x023 HQs Opening of Sephora at 5 Times Square

x011 Leighton and Sebastian attend Katy Perry concert

x011 Leighton and Sebastian attend Katy Perry concert

x043 MySpace presents Taylor Momsen’s 16th Birthday

x011 Teen Vogue (Cover)

x104 07-27-2009: Filming Season 3

x006 Men’s Health Photoshoot

more x004 Jonathan Skow Photoshoot

x047 07-24-2009: Filming Season 3

x031 July 4th BBQ at The EMM Group Estate

x024 Gossip Girl Icons

x175 07-06-2009: Filming Season 3

x006 Complete Woman Photoshoot

x007 Taylor outside her NYC Hotel

In our annual salute to the clothes that will help you weather the brisk months ahead, actor Ed Westwick reaches for the pieces that embrace timeless style and construction. Because the best gear shouldn’t last just one season but a lifetime.

*****

On the first-ever episode of the outrageously hyped television sensation Gossip Girl, Ed Westwick’s character, Chuck Bass, bookended a pair of date-rape scenes with a weed reference and the memorable zinger—delivered to the show’s principal, Serena—“Your life is over, slut!”

“Villain is such a harsh word,” Westwick says from a hotel room in Washington, D.C., where he has just attended the White House Correspondents’ Dinner. It’s hard to imagine what a recently minted 22-year-old television antagonist from England was doing pressing the flesh with Beltway muckrackers. But Westwick, who looks like Jude Law crossed with a pre-psychotropic-meltdown Joaquin Phoenix, assures us in his assured British way that “everyone who is anyone was there.”

If that makes Westwick sound like a bit of a dick, surrender now—it’s part of his appeal. Just ask Gossip Girl’s freakishly wide-ranging demographic of religious watchers, many of whom are as entertained by the incestuous nature of the cast as by the show itself. Westwick dates co-star Jessica Szohr (they played kissy face at our shoot) and is roommates (cute!) with Chace Crawford. When pushed to dish, Westwick minimizes the thin line between work and play, and fair enough. You’d date a co-worker if she looked like Jessica Szohr.

In our annual salute to the clothes that will help you weather the brisk months ahead, actor Ed Westwick reaches for the pieces that embrace timeless style and construction. Because the best gear shouldn’t last just one season but a lifetime.

Still, is there a downside to all that Gossip glare? What happens when TV’s latest prep-school bad boy tours Arlington Cemetery with his real-life parents? “Every time the tram would stop, these girls would come up, giggle, then run off,” Westwick says. “You feel like the kid in school that everyone’s laughing at.”—will welch

x019 HQs Penn strolls down the street while chatting on his cell phone

x014 HQs Jessica and Ed hang at Bardot Nightclub with friends

x047 HQs Jessica and Ed out and about in LA

more x018 2.24 Valley Girls

more x014 HQs 2.25 The Goodbye Gossip Girl

x003 HQs Penn, Blake, Alexis and Amber have dinner at Five Points

x033 Hollywood Life’s 11th Annual Young Hollywood Awards

x023 Omega Celebrates 40th Anniversary Of The Moon Landing

x011 The Ultimate Prom 2009

x008 Venice Magazine

x018 Glamour Women of the Year Awards 2009

x008 8th Annual Chrysalis Butterfly Ball

x029 W Hotel Grand Opening

x063 HQs MTV Movie Awards

x006 HQs Ed and Jessica spotted together enjoying the day off

x007 Stewart Shining Photoshoot

x001 Jennifer Rocholl Photoshoot

x033 Burberry Americas Headquarters Lights Up New York Skyline

x038 Z100’s Zootopia 2009 at the Izod Center

x028 “Terminator Salvation” Los Angeles Premiere

x014 2.25 The Goodbye Gossip Girl

x014 LA Galaxy Celebrity Soccer Match

x022 Kenneth Cappello Photoshoot

x020 Leighton filming “The Roommate”

x007 Celebrity Sightings In Los Angeles

x006 Celebrity Sightings in Los Angeles

x033 HQs “Star Trek” Los Angeles Premiere