Weather Vain: Charleston, South Carolina - 81 and Partly Cloudy

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The weather’s starting to turn in NYC, but in Charleston? Definitely still walking-down-King-Street-in-sandals temps. —erica

Clockwise from top left:

+ A minimalist Miranda Bennett that’ll earn appreciative nods from the guys at the cool-dude shop Indigo & Cotton.

+ A pair of simple slides from The Palatines—for shuffling around Heirloom Bookshop, prettiest cookbook store imaginable.

+ To keep the sun out of your eyes on the roof of The Vedue: this Rag & Bone visor.

+ A 10 Crosby Derek Lam skirt that’s WAY ready for an oyster-fueled meal at The Ordinary.

+ Alynne Lavigne earrings the color of High Wire’s sorghum whiskey.

+ A slick, silver clutch by Baggu that’s ready for any ol’ thing.

Click, click, click for more “Weather Vain.”

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Weather Vain: Seattle, Washington - 64 With a Chance of Rain

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The weather in Seattle today is very…Seattle-y. Here’s how to dress for it. —erica

Clockwise from top left:

+ Some freakin’ awesome Rachel Comey rain boots—so that the forecast doesn’t keep you from exploring Olympics Sculpture Park.

+ A Cook & Gates tote—in case you stumble upon something you can’t pass up at Totokaelo.

+ Skinny sweatpants from Rag & Bone that you should probably never travel without again.

+ An Apiece Apart sweater as minimalist and perfect as the decor at Bar Sajor.

+ What’ll put a smile on your face as fast as a scoop of melted chocolate ice cream from Molly Moon’s? This Bing Bang cuff.

+ A blue braided Aurelie Bidermann bracelet—to compensate if the sky’s gray all day long.

Whoa, so much more “Weather Vain” over here.

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In Character: Rachel Green

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Admit it: A lot of your nineties outfit inspo comes from teenagers, fictional or otherwise (see: Rayanne Graff, Drew Barrymore, Cher Horowitz, Fiona Apple). But if you’re looking for someone who really nails the I’m-trying-to-be-an-adult-ok? thing, Rachel Green’s your girl—especially during season one of Friends, which premiered 20 years ago this week (WHAT). —erica

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A 3.1 Phillip Lim sweater, for snuggling Ross and/or Marcel.

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One last dress—from Rag & Bone—charged to her dad’s credit card.

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A Band of Outsiders button-down that can cappuccino spills from waitressing at Central Perk.

There’s a whole lot more where this came from!

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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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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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