How to Wear Dresses in the Winter Without Getting Frostbite (2024)

From Hanukkah to Christmas and New Year's Eve to Valentine's Day, it can be argued that the fanciest holidays fall during the coldest months of the year. Freezing temperatures can make getting dressed up a struggle, and even if you aren't attending a special celebration, it can be tough to figure out how to wear dresses in the winter. Colorful tights and winter leggings are trending solutions that might add a bit of warmth, but they're not the only ways to make those minis, midis, and maxis work on days when you can see your breath.

Ahead. we're rounding up our best winter dress outfit ideas, ensuring that no matter where you're headed, you'll feel comfortable while looking cute.

Swap Out Your Shoes

Rather than reaching for ballet flats or your favorite pair of sneakers, go with boots that hit just below or over your knee. It's a sneaky yet sleek way to shield your legs from harsh winds. Plus, if you opt for a longer-length dress or add a pair of tights, you'll have even more coverage.

Add a Vest

Another way to wear dresses in the winter is by layering up. While blazers are always a smart move, a vest will also add some interest to your outfit. Sweater, puffer, structured, choose a style that speaks to you. To take this look to the next level, opt for a monochrome color palette—the bolder and brighter, the better.

Invest in Cozy Outerwear

Don't pack up your sundresses just yet. Adapt your favorite summery frock to the cooler months by simply layering it with winter outerwear. A neutral faux fur coat is a must-have this season and will go with any dress of your choosing.

Layer With a Turtleneck

A simple black turtleneck is the ultimate layering piece—just look at this outfit as proof. Not only will it keep you warm but it will look super chic, too. Combine with knee-high boots and throw on a colorful knit for a hit of dopamine.

Embrace the Sweater Dress

Neutral sweater dresses happen to be a classic winter staple—but don't overlook the details. Cinching your waist with a belt will flatter your figure while wearing tights will lend you some extra warmth. A pair of chunky boots will also add interest and make trekking through slush and snow a little bit easier.

Get Creative With a Blazer

Oversized everything is having a moment—blazers included. Reach for a roomy fit and forgo the pants to land an on-trend blazer dress look like Ashley Park here. Finish with tights and a pair of chunky platform loafers and be prepared for the compliments to roll in.

Pull Double Duty

Sometimes, the best winter outfits come from thinking outside the box. For instance, a blazer or oversized shirt can double as a dress, while a dress can become a skirt with the help of a sweater. Simply layer a knitted or embellished option over your look for a warm ensemble that also makes the most of what's already in your closet.

Break Out the Accessories

Never underestimate the power of accessories. Their purpose is two-fold: adding some flair to your outfit and in the case of gloves and hats, creating warmth as well. Slip on a pair of opera gloves and a beanie to earn extra style points and show off your seasonal know-how.