Photo: Richard Majchrzak/Studio D

The Comfiest Jeans
The supersoft fabric has 360 stretch technology. ($32; OldNavy.com)

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A Jacket That Does It All
Warm up to the Traversiamo jacket (originally $895, now $100 off with code MISSIONSTATEMENTLOVESOPRAH; MissionStatement.com) from actress Hilary Swank's Mission Statement line, crafted in Italy. It's a chic, cozy winter wonder that gives you plenty of bang for your buck. Streamlined and flattering, it's versatile, water- and wind-resistant and filled with a plush and toasty down. From the slopes to the streets, you'll be haute in the cold.

Adjustable Neckline
Control your coverage with the drawstring cord, which allows you to wear the collar low or high like a funnel scarf.

Removable Sleeves
When days get mild, go sleeveless and wear it as a vest.

Double Zipper
This baby is built to move in. Let up the bottom zipper for some extra room—or a little fresh air.

Detachable Pockets
Who doesn't love extra storage? Peplum pouches add a functional flair and more of an hourglass shape.

Cinched Shape
Princess seams help create a slimming silhouette.

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The Cool Girl Jacket That Goes With Everything
In the perfect gray shade, with sleek monochromatic zippers, it works with jeans or a dress. Bonus: it's faux leather. (R Label by TheReset.com, $225; Shop.TheReset.com)

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The Essential Day-to-Night Piece
With always-flattering ruching, a fitted number can take you through a day of exploring and straight to dinner. ($194; Bailey44.com)

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A Classic Workhorse Button Down
This special no-iron cotton sateen shirt has a longer tunic feel. ($99; Chicos.com)

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The Wrap Scarf That Goes from Dinner to The Beach
Stay warm stylishly, in flight or out on the town. (Bleusalt Malibu est. 2017, $80; BleuSalt.com)

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Stylish and Functional Suede Slides
You'll glide through airport security in these seasonless slip-ons. ($150; TKees.com)

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The Versatile Outfit That's a Travel Go-To
In go-with-anything camel, the cardigan and pencil skirt can be worn together or separately. And they're made of ponte fabric that has both structure and give—plus, it won't wrinkle. (Cardigan, $188, and skirt, $118; FranneGolde.com)

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The Shirt That Goes With Everything
Not only is this cozy shirt made for layering, but it also gives great booty coverage. (Donna Karan New York, $95; LordandTaylor.com)