Traveling during winter can be a magical experience—snow-covered cities, holiday lights, and cozy evenings by the fire. However, figuring out what to wear while keeping warm, stylish, and comfortable during your travels can be tricky. Whether you’re hopping on a plane, exploring new cities, or enjoying a winter vacation, you want travel dresses that are versatile, warm, and easy to pack. This winter, you don’t have to sacrifice fashion for comfort when you have the perfect travel dress.
From layering-friendly pieces to wrinkle-resistant fabrics, winter travel dresses have evolved to meet the demands of frequent travelers. In this guide, we’ll walk you through some of the best travel dresses to wear this winter, ensuring you stay chic without freezing. Whether you’re heading to a snowy mountain resort or jetting off to a chilly city, we’ve got you covered. Read on to discover which dresses will be your go-to this winter season!
Why Choose a Dress for Winter Travel?
Before we dive into our recommendations, let’s talk about why dresses should be part of your winter travel wardrobe. Dresses are easy to wear, often take up less space in your suitcase, and with the right layers, they can keep you just as warm as pants. The flexibility of dresses allows you to create different outfits by changing accessories or adding cozy layers like tights, scarves, and jackets. They’re also perfect for transitioning between casual day wear and more formal evening looks.
For those who don’t want to pack too much, a well-chosen travel dress can work for multiple occasions. With this in mind, let’s explore some of the best travel dresses that combine style, comfort, and warmth for winter trips.
1. Sweater Dresses: The Perfect Blend of Warmth and Style
Sweater dresses are a classic choice when it comes to winter fashion. Their soft knit fabric not only keeps you warm but also provides a relaxed and comfortable fit. The great thing about sweater dresses is their versatility. You can wear them with leggings, tights, or even over jeans for extra warmth. Plus, they’re easy to dress up or down depending on the occasion.
Why It Works for Travel:
- Cozy enough for cold weather.
- Packs easily without wrinkling.
- Can be layered with coats, scarves, and boots for different looks.
When picking a sweater dress for travel, choose one made from wool or cashmere for maximum warmth without bulk. Opt for neutral tones like grey, black, or beige to match with different accessories, making it easy to create various outfits with one dress.
Our Top Pick:
Item: Everlane The Felted Merino Rib Dress
Price: $195.00
- Made from 100% merino wool, this sweater dress from Everlane is both luxurious and functional. The felted texture adds extra warmth, making it perfect for colder climates, while the ribbed design gives it a modern, streamlined look. The high neckline provides additional warmth around the neck, eliminating the need for a bulky scarf. With its knee-length hem and fitted silhouette, this dress is easy to pair with boots and tights, making it an ideal option for daytime exploring or evening dinners during your winter travels.
2. Turtleneck Dresses: A Timeless Winter Essential
Turtleneck dresses are a must-have for winter, and they’re perfect for traveling because they keep your neck warm without needing a scarf. These dresses come in a variety of materials, from lightweight cotton blends to thicker wool versions, making them suitable for different levels of cold. The sleek silhouette of a turtleneck dress adds a modern touch to your winter wardrobe while remaining functional.
Why It Works for Travel:
- Provides extra warmth around the neck.
- Great for layering under jackets or cardigans.
- Can be easily dressed up with accessories.
To maximize the versatility of a turtleneck dress, go for a midi-length option. This length strikes the balance between casual and sophisticated and works well with both boots and flats. If you’re traveling to a place with unpredictable weather, layering a turtleneck dress with a long coat and knee-high boots is a foolproof way to stay warm and fashionable.
Our Top Pick:
Item: COS Ribbed Wool Turtleneck Dress
Price: $150.00
- This minimalist yet elegant dress from COS is made from a high-quality wool blend, offering warmth and durability. The turtleneck adds extra coverage for colder days, while the ribbed knit texture provides a flattering fit. The length hits just below the knee, making it suitable for both day trips and evening events. Its simplicity allows you to dress it up or down easily, and the slightly oversized fit makes it comfortable for long flights or train rides.
3. Jersey Knit Dresses: Comfortable and Wrinkle-Resistant
Jersey knit dresses are ideal for travel because of their lightweight, stretchy fabric that’s not only comfortable but also wrinkle-resistant. This makes them perfect for tossing into your suitcase without worrying about creases. Jersey knit dresses often feature a relaxed fit, which is perfect for layering with tights or leggings, and they can easily transition from daytime sightseeing to an evening out.
Why It Works for Travel:
- Extremely comfortable for long periods of wear.
- Wrinkle-resistant fabric makes packing stress-free.
- Easy to layer with jackets, coats, or scarves for added warmth.
For winter, look for long-sleeved jersey knit dresses or pair them with cardigans for extra coziness. The soft material also makes them perfect for long flights or train rides where comfort is key.
Our Top Pick:
Item: Lark & Ro Long-Sleeve Jersey Knit A-Line Dress
Price: $39.00
- This jersey knit dress from Lark & Ro offers unbeatable comfort with its stretchy, soft fabric that’s perfect for long days of travel. The A-line silhouette is universally flattering, while the lightweight material ensures you won’t feel weighed down. What’s even better? It’s wrinkle-resistant, so you can unpack it from your suitcase and wear it right away. Available in various colors, this dress is ideal for layering under coats or cardigans, and it’s easy to accessorize with scarves and boots.
4. Thermal Dresses: Practical and Stylish
If staying warm is your top priority, a thermal dress is a must-have for winter travel. Thermal fabric traps body heat, making it perfect for cold weather, especially if you’ll be spending time outdoors. These dresses are often made from a thicker material, such as fleece-lined cotton or wool blends, which helps you stay insulated.
Why It Works for Travel:
- Keeps you warm in even the coldest conditions.
- Designed to retain body heat.
- Great for layering with outerwear.
While thermal dresses are practical, they can also be stylish. Look for designs that include fun details like belts, pockets, or textured fabrics. You can easily wear a thermal dress with tights and boots during the day, then throw on a nice coat for an evening out.
Our Top Pick:
Item: Patagonia Organic Cotton Quilt Dress
Price: $159.00
- The Patagonia Organic Cotton Quilt Dress is the perfect choice for outdoor enthusiasts and eco-conscious travelers. Made from organic cotton and polyester fleece, this dress has a quilted design that traps body heat, making it an excellent option for cold weather. Its relaxed fit and subtle A-line silhouette make it both comfortable and stylish. Patagonia is known for its sustainability practices, so you can feel good about your purchase while staying warm.
5. Wool Midi Dresses: Elegance Meets Warmth
For travelers who want to look polished while staying warm, wool midi dresses are a great option. Wool is naturally insulating, making it one of the warmest fabrics you can wear in winter. Midi-length dresses offer the perfect balance between style and practicality, covering enough of your legs to keep you warm, while still looking elegant.
Why It Works for Travel:
- Provides excellent warmth without bulk.
- Elegant enough for more formal settings.
- Can be worn with both casual and dressy accessories.
Wool midi dresses are perfect for those looking to pack light but still want to make a fashion statement. Choose one in a neutral or jewel tone for maximum versatility. Pair it with ankle boots and a tailored coat, and you’re ready for anything from a museum tour to a fancy dinner.
Our Top Pick:
Item: & Other Stories Wool Blend Midi Dress
Price: $189.00
- This wool-blend midi dress from & Other Stories combines elegance with practicality, making it a great option for travelers who want to look polished while staying warm. The midi length is perfect for covering up in cold weather, while the slight flare at the hem adds movement and style. The dress is fitted through the bodice, offering a flattering silhouette that pairs beautifully with a variety of winter coats and boots.
6. Shirt Dresses: Layer-Friendly and Versatile
Shirt dresses may not be the first thing that comes to mind for winter, but they are incredibly versatile. When made from a heavier fabric like flannel or wool-blend, shirt dresses can be great for winter travel. They can easily be layered over long-sleeve tops or under chunky cardigans. The button-down style also makes them easy to adjust for different occasions, from casual daytime looks to dressier evening events.
Why It Works for Travel:
- Adjustable for both warm and cold climates.
- Can be layered for added warmth.
- Perfect for packing light while staying stylish.
Shirt dresses are great for mixing and matching with different pieces in your travel wardrobe. They also tend to have a relaxed fit, making them super comfortable for all-day wear.
Our Top Pick:
Item: Madewell Flannel Shirtdress
Price: $118.00
- Madewell’s Flannel Shirtdress is a laid-back, casual option that’s ideal for winter travel. The soft flannel material keeps you warm, while the button-down style allows you to easily adjust your look for different temperatures and occasions. The dress includes a removable belt, letting you cinch your waist for a more defined look or leave it loose for extra comfort. Perfect for layering, this dress can be worn over leggings or tights, and the plaid pattern adds a classic winter touch.
7. Maxi Dresses: Boho Meets Winter
Maxi dresses aren’t just for summer! When styled appropriately, they can be a wonderful addition to your winter travel wardrobe. Long-sleeved maxi dresses in thicker fabrics, such as wool or corduroy, offer full coverage while keeping you warm. Pair them with ankle boots and a warm coat, and you’ve got yourself a cozy yet stylish winter outfit.
Why It Works for Travel:
- Provides full leg coverage, keeping you warmer.
- Can easily be dressed up for formal occasions.
- Flowy and comfortable for long days of travel.
Maxi dresses are great if you love a bohemian look or just want something that stands out. Opt for a printed or textured design to add personality to your winter outfits.
Our Top Pick:
Item: Free People Cozy Up Maxi Dress
Price: $148.00
- The Free People Cozy Up Maxi Dress is designed with colder months in mind, featuring a blend of wool and synthetic materials that provide warmth without sacrificing the flowy, bohemian silhouette. With long sleeves and a high neckline, this dress offers full coverage, making it ideal for those who want to stay warm but love the look of a maxi dress. The subtle pattern and soft, textured fabric add a unique touch, making it stand out from basic winter dresses.
It can make you feel comfortable no matter where your winter adventures
When it comes to choosing the best travel dresses to wear this winter, comfort, warmth, and versatility are key. Sweater dresses, turtleneck dresses, and wool midi dresses provide warmth without sacrificing style, while jersey knit and thermal dresses offer both comfort and practicality. No matter where your winter travels take you, the right dress can make all the difference. Whether you’re strolling through snowy streets or heading out for a festive dinner, these dresses will keep you cozy and chic throughout your journey.
Ultimately, winter travel doesn’t have to mean bundling up in bulky, shapeless layers. With the right dresses in your suitcase, you’ll stay warm, look great, and feel comfortable no matter where your winter adventures take you. So, pack wisely, and enjoy the chilly season with style!
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