The 19 Best Winter Dresses for 2023

Striped sweaters are a constant in my winter wardrobe, so this simple black-and-white striped wool-blend sweater dress from Zara is naturally next up on my to-buy list. The mock-neck design at the top is tighter to the neck than a traditional turtleneck, therefore making it a great layering piece under chunky sweaters. Style the midi-length hemline works well with heels, ankle boots, or knee-length boots. Plus, it retails for just under $100 and will never (ever) go out of style.

This best-selling (and affordable!) light gray mini sweater dress from Lulu's is great if you want the look and feel of a traditional sweater dress but still want to show some leg. It fits just a touch oversized, so it’s great for low-effort outfit days. Style it over a pair of opaque tights with knee boots or with fishnet tights with heels. You can also belt it to add some shape if so you choose. Shop it in four other colors, including maroon, camel, and navy blue. 

Wearing white in the winter time is not only acceptable but encouraged in my mind. This mini skater-style dress from Mango is begging to be layered under a chunky knit and worn over tights with boots. The lightweight ribbed fabric won’t make you overheat under your layers, and the sleek mock-neck neckline makes it easy to wear it with several necklaces in your preferred metal. For under $50, you won’t find a cuter and more easy-to-style piece this winter season.  

"This Zara dress is what I call a low-effort, high-payoff piece. The draped sheath design is effortlessly polished in that all I need to do is slip this slinky number on, and I automatically feel ten times cooler and more put-together than I actually am. Thus far, I've already worn it to the office (I teamed it with my new favorite ballet flats and a lightweight cardigan) and a formal-ish cocktail party (paired with slingback heels, tights, and my go-to silver drop earrings)." — Emma Childs, Style Editor

Winter is officially holiday party season—and feathers are one of this year's biggest and boldest dress trends. This black velvet mini from LIKELY is available to shop in either a classic black shade or this pretty baby pink colorway. Forget about accessories like flashy earrings or necklaces—wearing this midi-length frock is a one-stop-shop for drama without all of the effort. Just pair it with your usual pair of classic heels or pumps for a fun look that still feels elevated. 

Cashmere dresses like this one from Reformation are basically just cashmere sweaters' chicer, warmer older siblings. You can shop this very chic midi dress in two other neutral shades other than black—a dove gray and a deep emerald green—but a little black dress will always have serious mileage in your wardrobe and is therefore very much worth the investment. It has a slightly ribbed texture, a body-skimming fit and a slightly flared shape at the bottom which makes walking fast (and taking longer strides) possible and comfortable.

You already love Hill House Home’s selection of best-selling and cult-favorite Nap Dresses because they’re so comfortable, but this one—The iconic Ellie in Blue Velvet—is just as festive as it is easy to style. You can shop it in sizes XXS to XXL now. My favorite way to style it for the wintertime is to layer it over a  turtleneck—sheerer options are more on trend for 2022, but your usual cotton pick in a shade like white or cream also works for a classic feel. 

You can never have too many slip dresses in your life, and this chocolate brown version from Vince is proof. While wearing one on its own might not be the smartest choice in the winter, you can totally style it under a cashmere sweater for maximum luxurious vibes or over a T-shirt or turtleneck to add extra warmth. The draped neckline on this slip dress also means that it’s a great option for wearing under a blazer to the office.

More colors, more fun! This Shoko Sweater dress from editor-approved brand STAUD is one of the brand's best-selling styles for a reason: It's versatile, comfortable, easy to wear with all different types of shoes thanks to the fact that it includes two colors rather than one (white sneakers! Black boots! A colorful pair of heels!). Shop it in this neutral colorway or in other, brighter options on the site now, like a pink-and-red combination and a lavender-and-navy-blue version.

I'm mad about plaid this season, and this T-shirt dress from Everlane is a casual way to include it into your rotation this cold weather season. Plus, the looser silhouette is so comfortable, so you won't feel like you're any more dressed up. Or, shop it in black if you're not sure about testing out that much color. 

The Line by K has been one of my cult-favorite brands for years. The pieces are supremely comofortable, supportive enough to where I don't always feel like I need a bra, and lined in the chest area to keep anything from peeping through the fabric. This olive green midi is a great way to wear a cut-out dress in the winter time because you can easily cover up the exposed skin with a scarf or the collar of a jacket if you get too cold. 

I'm not normally one for color, but this floral midi dress from RIXO is changing my mind the more time I spend looking at it. It's what I love to call "winter floral" because it includes shades like navy, cream, and a pop of red for added interest. Plus, the dress does all the preverbal talking in this outfit: keep the rest of your accessories simple. If you are in the mood to wear something colorful, pick a pair of earrrngs, a ring, or a necklace that comes in the red shade from the dress—or get as close to it as you can. 

A denim dress—especially this mini version from & Other Stories—is a great way to incorporate color into your winter wardrobe without actually putting much effort in. It's like your favorite pair of blue jeans got a fancy makeover. 

There's one thing you should know about me: I love a sequined party dress. This one from J.Crew caught my eye because of the structured detailing at the top and the side slit on the leg. It's sexy without feeling over the top, and accessories aren't even needed.

I personally own five of these two-in-one dresses from Allsaints. The sweater and the slip dress underneath can be worn on their own or together, so you're honestly getting four outfit possibilities with one single purchase. This silver "tinsel" option is the official cool-girl holiday dress.

Simply put, I hate putting effort into my winter ensembles. This nylon dress is so lightweight, so It's obviously on my winter shopping list. Wearing a lightweight dress in the winter might sound intuitive, but think of it this way: you can layer anything you want underneath it, from fleece-lined leggings to a black turtleneck, without overheating. 

Leather (or faux leather, in this case) is practically synonymous with fall and winter weather in my book. This tank dress is perfect for the person who wants to look cool and festive at their next holiday party rather than wear a ton of color. Like the velvet Hill House Home Dress, the luxe leather material is what makes this feel winter-appropriate, so you never look like you're doing too much. 

Not all winter dresses need to come in neutral shades like brown, black, or navy blue. This brightly-printed orange maxi dress from FARM Rio can work for either winter or summer depending on the accessories that you choose to style it with, but I'm imagining this with a pair of black pumps and a matching handbag in the colder months this year.  The smocked details in the mid-section are also going to make this a tad more comfortable than others on your list. 

Yes, you've already heard of wearing cardigans in the winter—but have you heard cardigan dresses? If not, allow me to introduce you to this cozy and cute pick from Hanifa. The brand’s show-stopping cardigan dress feels as cozy as your bathrobe with an infinitely more polished look. It's hand-knit from Korean acrylic yarn and comes in nine colors including this purple shade, a bright red,a and a Kelly green —choose your favorite hue or a pick up a few.