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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Of a Kind

A printed dress and jacket combo typically feels so…bridal luncheon. But not with the help of Veda and some LEATHER. —erica

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Couple Up: Cindy Crawford and Richard Gere

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Most photos of Cindy Crawford and Richard Gere involve her wearing a cut-down-to-there dress and him done up in suit. (Oh, and there’s also this Herb Ritts shoot for Vogue in 1992.) Turns out, these two did go places together that didn’t involve a red carpet, though, and when they did, it was kind of hilarious, outfit-wise. —erica

Cindy Crawford: A cross necklace by Alexis Bittar, a floral Minkpink skirt, and the perfect denim jacket from Current/Elliott.

Richard Gere: A loud Huf hat, a sweatshirt (thrown over the shoulders) by Todd Snyder for Champion, and dark-as-they-come Super sunglasses.

Lookin’ for more throwbacks? You’re in luck.

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Weather Vain: Washington, D.C. - 70 and Clear

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Go for the cherry blossoms, stay for the weather? Here’s how to make the most of a day in the District. —erica

+ An Organic by John Patrick shirt just serious enough for a business lunch at RIS.

+ This Ariel Gordon ring—totally jibes with the color scheme at Rasika West End.

+ A Vanessa Bruno jacket that Olivia Pope would be very into.

+ Annie Costello Brown earrings, delivering a dash of edge.

+ A Collina Strada pouch with leather that matches Dolcezza's strawberry-tarragon gelato. MMMMM.

+ Flats from Tibi—for doing some time at the Newseum.

+ The sort of L’Agence pencil skirt that would fit it at the Park Hyatt's bar.

For SO much more “Weather Vain,” click here.

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