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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Couple Up: Paul Rudd and Jennifer Aniston

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Paul Rudd and Jennifer Aniston have been a couple in two movies, The Object of My Affection and Wanderlust. But, turns they did stint together in real life, too, waaay back in 1998—and I’m pretty into the idea of them as a twosome. Maybe they broke up because of the soul patch he had for part of their relationship? —erica

Paul Rudd: A Pierrepont Hicks tie, a brown Everlane shirt, and a corduroy jacket from Billy Reid.

Jennifer Aniston: A Carven shrug (yes, shrug), a strapless column dress from Cedric Charlier, and a sparkly necklace by Tom Binns.

Get all the “Couple Up” you can handle if you head this way.

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Next Level: Contrast Collars

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Gordon Gekko loved himself a contrast collar, but that doesn’t mean you can’t, too. These four would look nice far removed from NYSE. —erica

LEVEL I: Jonathan Simkhai keeps things classic—and B&W.

LEVEL II: This Carven number is like a very girly play on the basic banker shirt. (Not that pinks only for ladies or anything, okay?)

LEVEL III: Oh, heeeey, chambray! The short sleeves of this Sacai guy keep it laid-back.

LEVEL IV: Why not go for a crazy print with that navy collar? Equipment's game.

Come check out the “Next Level” archives now.

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Weather Vain: Anchorage, Alaska - 34 and Clear

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I’m going to save my first adventure to the City of Lights and Flowers for a time of year when there are, you know, flowers, but if you happen to be in AK today, here’s what I think you should wear—and what you should do! —erica

Clockwise from top left:

+ A Carven turtleneck, for cozying up to some seafood at Marx Bros. Cafe.

+ Frame Denim jeans that aren’t too fancy for some reindeer sausage.

+ Floral Kenzo gloves—because it’s too frosty to really experience any of the stunning natural scenery.

+ A Baggu bucket bag as caramel-y as a Bavarian Hefeweizen from Glacier Brewhouse.

+ An Isabel Marant coat, with a hood! In case your ears get chilly.

+ A K/LLER bracelet that would look fiiiiine resting on the bar at Hotel Captain Cook.

+ Velvet slip-ons c/o Rag & Bone that are cozy enough to watch the Alaska Aces play some ice hockey.

There’s a whole lot of “Weather Vain” to be had if you’re looking…

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In Character: Enid Coleslaw

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We don’t get nearly as much angsty-teen-girl in our movies as we’d like. There’s Kat Stratford in 10 Things I Hate About You and Veronica Sawyer in Heathers, but Ghost World? That one doubles down. Meet the more misanthropic half, played by a so-good, where-is-she-now Thora Birch. —erica

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A leather jacket from The Sway that’s obviously a 1977 original punk-rock look.

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An Alice + Olivia shirt, for an inaugural visit to the creepy adult bookstore with Seymour.

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A green-and-black Carven skirt ready to move along to "Jaan Pehechan Ho."

Go “In Character” crazy over here.

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Weather Vain: Southold, New York - 46 and Partly Cloudy

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Y’all: Fall foliage season is wrapping up. Here’s how to make the most of the end if you’re hangin’ on Long Island’s North Fork. —erica

+ A Wool and the Gang knit hat that matches a glass of Croteaux Vineyards merlot.

+ FAUX/real's take on a pearl necklace—which is a lot cooler than an ultra-classic, East Hampton-worthy strand.

+ A sweater as cozy as a bowl of chowder from A Lure—c/o Carven.

+ Current/Elliott chinos that make East Coast prep look pretty freakin’ cool.

+ Marais USA boots as dark as the night sky as seen through at Custer Observatory telescope.

+ An Eddie Borgo bracelet as stunningly sleek as the squash for grabs at The Farm.

+ A Sophie Hulme clutch fancy-schmance enough to overnight at North Fork Table & Inn.

+ For strolling around Goldsmith’s Inlet Park: a snuggly wool coat from Surface to Air.

So much more “Weather Vain!” Get it.

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Of a Kind

Zebra stripes have never looked so subtle. Way to go, Carven. —erica

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Next Level: Wool Coats of Many Colors

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It doesn’t really get more sophisticated than a camel coat. But that’s not to say you shouldn’t have something a little—or a LOT—more fun in your outerwear arsenal too, and these four guys are up to the job. —erica

LEVEL I: Double-breasted and ultra-classic, this plum BLK DNM number is just two notches left of neutral.

LEVEL II: Take a standard peacoat, turn the blue up to 11, and you get this Carven sucker.

LEVEL III: So ladylike in a can’t-hold-me-back way—how sick would this Sophie Hulme guy look with black-and-white prints?

LEVEL IV: The color of this MSGM situation is majorly girly, but the boxy shape and cropped sleeves are much more salty than sweet.

Here you have it: all the “Next Level” you can handle.

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Next Level: Angora

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IT’S TIME TO GET COZY. Or, well, it almost is. And these supremely fluffy sweaters are the way to go. —erica

LEVEL I: Classic, slouchy, and just plain cool—Won Hundred knows what’s up.

LEVEL II: The persimmon color of this Clover Canyon guy is so fresh. And it’d look rad with a camel trench.

LEVEL III: Carven goes just a little crazy, but the neutral hues keep this crewneck super-wearable.

LEVEL IV: Floral satin! Neon polka dots! Emma Cook, goin’ for it.

Get in on allll the “Next Level” action right here.

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In Character: Violet Beauregarde

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Obviously when you watch Willy Wonka and the Chocolate Factory, you cheer for Charlie. But if he hadn’t gotten a golden ticket? I would have been rooting for Violet. Here, how to copy her look (before she had to be sent to the Juicing Room). —erica

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A sailor-inspired Labour of Love getup in a foreshadowing color.

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A bright red Carven belt—as attention-grabbing as her record-breaking gum-chewing.

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A fitted blue Isabel Marant jacket that Miss Cornelia Prince Medal back in Miles City, Montana, would have been toootally jealous of.

Head here to get your “In Character” fix!

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