newsom, Krista Allen, Sarah Larson, Elisabetta Canalis, Stacy Keibler, Amal Alamuddin
Normally we try and judge style on more than just suits because, when you're a Hollywood A-lister that's easy, but when said A-lister looks as good in a suit as George Clooney does (no pause necessary) that formality is waived. Sure, the silver fox gawd is pretty Normcore in the rare times that he's not super casual, but when he's busting Leo DiCaprio's ass on the basketball court and bagging up actresses half his age, does that even really matter?
Jack Nicholson
Notable Partners: Kelly LeBrock, Georgiana Carter, Mimi Manchu, Susan Anspach, Angelica Houston, Winnie Hollman, Rebecca Broussard, Julie Delpy, Lara Flynn Boyle, Kate Moss
What else is there to say about this king? He's a Hollywood OG who, in the downtime between a handful of iconic roles and posting up courtside at every Lakers game—usually in all-black-everything—has slayed half of old Hollywood, rarely ever settling down. His last two notable girlfriends were Lara Flynn Boyle and Kate Moss in the early aughts, i.e. his early 60s. Dude was pulling models even after he graduated from his casual wear youth to his cozy boy but still fresh old age. Swag Lord Extraordinaire.