In Character: Van Wilder

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Ok, no, this is not a GOOD movie—and not just because Tara Reid is the most serious thing going here. But if you’re looking for a rainy-day excuse to spend a few hours with your couch and Ryan Reynolds? Well, it’s as good as anything going. Also: College-boy dressing in 2002—something to behold. —erica

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A Zanerobe shirt that eventually gets him lei’d.

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An Alexander McQueen chain wallet that makes the frat brothers of DIK especially nervous.

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A Saturdays hat, worn backwards to convince Taj to go for Naomi (“That’s ‘I moan’ backwards.”). 

More, more, more “In Character!”

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In Character: Clarissa Darling

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You know what Clarissa probably couldn’t explain? Her personal style. I mean, she was pretty much willing to try anything, and she wasn’t even remotely interested in coordinating—that matching business for Fergface (ew). —erica

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A Venessa Arizaga bracelet with some ‘tude—possibly a gift from Sam?

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An Alice + Olivia vest—because this one would never pass up a layering opportunity.

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Knit biker shorts by ALL Knitwear, to be worn under something plaid or floral or just plain crazy.

If you’re itching for more “In Character,” have at it.

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In Character: Daniel Desario

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In 1999, Judd Apatow and Paul Feig gave us James Franco. No matter how you feel about that 15 years later, you’ve gotta admit that dude was pretty stellar on Freaks and Geeks. He was the king of the burnouts and best bud to Nick Andopolis—a character played by Jason Segel, who, BY THE WAY, also made his debut on this show. Bam. —erica

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Wearing this Lynn & Lawrence hat means not having to shower. Right?

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A Rag & Bone henley in an earthy neutral—freak wardrobe essential at McKinley High School.

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A rumpled Carven shirt that Kim Kelly would totally borrow-slash-steal.

Get more o’ this business. A whole lot more.

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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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In Character: Shawn Hunter

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Ok, gang: The Boy Meets World spinoff premieres in July. Are you ready? Do you know how to find the Disney Channel on your teevee? While you figure all that out, let’s revisit the original and Shawn’s just-bad-boy, TGIF-approp look. —erica

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A Scotch & Soda leather jacket that really sells the rebellious-best-friend thing.

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A Kris Van Assche necklace Mr. Feeny probably thinks is silly.

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A Shipley & Halmos flannel that, along with that hair, draws in all the girls at John Adams High.

This way to the “In Character” archives…

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In Character: A.C. Slater

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This guy’s not afraid of color, pattern, or an all-in dance move. Let’s give it up for Albert Clifford. Oh, and, while we’re here: Go Bayside! Beat Valley! —erica

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A Gitman Bros. shirt way too cool for Preppy.

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Saturdays swim trunks that would make a splash at Malibu Sands.

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A T by Alexander Wang tank—to put the effects of wresting and football practice on display.

If you’re looking for more “In Character,” you’ve come to the right place.

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In Character: Taylor Vaughan

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No offense to Regina George, but I’m pretty sure that Taylor Vaughan was the best high-school movie villainess there ever was. (I mean, let that GIF up there remind you of her greatness.) Here, a tribute to the finger-wagging HBIC who was out to prove Rachel Leigh Cook Laney Boggs was not, in fact, all that. —erica

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A Tibi top to show off her spring-break-in-Florida tan.

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A skimpy pink bikini, by Minimale Animale, that caught the attention of Brock Hudson.

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A Milly gown ready to make a scene at prom (and to dance to Fatboy Slim, duh).

All the “In Character” you can take!

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In Character: Billy Madison

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Graduation season is upon us. And if this was 1995, we’d all be patting Billy Madison on the back for passing 12th grade (well, all the grades, really). Below, how to cop his back-to-school look. And if this isn’t enough for you, check out this tribute from Four Pins—it’s for real. —erica

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A Marweather hat that rules. Just like O’Doyle.

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A preppy-as-they-come Band of Outsiders sweater—with the sleeves ripped off, for better golf-carting.

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A baseball jersey, from Opening Ceremony, that the hot third-grade teachers gotta respect.

Whoa, so many more “In Characters.” Have at ‘em.

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In Character: Danny Castellano

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If you watch The Mindy Project, you have a thing for Dr. Danny Castellano. And if you don’t, what are you doing?! Here, an ode to a guy who gets us excited about gynecology. —erica

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Warby Parker glasses for jobs that require serious attention to detail, like decorating gingerbread houses, for example.

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A suede Billy Reid bomber that Mindy would definitely get cupcake frosting or spicy tuna on in a hot second—ya know, somehow.

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A pair of dancing loafers, from Carven.

But what would Mindy Lahiri wear? Oh, we got that, too.

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In Character: Janis Ian

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Mean Girls is 10 years old. The internet has probably already told you that. And though we paid tribute to the Plastics back in the day, we thought it was about time to give a shout-out to Lizzy Caplan in her very wonderfully acerbic—Spring Fling Queen-nominated!—role. —erica

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A Band of Outsiders bow tie that attracts the Mathletes.

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A Denim Refinery vest that would probably get a mention in the Burn Book.

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A seriously tough K/LLER ring made of metal, not cold, hard, shiny PLASTIC.

Big into “In Character?” Head here.

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