In Character: Johnny “Drama” Chase

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What made Entourage so good? Ari Gold’s rants, Turtle’s girl issues, Mandy Moore’s Mandy Moore-ness, and Drama’s, well…everything about Drama, including his sense of style. We break it down below. —erica

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The sort of Notte shirt that can do +1 at a Cannes premiere.

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Aviators from Illesteva—to hide behind in the presence of Viking Quest super-fans.

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A form-fitting Olebar Brown shirt—hopefully it serves as a reminder to Vinnie to eat right.

More o’ this! Right over here!

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Weather Vain: Toronto, Canada - 72 and Clear

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The Toronto International Film Festival is underway! Here’s what to wear if you’re exploring the town SLASH watching movies all day. —erica

Clockwise from top left:

+ A surprisingly comfy By Malene Birger skirt—because elastic waistbands make theater seats a whole lot better.

+ Garrett Leight shades, so you get mistaken for a celebrity.

+ The sort of bracelet, by Giantlion, that you should pack for every trip.

+ A tote from The Stowe with plenty of room for chocolate-y snacks c/o Soma.

+ Loose and breezy—this Organic by John Patrick shirt is totally cool with you gorging on Campagnolo's wild mushroom pappardelle.

+ Rachel Comey mules that can handle a little shopping on Ossington Ave.

More of this “Weather Vain” thing! Lots more!

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Go Way Back: Aviator Glasses

With an uncanny ability to flatter just about anyone, aviators really deserve their spot in the classic-cool archives. Want to know how the shades became such a thing? Look no further. —maura brannigan

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The Origin: In 1936, the U.S. Army Air Corps commissions Ray-Ban to design sunglasses for its pilots entering World War II. The main goal: to protect from sun glare, which was known to cause headaches and altitude sickness. Oh, and the glasses need to look sharp, too. Though the design is produced especially for fighter pilots, it is available to the public just a year after its creation. 

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The Evolution: The aviator gets a whole lot more popular in 1941 when General Douglas MacArthur is photographed landing on a beach in the Philippines wearing his…and the image is splashed on the front page of newspapers nationwide.

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But the style doesn’t become hugely successful until the sixties, when rock-stars—like, oh, Paul McCartney and Ringo Starr—are snapped wearing them.

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The popularity falls off for a bit—blame it on John Lennon’s circular frames?—until Queen front-man Freddy Mercury wears ‘em in the album art for Mr. Bad Guy in 1985.

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One Tom Cruise singlehandedly cements aviators’ icon status with his starring role in Top Gun at 24.

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Controversial photog Terry Richardson, whose career really begins to heat up in the mid-nineties, is still rarely seen without his signature frames—a larger, boxier take on the originals.

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In 2000, an unknown actor named Johnny Knoxville creates a TV show called Jackass, which showcases people doing dumb stuff. It takes off (obviously), and Mr. Knoxville becomes a red-carpet staple—rarely seen without his go-to shades. 

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On the cover of Lenny—Lenny Kravitz’s 2001 album—his aviators make a prominent appearance, as does his earring collection.

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The Hangover absolutely destroys box offices during the summer of 2009—and its poster proudly displays not one by two pairs of the shades. Not at the table, Carlos! 

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Mary-Kate and Ashley Olsen do the rounds at New York Fashion Week in 2011 wearing trusty aviators (in a very non-fighter-pilot way).

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The Right Now: This summer, Warby Parker launches a range of super-hip aviators from the style minds of the Into the Gloss posse. Sheek.

Get a whole lot more “Go Way Back” action.

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Of a Kind

I shouldn’t like the crazy purple lenses of these Illesteva sunglasses. That’s what I keep trying to tell myself. —erica

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Weather Vain: Bozeman, Montana - 90 and Clear

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Not to get all Dixie Chicks on you or anything, but this time of year makes us yearn for wide-open spaces. Like, say, Montana, with all that National Park-ness…and lack of population density. Here’s how to embrace a day in Bozeman. —erica

+ A bangle from K/LLER that feels completely appropriate for a night at Plonk Wine Bar.

+ The ideal Ancient Greek sandals to slip on after hiking the M.

+ An Acne dress that’s plenty loose—in case you go hard at Granny’s Gourmet Donuts.

+ Cowboy poetry?! If you score some at Country Bookshelf, this AANDD bag has room.

+ Ahlem shades to take in all those Big Sky views.

More of this! Lots more! Here.

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Couple Up: Mandy Moore and Zach Braff

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When these two broke up, Mandy Moore wrote, oh, most of an album, Wild Horses, about him. Sample lyrics: “And I know you loved me in your way / I’m looking forward to looking back on these days.” Well, here’s to looking back, then? —erica

Mandy Moore: Tom Ford aviators, a cozy-looking Tess Giberson sweater, and a Rebecca Minkoff bag.

Zach Braff: Worn-in jeans from Ron Herman, a short-sleeve, just-dorky Steven Alan shirt, and a York St. by J. Press belt with a big, fat buckle.

Double down on your “Couple Up.” Right here.

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Couple Up: Lenny Kravitz and Lisa Bonet

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These two never met a pattern they didn’t like. I mean, to get inside their closets…oh, wait: That’s exactly what it’s like to be Zoe Kravitz, that beautiful creature. Damn her. —erica

Lenny Kravitz: A loud Yarnz scarf, a leather jacket from Billy Reid, and striped pants by Neil Barrett.

Lisa Bonet: A colorful Growing Jewelry necklace, a floral patchwork shirt from Markus Lupfer, and Saturdays sunglasses.

For more old favorites, head this way.

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Couple Up: Jared Leto and Cameron Diaz

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Wait, these two were really together for four years? How does that not seem possible to me? Tell me! Someone! So much time—and so many haircuts (some of them matching, even!). —erica

Jared Leto: A Cheap Monday ring, Baldwin camo pants, and a flowy white Apiece Apart shirt.

Cameron Diaz: A big Clare Vivier bag, slim J Brand black pants, and shades from Elizabeth and James.

Whoa, there’s a whole lot more “Couple Up” action to be had.

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In Character: Sloane Peterson

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Epitome of cool girlfriend, this one. And you know what else? She was working a man repeller look long before we even had a name for that—like, a whole 25 years before. Here’s a Sloane get-up appropriate for a day skippin’ school with Ferris and Cameron. —erica 

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Classic-as-they-come Alexander Wang x Linda Farrow sunglasses that look best in a 1961 Ferrari convertible.

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A white leather jacket by Acne that looks just right exploring the Art Institute.

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Long, loose 3.1 Phillip Lim shorts that would fly with Mr. Rooney’s dress-code policy, no prob.

Get more of this action right over here.

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Couple Up: Andre Agassi and Brooke Shields

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Andre and Brooke were a total curveball—ok, that’s the wrong sport, but you know what I mean. People is better at this than I am: When the two divorced in 1999, the mag titled its story “Double Fault.” Ah, there it is. Here, a look back. —erica

Andre Agassi: Silver hoops from Simon Sebbag, a T by Alexander Wang windbreaker, and a sweat-proof Huf hat.

Brooke Shields: Way-classic Super sunglasses, a polished Blk Dnm blazer, and coordinating silver hoops by Alexis Bittar.

More couples who once were!

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