4 Ways to Dress Up Your Winter Staples for a Night Out

By now, you've probably got your winter daytime look sorted. You've figured out that the key to looking polished—and not like the Michelin Man—is a few good layers and resisting the temptation to just belt a sleeping bag and call it a day. But looking cute after-hours when it's freezing? That requires more thought, not least because most of your cold-weather workhorses don't exactly say "sexy" (hello, turtleneck). So we took four chill-busting items that are probably already in your regular rotation and put an evening spin on them—bookmark this for your next date night.

The Leather Midi Skirt

How you wear it during the day: paired with a peacoat, classic oxford, pointed-toe pumps, and a stack of mixed metal bangles.

How you wear it at night:

Tibi Leather Full Skirt ($599, tibi.com); Iro Luciana Knit Collar Moto Jacket ($1,298; intermixonline.com); H&M Short Sequined Top ($25; hm.com); Stuart Weitzman The Heist Pump ($375; stuartweitzman.com); Everlane The Petra Clutch ($198; everlane.com); Stella & Dot Pave Chevron Ring ($29, stelladot.com).

The Knit Turtleneck

How you wear it during the day: under a comfy sweater and varsity jacket, coordinated with basic jeans, slip-on sneakers, and an array of delicate midi rings.

How you wear it at night:

Uniqlo Heattech Turtle Neck T-Shirt ($7.90; uniqlo.com); Mango Unstructured Oversize Coat ($130; shopmango.com); rag & bone March crepe-trimmed velvet blazer ($595; netaporter.com); Saint Laurent Faux Leather Trousers ($450; farfetch.com); Vince Camuto Caden Bootie in Black Snake ($55; nordstrom.com); Valentino the Rockstud Leather Shoulder Bag ($1,195; saksfifthavenue.com); Dean Davidson Ingot Studs ($145; deandavidson.ca).

The Faux Fur Vest

How you wear it during the day: layered with a leather jacket and a striped shirt on top, extra slim jeans and over-the-knee fitted boots on the bottom.

How you wear it at night:

Topshop Faux Fur Gilet Vest ($90; topshop.com); COS Printed Tunic Dress ($135; cosstores.com); L'Agence Notch Collar Coat in Camel ($795; shop.lagencefashion.com); Wolford Tights ($55; wolfordshop.com); Zara Round Toe Court Shoes ($70; zara.com); Eddie Borgo Rose Quartz Rose Gold Cone Bracelet ($325; neimanmarcus.com); Baublebar Snowball Pearl Collar ($42; baublebar.com).

The Track Pant

How you wear it during the day: with a boucle coat, solid crewneck, brogue shoes, and a bright statement necklace.

How you wear it at night:

Prabal Gurung Wool-Gabardine Track Pants ($375; modaoperandi.com); MSGM Floral-Print Woven Cotton Coat ($763; matchesfashion.com); Theory Vaneesa O Top ($190; theory.com); Jennifer Zeuner Nazar Lariat ($158; revolveclothing.com); SJP by Sarah Jessica Parker Fawn pump ($375; zappos.com); Alexander Wang Chastity Miniaudiere Clutch ($371; alexanderwang.com).

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