32 Winter Dresses That You Can Wear All Season Long

Velvet and pockets? We just hit the winter dress jackpot.

The perfect frock for when you’re sick of looking like a marshmallow.

Just a little spandex in this knit weave goes a long way (especially on Thanksgiving).

Below 30 outside? Bring spring to you.

The effortlessness of a tie-neck peasant dress paired with stockings can’t be overstated.

Ooh, or you could wear a polka-dot nightgown with tights and boots and call it a day (or night). 

Dress up this swingy tie-waist midi with heels, or dress it down with slouchy boots. 

Like your favorite pullover sweater...in made-from-sustainably-sourced-cashmere dress form.

And you thought cold-weather dressing meant dowdy and frumpy. (Just don’t forget to break out your razor before wearing.)

The cheetah-print midi skirt you’re seeing all over your Insta feed, winterized. 

Buy It ($550)

There are exactly 973 ways to style this dress (and, thankfully, wayyy fewer days in winter).

A stretchy, long-sleeve, colorblocked dress is a sartorial smoke screen for winter blues.

Fuchsia florals in winter? Groundbreaking (but actually). 

The velvet sheen of this dusty lavender number makes it dressy enough for a party, but the relaxed silhouette makes it chill enough for weekend brunch.

Wool cocoon coat or not, we guarantee you won’t sweat your brains out the moment you step into artificial heat in this swingy, semi-sheer number. 

Square neckline? Check. Bishop sleeves? Check. Pockets? Check.

When even the simplest of layering feels exhausting, you can absolutely cheat on all your plain white turtlenecks.

Mark our words: Moody florals are the easiest way to break out of a style rut. 

Or embrace seasonal stripes and don a tartan fit-and-flare with an oversized blanket scarf and booties.

The ’90s are fully back, courtesy of this rust corduroy mini.

Pop quiz: Pair this with brown boots? Black boots? White boots? (Hint: Any of the above.)

Buy It ($498)

Your winter whites just got a serious upgrade with this ribbed-knit number featuring a comfy mock neck and flattering front pleat. 

Don eye-popping purple and red like a duchess. 

A removable tie-waist belt lets you choose from various styling options for this 100% silk dress.

Buy It ($285)

Because a sophisticated double-breasted silhouette doesn’t have to come in pantsuit form—or cost an arm and a leg for tailoring.

On days when you absolutely cannot be bothered to wear another scarf, just zip up the front of your dress and be on your merry way.

Drape it over a turtleneck and slouchy boots for winter, throw it over your bathing suit while lounging poolside in summer.

The Goldilocks of sweaterdresses: Not too short, not too thin and not too hot.

Throw on this autumnal-hued dream with flattering bodice ruching when you're sick of baggy sweaters and oversize coats.

It’s called the “everyday” dress for a reason, people. (BRB, buying one in every color.)

This burgundy floral beauty can be worn off the shoulder, too, for a dressier look

Buy It ($395)

And you thought we’d forget you, lady who only wears black all year long.

Buy It ($249)