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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In Character: Puss in Boots

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Personalities deserving of their spinoffs: Lauren Conrad, Wolverine, Flavor Flav, and Puss in Boots. I mean, that cool cat obviously knows how to accessorize. —erica

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A Janessa Leone hat that can be clutched to sell that whole I’m-just-a-sweet-kitty act.

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An Isabel Marant belt, ready to hold a sword that’s almost as big as he is.

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Over-the-knee boots from Alexander Wang that Donkey’s likely jealous of.

More of this! Here!

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Couple Up: Claire Danes and Ben Lee

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Did you listen to Ben Lee’s music for the first time because he was Claire Danes’s BF? Didya? We get it. They were just so…so…late-nineties, minimalist, living-in-Soho cool. —erica

Claire Danes: Open-back Alexander Wang sandals, a sleeveless turtleneck sweater from Yigal Azrouel, and perfect stovepipe khaki pants by Jason Wu.

Ben Lee: Black Acne pants, a loud, floral Vito Rhody shirt, and beaten-up Golden Goose sneakers

More nostalgic pairings to be had!

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Next Level: Ankle Ties

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These shoes? Fit to be tied. Har, har—I know. But don’t you dare let my bad puns distract from just how good-looking these four pairs are. —erica

LEVEL I: Alexander Wang does black and sleek and Helen of Troy-worthy.

LEVEL II: How quickly would these House of Harlow sandals jazz up any of your summer dresses?

LEVEL III: Sophia Webster knows how to make any old LBD fit for a  black-tie situation.

LEVEL IV: These Charlotte Olympia suckers = SO HIGH. But with a cropped jean and a chambray shirt, they’d feel substantially more manageable.

All the “Next Level.” Right here.

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Where They Were Then: Alexander Wang

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This guy’s a textbook wunderkind. The dude who defined the model-off-duty look has been on the scene for less than a decade, and he’s made quite the name for himself. —bea koch

1984 - Born in San Fran to Taiwanese-American parents, Alexander is the youngest of three.

1986 - Two-year-old Alexander scribbles dresses and shoes on any scraps of paper he can find, and his mom rewards him with a sewing machine.

1993 - When his parents move to China, Alexander decides to stay in easy-breezy Cali and enrolls in boarding school.

1999 - At 15, he wants to get more serious about this whole design thing and takes summer classes at the venerable Central Saint Martins in London. That same year, he stages his first fashion show…at his brother’s wedding. Talk about a supportive fam!

2002 - Alexander moves from his beloved CA to NYC to attend Parsons. He snags internships at Marc Jacobs and Teen Vogue while he’s at it and sells shoes at Barneys to make some cash.

2005 - Betting on himself, Alexander drops out of Parsons to launch his own line. And his family’s behind him: His sister-in-law Aimie joins him, helping develop a collection of six knit pieces. After Diane von Furstenberg spots an employee rocking an Alexander Wang original, she offers the newbie a job—but he turns her down. No hard feelings: DVF’s still a total fangirl.

2006 - Alexander doesn’t have to search far for someone to style his debut collection: He taps high-school pal Vanessa Traina and credits her—and her mom, romance queen Danielle Steel—as a huge inspiration for his Cali-cool looks.

2008 - Welp, that was fast: Alexander wins the two biggest prizes for any up-and-comer, the Ecco Domani Fashion Foundation award and the CFDA/Vogue Fashion Fund one. Oh, and his line for Uniqlo, available at the company’s Tokyo store, sells out in 30 minutes flat!

2009 - Alexander diffuses big time—with footwear, eyewear, menswear, and most importantly, T by Alexander Wang, his more basic (slash affordable) line. Plus: He’s named the Swarovski Womenswear Designer of the Year.

2010 - After a few years of what seems like universal support, famed New York Times critic Cathy Horyn takes aim at Alexander with a pointed review that decries the “weightlessness” of his designs.

2011 - Named GQ’s Menswear Designer of the Year, Alexander takes that momentum and opens a store in Soho. It has a fox fur hammock.

2012 - Up-and-comer, what? Guess who’s the new creative director at the very-big-deal house of Balenciaga? But the good news is tempered by the bad: Several former employees file a $450 million lawsuit against Wang, alleging unsafe working conditions in his Chinatown factory. A settlement is reached, and the suit’s dismissed—but not before tarnishing Alexander’s once-flawless rep a little.

2013 - Alexander’s debut for Balenciaga pays tribute to the storied history of the brand—but also delivers that signature A. Wang cool. The line is a hit with starlets like Carey Mulligan, who shows up in architectural pieces from the collection at the Met Ball and Cannes. Oh, Mr. Wang’s namesake line gets a shout-out in Justin Timberlake’s “Suit & Tie.”

2014 - Courting controversy, Alexander invites the fashionable world to view his fall 2014 collection in *gasp* Brooklyn. Not shocking: It’s totally worth the black-car ride across the East River. And word is an H&M collab is coming in Nov…

Read on—stories of more of your faves right this way.

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Next Level: Pleated Leather

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There’s nothing wrong with a classic motorcycle jacket, but I’m way into the idea of leather standing in for cotton, wool, or satin—fabrics with some real movement. Throw some pleats into the mix? Oof, I’m done. —erica

LEVEL I: On this Alexander Wang dress, the leather’s an accent—a very, very killer accent.

LEVEL II: I’d like to think I’d still wear this BLK DNM skirt when I turn 60.

LEVEL III: From Derek Lam, this sucker's very Clueless in an Amber-goes-to-gym-class way.

LEVEL IV: It might not freshen your breath, but, DANG is this Alice + Olivia skirt minty.

More “Next Level!” Go here!

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Of a Kind

Q: Are football tees the new baseball tees? Alexander Wang thinks so. —erica

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Weather Vain: Memphis, Tennessee - 54 and Partly Cloudy

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Beale Street, Graceland, and some lovely weather—here’s how to take full advantage of Memphis on a rockin’ day like this one. —erica

Clockwise from top left:

+ The ideal in-between weather trench from Jenni Kayne.

+ An Alexander Wang bag in a blushy pink that would fit right in at The Peabody Hotel

+ Notify jeans that would be totally unaffected by BBQ stains.

+ Earrings, by Cold Picnic, that are chill enough for a late night at The Cove (with a whole bunch of oysters).

+ For a meandering stroll through Midtown: a pair of Thierry Lasry sunglasses.

+ Pour La Victoire wedges sturdy enough for some after-dinner bocce at Hog & Hominy.

+ The kind of Base Range tee you can-slash-should wear anywhere, any day of the week.

More outfit ideas (and travel tips) right here.

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Couple Up: Gwyneth Paltrow and Brad Pitt

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Years before Team Aniston and Team Jolie were a thing—such a thing!—it was all about Gwyneth and Brad, with their matching jeans, matching sunglasses, and (eventually) matching haircuts. Here’s how they rolled. —erica

Gwyneth Paltrow: A basic white tee from Everlane, a Band of Outsiders leather blazer, and some mom jeans c/o Denim Refinery.

Brad Pitt: A Krochet Kids beanie, a worn-in sweater by Alexander Wang, and a pair of light-wash Simon Spurr jeans.

For more couples we miss, click this way.

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Couple Up: Evan Rachel Wood and Marilyn Manson

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Remember how CRAY it was when Evan Rachel Wood started dating Marilyn Manson? She was 19, and he was 36. She was the girl from Practical Magic and Thirteen, and he was known for his onstage, er, antics. But we’ll give them this: They were together for four whole years, which is like two decades in Hollywood time. Here’s how we’ll always remember them. —erica

Evan Rachel Wood: An oversize tux jacket by Alexander Wang, a red pleated Tibi skirt, and Jeffrey Campbell mary janes.

Marilyn Manson: A hardware-less Alexander Wang moto jacket, a Markus Lupfer skull tee, and AJ Morgan tortoise aviators.

Reminisce about more one-time twosomes here.

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