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How to Wear a Dress in Cold Weather and Not Freeze

Multiple layers and the right footwear are a good start

spinner image cozy dresses for winter
(Left to right) Anne Klein Colorblock Turtleneck Sweater Dress in Camel Combo; & Other Stories Buttoned Rib Knit Dress in Pink; Pure Jill Winter Sky Midi Dress in Navy Blue Large Painted Chevron
Getty Images; Nordstrom; & Other Stories; J.Jill

Winter and early spring doesn’t have to mean pants season. Not when dresses can get us ready to rock in three minutes flat and skim over any extra pounds. Dresses are our wardrobe allies and confidence boosters all year long. But there’s one small problem: Wearing a dress when it’s bone-chilling cold can be a frosty not fabulous experience. Here are the anti-freeze secrets to surviving in style.

1. Start with a winter-worthy dress

It may be boho trendy to wear a silky slip dress with a big chunky cardigan, but no one over 50 does this in real life (unless you’re super trendy and live in L.A.). The best chill-chaser is a cozy, comfy sweater dress with long sleeves, like the Anne Klein Colorblock Turtleneck Sweater Dress in Camel Combo ($119, nordstrom.com) or the & Other Stories Buttoned Rib Knit Dress in Pink ($139, stories.com/en_usd) in a just-below-the-knee to mid-calf/midi length. Don’t like sweater dresses? Any long-sleeve midi dress in a dark print, like the Pure Jill Winter Sky Midi Dress in Navy Blue Large Painted Chevron ($119, jjill.com), is a perfect runner-up.

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spinner image Journee Collection Comfort Foam Vellia Boot, Extra Wide Calf, in Taupe; Josef Seibel Selena 21 in Castagne; Trotters Kirby Knee High Boot in Black Croc Print Leather
(Left to right) Journee Collection Comfort Foam Vellia Boot, Extra Wide Calf, in Taupe ($85, zappos.com); Josef Seibel Selena 21 in Castagne ($220, zappos.com); Trotters Kirby Knee High Boot in Black Croc Print Leather ($160, nordstrom.com)
Zappos (2); Nordstrom

2. Swap shoes for tall boots

Hold the ballet flats, mules, pumps and sneakers, and pair your dresses with sleek knee-high boots. Whether you choose leather, moc croc, suede or a stretch fabric, taller boots give any dress a dash of attitude (and are also a major trend this winter). For a dressier effect, opt for block or kitten heels instead of flat or lug soles.

spinner image LifeStride Zeppelin Boot in Grey; L.L. Bean Women’s Silk Pointelle Long-Sleeve Scoopneck in Cream; Barbour Burne Long Sleeve Wool Blend Sweater Dress in Aran; Quince Baby Alpaca-Wool Cropped Cardigan in Charcoal; Spanx Tight-End Tights in Charcoal
(Clockwise from bottom left) LifeStride Zeppelin Boot in Grey ($60, dsw.com/en/us); L.L. Bean Women’s Silk Pointelle Long-Sleeve Scoopneck in Cream ($55, llbean.com); Barbour Burne Long Sleeve Wool Blend Sweater Dress in Aran ($175, nordstrom.com); Quince Baby Alpaca-Wool Cropped Cardigan in Charcoal ($60, onequince.com); Spanx Tight-End Tights in Charcoal ($28, spanx.com)
DSW; L.L.Bean; Nordstrom; Quince; Spanx

3. Make a layer sandwich

Weatherproof your dress by adding a thin silky thermal tee or bodysuit and tights beneath for extra insulation. Seal in the warmth with a top layer — sweater or jacket. Pay attention, though, to what shows at the neckline and hem. You don’t want to wear a moc neck bodysuit under a V-neck dress. Be sure to tone tights to the dress or boots. Black opaque tights may be your usual go-to, but they only work if you’re wearing a black dress or black boots.

spinner image Zaful Women’s Cropped Turtleneck Sweater with Lantern Sleeves in 1-Deep Brown; Boden Scoop Neck Ribbed Dress in Park Ranger; Fuinloth Women’s Padded High Collar Puffer Vest in Brown
(Left to right) Zaful Women’s Cropped Turtleneck Sweater with Lantern Sleeves in 1-Deep Brown; Boden Scoop Neck Ribbed Dress in Park Ranger; Fuinloth Women’s Padded High Collar Puffer Vest in Brown
Amazon; Boden; Amazon

4. Turn a dress into a skirt and sweater duo

Cardigans are not the only cold-snap option. You can get shiver-free benefits from your favorite pullovers, too, just by faking the look of separates. Wear your toastiest sweaters — even turtlenecks — right over dresses to create a skirt look. You might slip a cropped sweater like the Zaful Women’s Cropped Turtleneck Sweater with Lantern Sleeves in 1-Deep Brown ($36, amazon.com) over the Boden Scoop Neck Ribbed Dress in Park Ranger ($180, bodenusa.com/en-us) and even add a trendy cropped puffer vest like the Fuinloth Women’s Padded High Collar Puffer Vest in Brown ($28, amazon.com) over that duo. Toasty as a duvet.

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spinner image Ann Taylor Double Breasted Sweater Blazer in Toasted Oat; Talbots Collarless Jean Jacket in Vintage Indigo; Quince 100% Leather Stand-Collar Jacket in Cognac
(Left to right) Ann Taylor Double Breasted Sweater Blazer in Toasted Oat ($149, anntaylor.com); Talbots Collarless Jean Jacket in Vintage Indigo ($119, talbots.com); Quince 100% Leather Stand-Collar Jacket in Cognac ($149, onequince.com)
Ann Taylor; Talbots; Quince

5. Wear a modern “inside” jacket over your dress 

Many women are in the habit of throwing an old tailored blazer (usually in navy or black) over a dress day or night for additional warmth. It’s good in theory, but it looks dated and fussy with “lifestyle” dresses like fluid jerseys, soft knits and midis. Substitute a buttery leather jacket, a cropped collarless jacket or a knit blazer hybrid instead and say buh-bye to goose bumps.

spinner image Impo Namora Boot in Beige/Brown/Black Animal Print Faux Suede; Zesica Women’s 2023 Long Sleeve Open Front Soft Knit Cardigan Sweater in Black; French Connection Soft Crewneck Sweater Dress in Camel; Asos Design Curve Knit Midi Dress with Tie Waist in Taupe; H&M Women’s Trench Coat in Black
(Left to right) Impo Namora Boot in Beige/Brown/Black Animal Print Faux Suede ($70, dsw.com/en/us); Zesica Women’s 2023 Long Sleeve Open Front Soft Knit Cardigan Sweater ($50, amazon.com); French Connection Soft Crewneck Sweater Dress in Camel ($98, bloomingdales.com); Asos Design Curve Knit Midi Dress with Tie Waist in Taupe ($50, asos.com/us); H&M Women’s Trench Coat ($75, www2.hm.com/en_us)
DSW; Amazon; Bloomingdale's; ASOS; H&M

6. Stick to a color theme

Supplementing a dress with “extras” is the best antidote on icy days. But when pulling together a look, limit the colors you’re combining. You might opt for a monochromatic look and dress head to toe in one color, or maybe mix two neutrals, like beige and black. This strategy speeds up the dressing process, makes mixing sporty and casual or feminine and edgy pieces easier, and always looks chic not choppy in the end.

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