Couple Up: Gwyneth Paltrow and Brad Pitt

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Years before Team Aniston and Team Jolie were a thing—such a thing!—it was all about Gwyneth and Brad, with their matching jeans, matching sunglasses, and (eventually) matching haircuts. Here’s how they rolled. —erica

Gwyneth Paltrow: A basic white tee from Everlane, a Band of Outsiders leather blazer, and some mom jeans c/o Denim Refinery.

Brad Pitt: A Krochet Kids beanie, a worn-in sweater by Alexander Wang, and a pair of light-wash Simon Spurr jeans.

For more couples we miss, click this way.

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Of a Kind

Come ON with this cuteness, Band of Outsiders! —erica

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Weather Vain: Pittsburgh, Pennsylvania - 25 and Partly Cloudy

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WELCOME TO WINTER, Y’ALL. Here’s how to survive embrace it in the City of Champions today. —erica

Clockwise from top left:

+ A steel-colored MHL by Margaret Howell sweater. Cause, you know, Steel City.

+ Mittens from Saturday focused on keeping your paws as toasty as possible.

+ A Sophie Hulme purse that makes up for the lack of foliage at The Point.

+ The sort of Band of Outsiders coat you won’t take off ‘til the Penguins wrap up their season.

+ This Eugenia Kim headband = as cozy as the short rib flatbread at Meat & Potatoes

+ Mociun earrings—chill enough for a few beers c/o The Brew Gentlemen.

+ Maison Scotch cords that make it easy to try on clothes at the shops on Indigo Square.

+ Warby Parker glasses, to pore over the massive selection of second-hand scores at Book Tree.

More “Weather Vain!” Go!

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Next Level: Dressy Jumpsuits

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Is there a reason—a good one—that a jumpsuit can’t get a little serious, a tad grown-up? Don’t think so. These are four that mean it. —erica

LEVEL I: Steven Alan goes super-classic. You know, for a jumpsuit.

LEVEL II: Huh! This A.L.C. getup looks like separates without the trouble of putting an outfit together.

LEVEL III: Yah, yah, strapless. But put a blazer over this 10 Crosby guy—a tuxedo jacket, even?—and it’s ready for action.

LEVEL IV: Get a load of those pinstripes and pleats, via Band of Outsiders. This sucker is very Serious Business Lady in a Melanie Griffith way.

Fall down the “Next Level” rabbit hole.

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In Character: Tina Carlyle

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Even more memorable than that savvy dog Milo was Cameron Diaz’s breakout role in The Mask, which came out a full four years before There’s Something About Mary (and, um, nearly 20 years ago now). Here, three dresses that epitomize her look—best described as SMOKIN’. —erica

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A vampy little Rachel Pally situation that can help a girl gather all sorts of intel at the Edge City Bank.

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The type of Band of Outsiders dress that compels men to swallow bombs to save you.

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A sequin number from Haute Hippie—ready to attract some major attention at the Congo Bongo.

Want more “In Character?” You got it.

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Next Level: Embroidered Pants

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Ready to put on some fancy pants? Oh, GOOD. ‘Cause we have just the pairs for you. —erica

LEVEL I: The gray stitching and abstract motif on these guys is so subtle-cool—which is basically Isabel Marant's M.O.

LEVEL II: These Band of Outsiders pants say, “I have really dope parties at my summer house in Newport.”

LEVEL III: Though these 3.1 Phillip Lim puppies can totally go dressy, how good would they be with a half-tucked white tee?

LEVEL IV: Mara Hoffman is not afraid to go there. Clearly.

Ready for a lot more “Next Level” action? It’s a click away.

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In Character: Clark Griswold

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AHHH, summer vacation. It’s upon us. And if you don’t have any big holiday-weekend plans, maybe you want to cozy up on the couch and make like Rusty, sharing a six-pack with the ultimate road-trippin’ dad? Here, how to rip off his look. —erica

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A Barque polo that says, “My wife picked this out for me.”

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A Band of Outsiders khaki bomber—cool enough to attract the attention of the blonde in the Ferrari, maybe?

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YMC x Clarks loafers as classic as a trip to Wally World.

Another good Saturday activity: a deep dive into the “In Character” archives.

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