Date Night
Feb 4, 2019

These First-Date Winter Outfits Sure to Impress

by Eva Thomas

First dates are nerve-racking—for everyone. Planning what you'll do, figuring out what to wear, and hoping that initial encounter isn't, well, awkward—it's all part of what makes meeting someone for the first time so stressful. But one way to reduce said stress and nerves is to wear something that you feel 100% comfortable in, and that's exactly where we come into play. We're here to help you plan and perfect your first-date winter outfits and provide you with easy-to-follow formulas you can always turn to when you find yourself in a dressing rut.

We scoured our vast network of in-the-know fashion girls to pick out our favorite looks that are guaranteed to make a great, lasting impression when meeting someone for the first time. Ahead, see our roundup of cute first-date winter outfits; then shop our edit date essentials.

First-Date Winter Outfits

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A polka-dot dress is a fun pick for a casual winter date.

Cute First-Date Winter Outfits

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Try a sweater-and-skirt pairing for a chic first-date winter look.

Easy First-Date Winter Outfits

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White pants and a sleek blouse make for a great first-date look you can wear for a casual coffee or a nighttime dinner.

First-Date Winter Outfits

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Try an LBD with knee-high boots.

First-Date Winter Outfits

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Or a maxi dress with slouchy white boots.

Chic First-Date Winter Outfts

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@fundachristophersen

Perfect laid-back yet put-together.

Cute First-Date Winter Outfits

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Show off your fun side by pairing unexpected colors like lilac and bright red.

First-Date Winter Outfits

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An oversize sweater and jeans make a fail-proof first-date pick.

Chic First-Date Winter Outfits

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@brittanyxavier

Throw a moto jacket over this checkered miniskirt–and–white tee combo to make it slightly more weather-appropriate.

First-Date Winter Outfits

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For a casual daytime winter date, style your favorite jeans with a button-down blouse and black booties.

Chic First-Date Winter Outfits

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@josephinebredsted

This is a cute yet practical first-date outfit that's certain to impress.

First-Date Winter Outfits

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@kellyaugustineb

For a fancy dinner date, don your favorite midi dress and heels. Top off the look with a colorful coat.

Isa Ribbed Merino Wool Turtleneck Sweater

Isa Ribbed Merino Wool Turtleneck Sweater

Wear this with blue jeans or black denim.

Ruffled Printed Silk Crepe De Chine Wrap Top

Ruffled Printed Silk Crepe de Chine Wrap Top

A wrap blouse you can easily dress up or down.

501 Skinny Jeans

501 Skinny Jeans

A forever pair of jeans.

Hartley Boots

Cool black boots that you can walk miles in.