Cute and Stylish Winter Travel Outfits

Woman in a sweater in winter
Photo credit: Pixabay

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It can be daunting to come up with the right winter travel outfits. Bulkier items like winter coats and cardigans take up precious space in your luggage. And don’t even get me started on winter boots! Don’t panic, I’m here to help you navigate your winter wardrobe so you feel confident for your next winter trip.

With cold temperatures, it’s easy to feel uninspired by winter travel clothes. Don’t get me wrong, there’s nothing wrong with wearing leggings and an oversized sweater. The challenge becomes how to look cute while staying warm.

Personally, I draw outfit inspo from my favorite celebrity style icons. When it comes to winter outfits, Gigi Hadid ranks supreme. She effortlessly incorporates bold patterns and neutral colors into her laid-back ascetic.

If you need outfit inspiration or help building a capsule wardrobe for your winter vacation, keep reading. These outfit ideas are trendy and affordable and will keep you warm while looking like you just stepped off the runway.

Packing Tips

Naturally, winter clothes are bulky, which can make packing light challenging. Here’s a tip: Try space-saving packing cubes. These are fantastic organizational tools and are must-haves for winter travel. When planning your packing list, consider these tips to ensure your winter travel is a success.


  • Water Resistant Puffer: if you are traveling in wintry conditions, this is a must-pack to keep you warm and protected from the elements.
  • Wool blend, long jacket: if you don’t anticipate wintry conditions, a stylish, wool-blend jacket is perfect for sightseeing around town.
  • Leather Jacket/Faux Fur Bomber: great layering pieces for dressier dinners or a night out on town.


  • First base layer: 2-3 long sleeve thermal or turtleneck shirts.
  • Second layer: 2-3 heavier layers like a turtleneck sweater, cardigan or hoodie.
  • Optional: 1-2 dressier blouses for evening events.


  • Leggings: one casual pair and one dressy option.
    SheBuysTravel Tip: Try faux leather leggings with an oversized sweater and boots for an easy daytime look.
  • Jeans: 2-3 pairs of dark or light denim. Personally, I’ll do one of each for variety.
  • Loungewear: one pair of joggers or sweatpants.


  • Sneaker: 1 pair
  • Boots: 2-3 max. The style can vary pending your itinerary. Aim for an everyday boot and something dressier for the evening.


  • Gloves/mittens: 2 pairs
  • Scarves: 1-2 max
  • Beanie: 1-2 max
  • Tote: 1 crossbody bag for daytime activities

Airport Outfit

Focus on being comfortable and warm on the day of travel. If you pack more than one coat, wear the heaviest coat and boots to the airport to save space.

SheBuysTravel Tip: If you bring a puffer jacket, roll it up and squish it into your luggage. Pack travel shoes like sneakers in your carry-on and change into them on the plane.

Cute Sightseeing Outfit Ideas

There’s something nostalgic about sightseeing in the cold, wintry weather. That said, dressing for the elements does not mean you have to compromise on style!

Wearing a cute jacket is the easiest way to stay warm and look stylish. An oversized teddy coat is perfect for galavanting around town in the cold weather.

Look for merino wool socks, gloves and base layers. This fabric is lightweight, odor-resistant, and absorbs quickly. Due to the structure of its fibers, merino wool is thinner than regular wool. It keeps you warm without the added bulk. It can be pricey, but it’s worth the splurge.

You can’t go wrong with this everyday winter outfit idea.

SheBuysTravel Style Tip: Want to elevate your outfit? Try faux-fur gloves for an edgy, chic look.

ZIAI Drop Shoulder Slant Pocket Teddy Coat

Pullover Sweaters for Women

Faux Leather Leggings – Spanx

Women's Carla Winter Boots - Universal Thread™

Saddle Crossbody Bag - A New Day™

Chic, Winter Evening Outfits

Winter travel is not complete without a nighttime outfit (or two!) A travel essential is the sweater dress. Trust me, they’re going to be your best friend when it comes to cute outfits for hitting the town.

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Shoe-wise, I’m a big fan of pairing a sweater dress with a mid-rise, low-heel boot. If mid-rise isn’t your thing, ankle boots are another great option. Finally, solid or patterned tights provide added warmth while making you look effortlessly put together.

Off the Shoulder Long Sleeve Midi Sweater Dress

Allegra K Women's High Heels Pointed Toe Stiletto Heel Knee High Boots

Unique Bargains Women's Cropped Jacket Notch Lapel Faux Fur Fluffy Coat

Vegan Leather Jacket - Camel Jacket - Moto Jacket - Lulus