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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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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Couple Up: Anne Heche and Ellen DeGeneres

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Ok, LOOK at these two with their matching sunglasses. Is now the right time to say “I can’t even?” I hope so. —erica

Anne Heche: A wavy A Link necklace, a knit Gentryportofino dress, and a pair of AJ Morgan shades.

Ellen DeGeneres: A black silk shirt from Acne, a super-classic white Rag & Bone blazer, and (coordinating) Elizabeth and James sunglasses.

More cute (former) couples thisaway.

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Couple Up: Jack Nicholson and Anjelica Huston

On-again, off-again for nearly all of the seventies and eighties—so much dramz with these two. And so much good style. Can we get a primetime cable-TV movie about them? Please? —erica

Jack Nicholson: A Rag & Bone knit tie, a cotton-and-linen Billy Reid blazer, and Raen sunglasses.

Anjelica Huston: An easy-breezy Cook & Gates tote, a button-front Shaina Mote dress, and a simple K/LLER necklace.

Get into the “Couple Up” zone over here.

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Weather Vain: Providence, Rhode Island - 68 With a Chance of Rain

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Hey, now—don’t let the rain in R.I. get you down. Here’s how to keep things cheery (check out that bright white) in the Creative Capital. —erica

+ Native rain shoes that don’t actually look like rain shoes.

+ A VeraMeat necklace—simple but super-considered (not unlike the coolest hotel in town, The Dean?).

+ Rag & Bone white jeans, ready for a late-afternoon oyster-mushroom po’ boy at The Grange.

+ A sweater from Everly, in case you get chilly sitting in one of the 1492 seats at the Columbus Theater.

+ One of those linen tees, from 81 Hours, that you’d wear more than you wish to admit.

+ Mociun earrings that the kids at RISD would die over.

+ A Will Leather Goods wallet with a wristlet strap, to keep your hands free to clutch a White Electric Coffee mocha…and bagel.

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Next Level: Handkerchief Hems

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Festival season! Amirite?! Here’s how to add just a little hippie-dippiness to your look without going full-blown Vanessa Hudgens. —erica

LEVEL I: Oh, hey, office-approp! Thanks, Rag & Bone.

LEVEL II: Not as scary as it seems, this Elizabeth and James top: With a high-waisted skirt, you wouldn’t reveal midriff at all.

LEVEL III: Ah, yes, it’s a shapeless tent dress—but it’s a shapeless tent dress (from Wood Wood) that you’d live in, and you know it.

LEVEL IV: Opening Ceremony goes sunny. Just be careful around the subway grates. 

Looking for more ways to amp up your summer look? We have some ideas.

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Next Level: Leather Backpacks

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Backpacks have been, like, a thing for awhile now, but it seems like all of a sudden they are getting all leather-fied. These are four want to hang out with you and your shoulders. —erica

LEVEL I: Ahh, a Rag & Bone take that Felicity would have been totally into.

LEVEL II: Polished, right? That Phillip Lim knows what he’s doing.

LEVEL III: This Kara design's the size of one of those Prada backpacks you were desperado for back when, but that cross-hash design? It's actually mesh.

LEVEL IV: Just because it’s leather doesn’t mean it has to be fancy. Illesteva knows how to keep things chill.

Hey, any “Next Level” fans: Click here.

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Next Level: Chill Pencil Skirts

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Pencil skirts tend to feel so business-y—like the jumping-off point for a commercial from Mastercard (or, lately, Secret). Why so serious? Here, four ways to give the look a chill pill. —erica

LEVEL I: If you really want to go crazy, pair this Altuzarra take with a striped top.

LEVEL II: This Rag & Bone guy is a denim skirt for a grown-up (that’s you).

LEVEL III: The beat-up stitching motif on this 3.1 Phillip Lim sucker is way cooler than any of that weird distressing and whiskering that was once all the rage.

LEVEL IV: Spring colors, from Current/Elliott! Because how ready are you for bare legs?

Get your “Next Level” fix, here and now.

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Formal Statement: 20 Dope Prom Dresses (That Are All Under $300)

A little bird told us that it’s time to start shopping for a prom dress. Ok, no, that’s not entirely how it went down: A little bird (named Iryna) emailed us and asked, “Would you want to help a sister out and offer some prom dress/general evening dress suggestions?” Well, here you go, gurl: 20 ideas—all by super-cool designers and all less than $300—to get you started. And for those of you whose prom memories are currently being mined for #tbt fodder, I present this: a trip to the big-dance attire archives with Laney Boggs, Brenda Walsh, and Josie Grossie. —erica

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Left to right: Ryan Roche, Shona Joy, Erin Fetherston, Erin Fetherston.

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Left to right: Motel, J Brand, 10 Crosby Derek Lam.

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Left to right: Tucker, Horses Atelier, Alice + Olivia.

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Left to right: Alice + Olivia, Halston Heritage, 10 Crosby Derek Lam, Alice + Olivia.

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Left to right: Parker, L’Agence, Amanda Uprichard.

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Left to right: Halston Heritage, Acne, Rag & Bone.

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Weather Vain: Buenos Aires, Argentina - 80 and Mostly Cloudy

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Most of us north of the equator are probably itching to go south right now, and where better than B.A.? Here’s what we’d be working if we were jetting to the Argentine capital right now. —erica

Clockwise from top left:

+ An Alexa Sofia scarf nearly as sweet as Nucha's baked goods.

+ A Black Crane top, as chilled-out as the lofts at Home Hotel

Pants—from Base Range—baggy enough for a healthy portion of grass-fed beef at La Brigada.

+ An Elizabeth Knight necklace game for some Palermo Soho shoppin’ time.

+ Shades, by Warby Parker, for strolling Jardín Botánico Carlos Thays.

+ The sort of Rag & Bone vest you should always toss in a carry-on.

+ A made-in-Argentina bag from the talented ladies of Hare+Hart.

Loeffler Randall shoes that can handle a really, really late night.

Whoa, there’s more “Weather Vain!” Have at it.

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