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).
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 sweater...in 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.)
Equipment Calanne Dress
The cheetah-print midi skirt you’re seeing all over your Insta feed, winterized.
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.
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.)
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.
Cuyana Silk High-Low Shirtdress
A removable tie-waist belt lets you choose from various styling options for this 100% silk dress.
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.)
La Ligne “Eloise” Dress
This burgundy floral beauty can be worn off the shoulder, too, for a dressier look