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Travel + Leisure / Reese Herrington
Winter dresses definitely deserve a spot on your cold-weather packing list, especially with après ski season, winter weddings, and fancy vacation dinners on the horizon. If you’re gearing up for winter travel and plan to embrace these chilly adventures in style, you’re going to need winter dresses that are cozy enough for you to brave the low temperatures and comfy enough to rock on the go.
Luckily, Amazon has tons of travel-friendly, best-selling winter dresses that fit the bill. Whether you’re on a plane, at the office, or having a fireside chat at the ski lodge, these versatile looks will offer a break from your everyday winter wear. Read on for the best-selling Amazon dresses that are comfortable, packable, and easy to move in — and best of all, under $50.
Related: The 10 Best Ski Jackets for Women of 2023, Tested and Reviewed
A great après ski look or dinner-at-a-lodge look, this winter dress is both casual (thanks to the soft fabric) and stylish (thanks to oversized buttons). The swingy shape keeps the fit loose, easy, and forgiving. Hitting just above the knee, this dress can be paired with tights or cotton leggings and boots. Throw on a jean or a leather jacket on top for additional coverage. Supremely soft fabric keeps this a cozy option for any travel moment. Plus, it’s machine washable and available in S to XL sizes in 36 colors.
“A great travel outfit,” shared one commenter who said the dress is, “soft, cozy, [and] not too warm. My go-to for travel, throw it on with a pair of leggings and hop on the plane.”
To buy: amazon.com, $35 (originally $37)
If you’ve got a more formal occasion planned during your travels, this dress is the perfect piece to pack. With just the right amount of style, thanks to the deep v-neck, and the right amount of elegance, thanks to long sleeves, it's ready for a special event. At the same time, the material is smooth and flexible, keeping the fit relaxed and casual.
One customer shared, “It’s beautiful and soft and will pack in a suitcase without wrinkling — which is a plus for this business traveler.” They continued, “It’s so flattering on that I’ve decided to wear it to my son’s wedding in January, which says a lot since I was prepared to pay around $500 for a designer dress.”
To buy: amazon.com, $21 (originally $35)
From work meetings to happy hour, this desk-to-drinks winter dress is a must-own. The pencil skirt and self-tie belt lend a polished look for work travel, yet it’s a piece you'll want to take on vacation, too. Switch up your shoes and accessories, add your belt, and the look can be completely different.
This versatile dress has more than 7,000 five-star ratings, with many discussing how great it is for trips. One shopper raved that it’s a “super cute and comfortable dress,” continuing it has a “very flattering style, and soft, yet stretchy fabric,” which is an essential quality for traveling. Plus, they noted, it has a high-quality feel.
To buy: amazon.com, $35 (originally $44)
Related: This Is the Only Cold-weather Packing List You Need This Winter
Nothing looks and feels more appropriate for winter than cable knit. While the design of this dress is classic, the oversize sleeves make it a more modern, trendy piece. Winter white feels right, or choose from one of the rich blue, green, and purple shades. Since this is a chunky piece, it might be best to wear it on the plane with leggings so it doesn’t take up too much space in your suitcase. When at your destination, dress it up with booties or heels for a night out.
The adorable fit is what many of the stellar reviews pointed out. “I bought this sweater for winter events and pictures, and it’s absolutely adorable,” shared one reviewer. “It’s loose and hides some of the weight I’ve gained but doesn’t look like I’m wearing a potato sack, so [that’s] a big win.” They continued to say that “it is so soft and cozy” and “can be dressed up or dressed down.”
To buy: amazon.com, $35 (originally $68)
Constructed with top-quality cotton, this dress is soft and breathable, preventing any overheating if you have a winter coat on top. Plus, the elastic waistline makes it uber-comfortable while creating a flattering silhouette. Stretchy fabric and a looser fit make it excellent for travel, as do the pockets that make it easy to store keys or your phone. And with 45 color and print options, there’s bound to be one to show off your personal style.
With a more than 6,000 five-star ratings, this dress is well loved for its comfort. One happy reviewer shared that it’s “the perfect travel dress,” continuing, “I now own this dress in two colors because I love it so much.” They also said it “weighs practically nothing, yet it’s thick enough to not completely blow around in the wind” and “doesn’t wrinkle terribly and is easy to pair with lots of other accessories to make it more dressy or casual. Most of all, it has pockets and is super flattering. I would own this in every single color if I could.”
To buy: amazon.com, $46
Get ready for compliments in this cool, modern, and unique dress. The oversize fit is not only artsy and chic, but it's also easy and comfortable. Convenient pockets allow you to store whatever you need handy, while the turtleneck adds a bit of polish and some extra coverage. The stretchy fabric will keep it comfy for long days, whether staying cozy on a plane with flat boots or sightseeing all day in sneakers. Make sure you pack a statement necklace or two to finish off the look.
“[It’s] perfect for travel,” exclaimed one happy customer who took it on her trip to Morocco in February. “I love both the design and the drape of this medium-weight knit fabric,” continuing that during the trip and on the long flight, “It was perfect: soft, comfortable, and stylish” and “it kept me cozy but not overly warm because the funnel neck allows ventilation.”
To buy: amazon.com, $36
If easy and breezy is your travel style, then this is your perfect dress. Soft fabric, with long sleeves that are easy to scrunch up plus an elastic waist prioritize comfort, yet the look is still elegant. Hitting just below the knee, this winter dress can be worn over tights or leggings or bare legs. Plus, it has every woman's favorite feature — pockets.
“Travels well [and] rolled up,” one review stated, meaning you can unpack this dress, and it will be ready to wear without the need to iron or steam. It continued with some additional style advice, “Love the material, length, neck. Change the look with a scarf, belt, sweater, or [wear] plain.”
To buy: amazon.com, $36
Crafted in cozy knit, breathable fabric, this ribbed turtleneck dress will get you a lot of miles no matter how far you travel from home. Wear it as a dress one day and a tunic over jeans the next, and you have two looks in one. No matter how many times you wear it, it will maintain its flattering shape. Check the size chart — since it's an oversize style, you might want to size down.
“Perfecto,” exclaimed one buyer, who bought this for a trip, saying it’s “very pretty and flattering.” They also added they think it will be great for traveling because it will be easy to layer while keeping the oversized look. They also included that it “looks more expensive than it really is,” which is a wonderful bonus for a dress under $50.
To buy: amazon.com, $42 (originally $60)
While this dress has a summery look, you can winterize it by layering a flitted crewneck tee or turtleneck underneath. And it’s a flattering design, thanks to a waistband that will sit flat and won't bunch or add to your shape. Front buttons and a racerback add a bit of style and make this dress stand out among other maxis. This seasonless dress comes in 14 colors that will work come summer with sandals as it will with tights and boots during winter.
One buyer raved about how wrinkle-free this dress was, praising it for travel. “This dress was better than my highest hope for it. It’s chiffon which won’t wrinkle for travel and arrived perfect out of the bag.” They also commented how the length is on trend, so it’s a bit cropped, making it great with lace-up heels, sneakers, or sandals come summer.
To buy: amazon.com, $39
Some may opt for an oversize, ultra-comfy look to travel in, but if you want to show up looking a bit sleeker, check out this stylish bodycon sweater dress. Whether you are driving or flying, you will arrive looking your absolute best. And even though it hugs your body and every curve, the fabric is cozy and stretchy, allowing you to sit and walk comfortably. Once you arrive, add some heels for a night out to a restaurant, lounge, or bar. With 15 color options, you can find the shade that suits your cold-weather style.
One shopper shared, “The fit is very flattering and clings in all the right places.” Style with a motorcycle jacket or blazer if there is a serious chill, and you will be the most stylish traveler around.
To buy: amazon.com, $45 (originally $60)
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