Next Level: White Denim Jacket

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Know what’s easier to pull off than a pair of white jeans? One of these guys—they just feel so fresh, you know? —erica

LEVEL I: Basic in the best of ways, c/o Paige.

LEVEL II: Very “I’m cutting class at Laguna Beach High School,” this NSF number.

LEVEL III: Oof, sheeeek, Victoria Beckham. Do you think this jacket alone could prompt a Sabrina remake?

LEVEL IV: This Christian Wijnants take is somehow more relaxed AND more crisp than a classic blazer.

More pseudo-trends to try this way…

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Of a Kind

This oversize blazer by Objects Without Meaning is ideal for the star of an eighties rom-com. And that’s obviously intended to be a selling point. —erica

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Of a Kind

Move over, blue suede shoes. There’s a blue suede *jacket* (from Todd Snyder!) in town. —erica

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Couple Up: Madonna and Sean Penn

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Oof, were these two trouble. Their nickname was S&M, for chrissake, and during their time married in the mid-eighties, his rap sheet was possibly as long as his list of IMDB credits. I mean, they look like they’re up to no good, right? Course that was also their appeal. —erica

Madonna: A blacker-than-black Wendy Nichol bag, a lace-up shirt c/o The Kooples, and striped shorts from Thakoon Addition. 

Sean Penn: A slim Todd Snyder polo, a leather jacket by Nudie Jeans, and charcoal Rag & Bone pants.

Dip into the “Couple Up” archives.

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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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Of a Kind

Whaaaat is this jacket, Rosie Assoulin? Second question: It would make perfect sense to own the bag + hat too, right? —erica

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Of a Kind

Plaid is neutral, right? Obviously looking to validate owning this Dolores Haze moto jacket. —erica

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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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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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