Hotter with Hats?

Do Ashton and other guys look cuter in caps? Get the scoop from hatmaker Eugenia Kim – then cast your vote and see results in our Sexiest Man Alive special issue, on newsstands Nov. 18. By Emily Fromm

01 of 10

ASHTON KUTCHER

ASHTON KUTCHER
PATRICK RIDEAUX/REX; Michael Simon/startraks

Kutcher's headgear of choice? The trendy trucker cap. "He doesn't take so much care of his hair, so this is definitely a good look to just throw on," says New York City-based hat designer Eugenia Kim, who recently launched a men's line (her fans include Usher and Johnny Depp).

02 of 10

JOHNNY DEPP

JOHNNY DEPP
ALEC MICHAEL/GLOBE; Joe Takano/Orion Press/ABACA

Depp likes to top off his style with a little whimsy. "He knows how to wear a hat right, so that it flips up on one side and is very flattering with his cheekbones," says Kim. Plus, "he has such an innocent look, and the fedora's a hat that gives a little bit of attitude."

03 of 10

ENRIQUE IGLESIAS

ENRIQUE IGLESIAS
Teresa Astudillo/ The Grosby Group/Ramey; JOHN ZISSEL/IPOL/GLOBE

The baby-faced singer may be trying to toughen up his image with a military-style cap, but Kim says his efforts backfired: "He almost looks prettier with it on!" (Her suggestion: "If it were slightly more boxy, I think it would work better with his jawline.")

04 of 10

GUY RITCHIE

GUY RITCHIE
Fame; Ian West/PA/AP

Like his wife, Madonna, Ritchie has an affinity for the old-fashioned newsboy cap. "He looks really young with the hat on, like a little Oliver Twist," says Kim. "He looks so English – but he looks cute either way."

05 of 10

TAYE DIGGS

TAYE DIGGS
Glenn Weiner/STargaze; Dan Herrick-KPA/ZUMA

Diggs's dapper homburg-style hat "is a huge thing in hip-hop," says Kim. "He looks more street, he looks like he has more attitude – but the hat could really work for him if it slipped down on one side a little bit more."

06 of 10

KEVIN FEDERLINE

KEVIN FEDERLINE
Jeffrey Mayer/Starfile; Splash News

He may be from Fresno, Calif., but Mr. Britney Spears shows his New York City pride in a Yankees cap that appears to be brand new. "He just bought that hat and put it on," says Kim of Federline's flat-brimmed topper. "It's not worn in."

07 of 10

KENNY CHESNEY

KENNY CHESNEY
Don Heupel/AP; Mark J. Terrill/AP

Chesney's chapeau does more than hide his shiny pate. "The cowboy hat is like a facelift, because you have the brim coming from the sides up, so that naturally lifts up your face," says Kim. "Plus it shades just the right points – it's like eye shadow for men."

08 of 10

WILMER VALDERRAMA

WILMER VALDERRAMA
Amanda Edwards/Getty; Albert L. Ortega/startraks

"He really looks like a thug," says Kim of the That '70s Show actor's appearance in a tight-fitting skullcap. Except for one thing: "He has a round face, and the hat is accentuating the top, round part of his head, so his face looks a little chubby."

09 of 10

50 CENT

50 CENT
Getty Images; Dan Herrick-KPA/ZUMA

"I think the doo-rag works for him," says Kim of the rapper's scarf-cap combo. "The beauty of caps in general is you have to make them work for your individual style." Also winning Fitty points? "He's wearing his hat asymmetrically, which is very flattering."

10 of 10

BEN AFFLECK

BEN AFFLECK
X17; Jim McIsaac/Getty

The die-hard Boston Red Sox fan supports his favorite team on his hat (among other garments). "He looks a little more comfortable with the cap – it's sort of his post-frat-boy look," says Kim. "But he has really good hair, so he could go with or without."

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