Winter Travel Outfits: Stay Chic and Cozy on Your Holiday Adventures

Posted by Aleyna Keskin on

Cue the holiday tunes because it’s the most wonderful time of the year! The holiday season tends to bring some of the busiest travel days in the United States. It’s no wonder more than 7.5 million people travel during the holidays. This time is meant to be spent celebrating the end of another year with loved ones. 

Whether you’re visiting family in your hometown, traveling for vacation, or exploring a new city, we’re going to share the best winter travel outfits. Packing for your winter travels doesn’t need to be a challenge this year. With our tips, you can learn to balance warmth, comfort, and style when choosing travel outfits.

In this article, we will cover how to build a winter travel wardrobe, share outfit ideas for various holiday occasions, and provide packing tips to ensure smooth travels. 

Building the Perfect Winter Travel Wardrobe

Nothing’s worse than realizing you should have spent time planning outfits instead of just throwing your whole closet into a suitcase. To avoid the panic of asking yourself, “What am I going to wear?” take the time to build your winter travel wardrobe in advance. 

To build an effective winter travel capsule wardrobe, focus on foundational pieces. These include warm base layers such as thermal long-sleeve tops and fleece-lined leggings. Be sure to also pack versatile mid-layers like knit sweaters or cardigans for added warmth. Lastly, you should bring stylish outerwear like a puffer jacket and a wool or cashmere coat

By packing all the basics, you can lay the foundation for many fashionable outfits. Additionally, save space in your luggage by packing versatile pieces you can mix and match. Don’t underestimate the power of accessories for winter travel outfits. Bring your favorite winter accessories, such as beanies, silk scarves, and belts, to elevate your outfits.  

To break things down further, here is an example of a clothing packing list for a four-day holiday trip.

  • (1) pair of leggings
  • (1) pair of jeans
  • (1) sweater dress
  • (2) long-sleeve tops
  • (1) cardigan
  • (1) oversized sweater
  • (1) fitted sweater
  • (1) maxi skirt
  • (1) tailored coat
  • (1) puffer coat

Cozy and Casual: Travel Day Looks

There’s nothing better than picking out the perfect travel day outfit. When traveling, you should prioritize comfort to ensure you have a pleasant experience and arrive happy. We’re going to share a couple of travel day outfit ideas for cold weather. 

Outfit 1: If you are going to be spending all day in the car or flying from airport to airport, you want to be comfortable yet stylish. One outfit idea that’s ideal for a long travel day is a pair of leggings or joggers with an oversized sweater and sneakers. Complete the look with a cute shoulder bag or backpack serving as your “personal item” for a long flight. 

Outfit 2: For a less intense travel day, you may feel confident wearing something a little less casual. Let’s say you’re going directly to a restaurant for dinner with your family after you arrive. You could wear a long cardigan over a fitted turtleneck with straight-leg jeans. Finish this style with your go-to shoes or a pair of ankle booties and your favorite gold jewelry.

Bonus Tip: Layering clothes is great for travel days when you may encounter fluctuating temperatures on flights or long drives. This way, you can remove layers if you get too warm or vice versa.

Exploring in Style: City Travel Outfits

Once you’ve arrived at your destination, it’s time to hit the town! Exploring cities like New York or Chicago during the holidays can be like walking in a winter wonderland. Just be sure to bundle up enough to stay warm and cozy when the temperature drops at night. 

Here are a couple of outfit ideas perfect for exploring winter cities with family or friends. 

Outfit 1: For a chic look, try wearing a knit midi dress with fleece-lined tights underneath. Pair this with ankle boots and a tailored wool coat, and you’ll have a stylish outfit. To ensure you stay warm when walking outside, consider a cashmere scarf and leather gloves. 

Outfit 2: Another city travel outfit idea is to wear high-waisted trousers with a tucked-in knit sweater and a silk scarf. Depending on the temperature, add a puffer vest or down jacket for extra warmth. Pair the outfit with comfortable shoes such as loafers or sneakers. 

Bonus Tip: We recommend adding a crossbody bag and gloves to your city travel outfits for practicality and flair. 

Adventure-Ready: Winter Outfits for the Outdoors 

What’s a winter holiday trip without getting outside a bit? When packing for your trip, include options for outdoor activities such as hiking or visiting Christmas markets. These outfit ideas balance practicality and style for outdoor adventures. 

Outfit 1: If you are taking a quick day hike with your loved ones, we suggest wearing a moisture-wicking thermal base layer, a pair of fleece-lined leggings, a cute hoodie, and a puffer jacket. Finish the look with a pair of wool socks and waterproof boots to keep your feet warm. 

Outfit 2: For an outdoor holiday market or festival, we recommend wearing a cashmere sweater layered under a vest and your favorite pair of jeans. If you are in a colder climate, consider wearing thermal leggings under your jeans. As for accessories, you can’t go wrong with wool socks, mittens, and a knit beanie. 

Bonus Tip: To dress for warmth without compromising on style, focus on finding pieces made from quality winter fabrics such as wool, cashmere, and flannel.

Elegant Winter Looks for Holiday Evenings

Whether it’s a New Year’s Eve get-together or holiday dinner party, you probably will have at least one evening event on the books. Dressing up during winter trips lets you showcase your style and create elegant looks. Consider these evening outfit ideas for your upcoming holiday travels.

Outfit 1: Looking for something stylish, fun, and flirty to wear? Try a velvet wrap dress paired with knee-high boots and a tailored coat. This combination is an excellent option for a New Year’s Eve party. 

Outfit 2: For a holiday dinner party, wear a solid-colored jumpsuit styled with a faux fur jacket for added drama. Throw on some strappy heels and a pair of statement earrings to enhance the outfit. This look is sophisticated yet comfortable for a fun night with family or friends. 

Bonus Tip: Don’t forget to accessorize your evening ensembles! Bold jewelry or a bejeweled clutch can truly make all the difference.  

Pack Smart: Tips for Winter Travel Wardrobes

So, with all of these winter outfit ideas swirling in your head, you’re probably wondering how you’re going to pack everything. Packing with intention is the key to not overstuffing your luggage with unnecessary items. 

Check out these winter travel packing tips: 

Roll clothes to save space. Rolling clothes has been proven to be an effective space-saving packing technique. It also helps keep clothes from wrinkling in your bag. Choose neutral colors. By choosing neutral colors, you can maximize your outfit combinations and potentially wear the same pieces multiple times. Include travel-friendly accessories. When choosing what accessories to bring, consider foldable hats or compact scarves. These travel accessories don’t occupy too much space in your carry-on suitcase.Prioritize versatile layering pieces. When packing, prioritize pieces you can layer in different outfits to stay prepared for any type of weather. It’s best to pick clothing you can mix and match to create many stylish outfits. 

Explore Porterist’s Collection for Your Perfect Winter Wardrobe

We hope this guide helped you better prepare for your winter travel. Remember to focus on foundational pieces you can layer when building your winter travel wardrobe. Plan your holiday travel looks with confidence by using our tips and outfit ideas. 

Porterist has everything you need to create the best winter travel wardrobe. From sweaters and dresses to accessories and shoes, shop Porterist this holiday season.

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