Weather Vain: Chicago, Illinois - 44 With a Chance of Rain

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+ An Each x Other trench as white as the tablecloths at Pearl Tavern.

+ Ah, these Dieppa Restrepo loafers! The color of some GT Fish & Oyster king crab legs.

+ The perfect, easy-fitting black silk pants c/o Raquel Allegra.

+ A Carven shirt just crisp and business-y enough for the West Loop.

+ What do you know: a two-finger ring, from K/LLER, that’s actually a breeze to wear.

+ A Jenni Kayne blazer in Cubs colors—cause it’s officially that time of year, guys.

+ Shoulder bags—not great for layers. A backpack like this Jerome Dreyfuss one—a whole lot better.

+ This Orly Genger by Jaclyn Mayer bracelet = just weird enough for the out-there cocktails from Aviary

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Weather Vain: Santa Barbara, California - 71 and Partly Cloudy

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Now’s the time of year when we’re especially desperado to live in California—to have dependable weather that almost always qualifies as lovely. Here’s looking at you, Santa Barbara. —erica

Clockwise from top left:

+ An Ace & Jig top that you could totally throw on over a swimsuit when things heat up.

+ Perfect tortoise sunglasses—c/o The Row—to have on-hand at all times.

+ Boy by Band of Outsiders chinos—cuffed and ready to stroll throw the AVA Santa Barbara vineyards. 

+ A ring by A Peace Treaty that, with its triangle motif, pays tribute to the pizza slices (prosciutto and burrata, white anchovy and ricotta!) at Blue Tavern.

+ Walking shoes by Marais USA, down to hit Mission Historical Park.

+ An Acne jacket for when there’s a (sigh, perfect) chill in the air at night.

On the hunt for better weather? Start here.

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Couple Up: Emilio Estevez and Demi Moore

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Ok, tell me: Doesn’t throwback Demi Moore look like she could front a band playing Knitting Factory in Williamsburg? ANYWAY, get a load of the Brat Pack couple—they were engaged in the eighties, even. —erica

Emilio Estevez: Common Projects loafers, a perfect white T-shirt from Billy Reid, and Incotex gray pants.

Demi Moore: Slouchy pants from Otte, an Everlane cardigan, and Warby Parker glasses.

Double down on your “Couple Up” over here.

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Of a Kind

Babe, you are making me seriously want a pair of gray flannel pants. —erica

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Couple Up: Angelina Jolie and Billy Bob Thornton

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THESE TWO. There were the vials of blood they wore around their necks—ok, fact-checking says lockets with a drop of blood, but still—and all that public, er, heavy petting. A look back to Billy Bob’s marriage #5… —erica

Angelina Jolie: A thick Kule cuff, J Brand leather pants, and a Current/Elliott crewneck tee.

Billy Bob Thornton: A loud Robert Graham shirt, tan leather Built for Man pants, and Garrett Leight wire-rim shades.

It’s “Couple Up” central over here!

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Couple Up: Reese Witherspoon and Ryan Phillippe

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Did you know that Reese and Ryan met at her 21st birthday party? And she said "I think you’re my present?" Yah, true story. Here’s how it looked while it lasted… —erica

Reese Witherspoon: A mesh Breil Milano necklace, a slick little A.L.C. dress, and strappy sandals by B Brian Atwood.

Ryan Phillippe: A lavender Hickey Freeman shirt, slim black pants from Kai-aakmann, and wire-rim Original Penguin glasses.

More than a couple more couples—right here!

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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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Weather Vain: San Antonio, Texas - 55 and Overcast

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Oh, to be in Texas this time of year. Here’s how I’d wanna dress if I suddenly became a San Antonio girl today. —erica

Clockwise from top left:

+ A Pamela Love bracelet that’s like V-day just a smidge early.

+ A sweater that’s not afraid to go big, from 3.1 Phillip Lim.

+ A Reece Hudson wristlet, with enough cash shoved inside for a stop at Pearl Brewery Farmers’ Market.

+ Kicks—c/o Won Hundred—for bopping around Southtown.

+ A Bande des Quatres ring that would look damn good snuggled up with a glass of rioja at The Monterey.

+ Acne wool sweatpants—that leave plenty of room for queso.

Oh, we got some recs for Dallas, Houston, and Austin, too.

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Next Level: Black-and-White Daisies

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It can seem a little…aggressive to wear full-on, Technicolor florals during the grayest months of the year. But B&W ones? That’s something we can get behind—and Pollyanna would probably approve, too. —erica

LEVEL I: That sheer white fabric of this Lisa Perry dress is actually embroidered with daisies. Purty.

LEVEL II: It’s like a Kurt Cobain + Courtney Love wedding pic in a Minkpink shirt.

LEVEL III: Toss these Kenzo pants on with a gray sweater (or a blue one or an army green one…) and walk out the door.

LEVEL IV: What’s more nineties than daisy overalls (c/o Motel)? Tell me.

More o’ this goodness! Check it.

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Of a Kind

These Rodebjer pants = inspired by Phish-dancing girls of 1998. In the best of ways. —erica

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