From Kurt to Bowie, The Most Stylish Dudes and Why We Ladies Love ‘Em

It's far too often that fashion gets deemed as a women's-only sport, but there are few things sexier than a well-dressed man. From fitted shirts to perfectly worn-in jeans, a dapper dude has serious power over his duller counterparts. To pay homage to our beloved beaus of the ball, we've put together the most stylish guys from whom we continuously glean inspiration. So send your shirts to the tailor and ditch those carpenter jeans—take a cue from these who have made sartorial history.
Bob Dylan
Trot through any San Franciscan 'hood and you'll find a Dylan doppelganger at every turn. The look is iconic now, but the finger-in-light-socket hair (perhaps Dylan spent too much time "Blowing In The Wind"?), Ray-Bans, and beatnik duds changed an era.
Above, from left: Traveler Sunset; Fanpix.
James Dean
With a perfectly disheveled coif, rugged outerwear, and his accessory of choice dangling out the side of his mouth, James Dean was everything that a sensible, responsible, young person is not.
Kurt Cobain
One of the most stylish things about any man is when he doesn't try too hard. Kurt's so-cool-it-hurts swagger defined the '90s and gave us all leeway to wear our father's old flannels out of the house.
Above, from left: Burnout; Starpulse.
Louis XIV
There are few men in history who have successfully pulled off a man-heel, but there are fewer who have done it wearing tights, pastel waistcoats, and a wig. Those willowy "ballet legs" didn't hurt his steez either.
Jimi Hendrix
It seems like hordes of Wasson-philes have copped Jimi's great military jackets, bedazzled denim, and shredded flares, but the guitarist rocked them first and did them best.
Above, from left: Rolling Stone; Rolling Stone.
David Bowie
The master of androgyny and the king of facepaint, David Bowie's chameleon style has served him well from his red-hot mullet days to his current stark suits. Also, no one pulls off the eye-patch quite as well as the Thin White Duke.
Above, from left: Answers; 63antic'sblog.
Jean-Michel Basquiat
With painting as eclectic and intricate as his artwork, it's no wonder that Jean-Michel Basquiat also had great style. Delightfully kooky and always off-center, the guy's wardrobe ran the gamut from quirky to enchantingly bizarre.
Above, from left: Panache Report; Cult Case.
Yves Saint-Laurent
Thick glasses, a dapper side-part, and skinny bespoke suiting made Yves Saint-Laurent a style star at a young age, but his take on haute couture was what made YSL a household name.
Above, from left: Indiwo; V Buzz Blog.
The Ramones
Joey, Johnny, Tommy, and bassist Dee Dee's downtown look turned Robin-Hood hair into something to be desired. Striped tops, painted-on denim, and teeny leather jackets ruled CBGBs, and if you look up and down the Bowery today, you'll still see their influence.
Kanye West
From "internships" at Louis Vuitton to completing Fashion Week circuits like a seasoned editor, Kanye West did his best to bring color back into the fashion palette. "Dressed smart like a London bloke," Kanye's making menswear hip again.
Above, from left: GQ UK; Starpulse. Above, from left: The Advocate; Fashion Indie.

More from Politics

R29 Original Series