Winter Fashion 2023
Feb 2, 2024

31 Pretty Date-Night Tops You Can Actually Wear in the Winter

by Caitlin Burnett

Dressing for date night can be quite the conundrum under normal circumstances, but that increases tenfold in the winter. You want to feel polished and elegant while still remaining comfortable (but also effortless)—it's a tall order. When you factor in frigid temperatures, the outfit puzzle suddenly feels impossible.

Enter the pretty top. It's a classic for a reason, as it pairs well with everything from maxi skirts to tailored trousers. But not just any top will work when you consider the low temperatures and layers of outerwear. I have a system for gauging if a top will work well for those winter nights out: Either it has sleeves, or it has a material or neckline that looks nice under a jacket. As long as it meets one of those criteria, I can rest assured I'll be comfortable for wherever the evening takes me. Since we're still in peak winter and approaching Valentine's Day, I'm highlighting 31 cute winter tops perfect for date night.

Toteme Slip Through Knit Top

Slip Through Knit Top

The only word that comes to mind is chic.

DISSH Jovie Black Long Sleeve Top

Jovie Black Long Sleeve Top

A subtle way to show a bit of skin.

Reformation Melanie Top

I just love this color combination.

Sophie Rue Triomphe Top

Off-the-shoulder tops are back.

Norma Kamali Slim Fit Turtleneck Top

Slim Fit Turtleneck Top

Talk about a versatile winter top.

Reformation Allegra Sweater Tank

Allegra Sweater Tank

We love a built-in accessory.

Zara Exposed Shoulder Top

Exposed Shoulder Top

Pair this with bold earrings.

Mango Maxi-Flower Halter Top

Maxi-Flower Halter Top

Rosettes are still going strong.

Gaâla Esme Corset Top

Esme Corset Top

This neckline was made to be paired with a coat.

Camila Coelho Delaine Top

A unique twist to an off-the-shoulder design.

Commando Ballet Bodysuit

Ballet Bodysuit

I can personally attest to how flattering this bodysuit is.

Lioness Allure Strapless Top

Allure Strapless Top

Espresso brown is everywhere right now.

Reformation Nixie Knit Top

Picture this with tailored trousers.

Pixie Market Popcorn Knit Off-the-Shoulder Top

Popcorn Knit Off-the-Shoulder Top

You can just tell this fabric is cozy.

H&M Rib-Knit Sweater

Rib-Knit Sweater

I love this neckline.

Fleur Du Mal High Collar Bodysuit

High Collar Bodysuit

I never knew I needed a collared bodysuit until now.

Zara Off-Shoulder Top

Off-Shoulder Top

Just think about the accessory options with this.

H&M Bead-Detail Tube Top

Bead-Detail Tube Top

The pearl detail makes this one stand out.

The Sei High Neck Top

This just went to the top of my wish list.