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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Of a Kind

Ok, brilliant: trompe l’oeil saddle shoes from Band of Outsiders. —erica

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In Character: Nina Sergeevna

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Question 1: Are you guys watching The Americans? Question 2: If not, why? Nina Sergeevna—an employee at the Soviet embassy played by the sultry-as-what Annet Mahendru—is one of those supporting characters that sucks you right in. And her wardrobe’s pretty baller, too. —erica

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A Band of Outsiders shirtdress down to woo an FBI agent.

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A serious, shrunken blazer from The Row that belies that underwear collection of hers.

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Ursa Major earrings that take a strange turn—just like her story (BOOM).

If you’re looking for an “In Character” fix, here’s your chance.

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Next Level: Long-ish Shorts

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Who wears short shorts? Not everyone. And if you’re looking to keep your upper thighs to yourself, here are four ways to do so. —erica

LEVEL I: Denim cut-offs—but in a totally unexpected way, thanks to Vladimir Karaleev

LEVEL II: These cotton Band of Outsiders suckers almost look like board shorts—and would be killer with a stacked sandal.

LEVEL III: Um, laser-cut polka-dots—that’s the 3.1 Phillip Lim way.

LEVEL IV: So loose and girly at once! How about these Steven Alan guys with a just-cropped top and a straw hat?

More “Next Level!” Come and get it.

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In Character: Billy Madison

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Graduation season is upon us. And if this was 1995, we’d all be patting Billy Madison on the back for passing 12th grade (well, all the grades, really). Below, how to cop his back-to-school look. And if this isn’t enough for you, check out this tribute from Four Pins—it’s for real. —erica

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A Marweather hat that rules. Just like O’Doyle.

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A preppy-as-they-come Band of Outsiders sweater—with the sleeves ripped off, for better golf-carting.

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A baseball jersey, from Opening Ceremony, that the hot third-grade teachers gotta respect.

Whoa, so many more “In Characters.” Have at ‘em.

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In Character: Janis Ian

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Mean Girls is 10 years old. The internet has probably already told you that. And though we paid tribute to the Plastics back in the day, we thought it was about time to give a shout-out to Lizzy Caplan in her very wonderfully acerbic—Spring Fling Queen-nominated!—role. —erica

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A Band of Outsiders bow tie that attracts the Mathletes.

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A Denim Refinery vest that would probably get a mention in the Burn Book.

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A seriously tough K/LLER ring made of metal, not cold, hard, shiny PLASTIC.

Big into “In Character?” Head here.

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Next Level: Palm Prints

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Here in NYC, we don’t have palm trees in our yards, but we can have them on our bodies (or in our smaller-than-they-should-be apartments). Leaf it to these four to deliver a dose of the tropics. —erica

LEVEL I: A Katie Kime tray—for your jewelry or for all of the change you’re saving to plan a getaway.

LEVEL II: Who says there’s gotta be green? Not Kenzo.

LEVEL III: Band of Outsiders takes the ultra-cozy approach: a potted palm sweater that looks really ready to curl up with a paperback.

LEVEL IV: MSGM isn’t afraid of an out-there color combo, and you shouldn’t be either.

Get a whooooole lot more “Next Level”

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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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