32 Winter Dresses That You Can Wear All Season Long

Admit it: Those three turtlenecks you keep on rotation need a break (and a good dry cleaner) stat, and your cold-weather style desperately needs a breath of fresh air. This season, turn heads in a sea of chunky cable-knits by adding a long-sleeve dress, tights and booties into the mix. Here, 32 winter dresses you can wear all season long.

Sui By Anna Sui Women's Folk Velvet Dress

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

Misa Maristela Dress

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

Love Sadie Women’s V-neck Long-sleeve Knit Dress

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

Free People Bianca Gown

Below 30 outside? Bring spring to you.

Romantic Gypsy Women’s Plus-size Long-sleeve Peasant Dress

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

Stine Goya Brooklyn Dress

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

Scoop Blouson-sleeve High-low Maxi Dress

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

Everlane The Cashmere V-neck Midi Dress

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

Aritzia Mockneck Slit Dress

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

winter dress equipment

Equipment Calanne Dress

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

Buy It ($550)

Time And Tru Cowl-neck Dress

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

Anthropologie “lorna” Midi Sweaterdress

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

Scoop Ruched-sleeve Ruffle Faux-wrap Minidress

Fuchsia florals in winter? Groundbreaking (but actually). 

Eileen Fisher Asymmetrical-hem Velvet Long-sleeve T-shirt Dress

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.

Whistles “carys” Long-sleeve Tiger-print Midi Shirtdress

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. 

Kate Spade Flair Flora Crepe Midi Dress

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

Cinq À Sept “mercer” Layered Long-sleeve Dress

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

Reformation “valentin” Dress

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

Eloquii Plaid Long-sleeve Dress

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

Madewell Corduroy Puff-sleeve Minidress

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

winter dress dvf
Diane Von Furstenberg

Dvf “tilly” Silk Crepe De Chine Midi Wrap Dress

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

Buy It ($498)

A.w.a.k.e. Mode “renton” Ribbed-knit Midi Dress

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

Boden "nerissa" Ponte Dress

Don eye-popping purple and red like a duchess. 

winter dress cuyana

Cuyana Silk High-low Shirtdress

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

Buy It ($285)

Brooks Brothers Trench Dress

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

Cos Zip-up Organic Cotton Dress

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.

Xirena “dayley” Dress

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

Bb Dakota “couldn’t Be” Sweaterdress

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

Astr The Label “cheveonne” Long-sleeve Maxi Dress

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

J.crew Long-sleeve Everyday Cashmere Crewneck Dress

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

winter dress la ligne
La Ligne

La Ligne "eloise" Dress

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

Buy It ($395)

winter dress club monaco
Club Monaco

Club Monaco Cross-front Sweaterdress

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

Buy It ($249)


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