cute cold weather outfit for sightseeing in a big city

Discover Chic Winter Outfits

When you’re traveling during winter, you might find yourself frustrated that you need to pack such bulky items, like winter coats and sweaters. And don’t even get us started on knee-high boots and booties that are essential to cute cold-weather outfits!

But don’t panic! Buy Outlet is here to help you create a travel-ready, cold-weather wardrobe that ensures you feel confident and sophisticated with chic winter outfits that keep you warm — no matter the temperature!

Today, we’ll be drawing our inspiration from some top celebrity style icons, as well as our current collection of designer pieces, to incorporate bold patterns, neutral colors, and laid-back aesthetics into your suitcase. So let’s dive right into packing for your next winter trip!

Packing Tips

packing for a trip

So we’ve already talked about how bulky warm winter clothing can be, which makes packing light a real challenge. Our top tip for making sure you can pack all your cute cold-weather outfits is using packing cubes. These travel accessories save space by compressing your items into smaller bags and removing all that extra air. You’ll be surprised how much you can fit into one suitcase with these space-saving tools.

Our Favorite Styles

You should have a versatile mix of clothing in your travel bag — almost like a capsule wardrobe for winter, where every piece can match with any other. Depending on the length of your trip, here are some of the must-have items to include:

  • Water-Resistant Puffy Jacket
  • Long Wool Blend Jacket
  • Leather Jacket
  • 2-3 Long-Sleeve Base Layers
  • 2-3 Heavy Layers (Think Sweaters)
  • 1-2 Dressy Blouses
  • Sweater Dress
  • Leggings
  • Dark Wash Jeans
  • Sweats
  • Sneakers
  • Boots
  • 2 Pairs of Gloves
  • 2 Scarves
  • 2 Hats

Some of the best brands for women’s winter outfits include The North FaceTommy Hilfiger, and Tahari ASL. Now, take a look at how we put together some of these essentials into cute, cold-weather outfits.

On The Plane

chic plane outfit with jacket and sweater dress

For this look, focus on comfort. You may also need to layer up, as temperatures change from your starting location to the plane, and finally, to your destination. We suggest wearing your bulkiest items to save space in your suitcase. That means your big winter coat and your knee-high boots are a must-have for this look. To make this into a cute cold-weather outfit, choose a statement-making coat that matches your shoes.

We would pair these items with a tee, a hoodie, and some joggers to ensure you stay flexible. If you don’t plan on packing any big boots, you can wear sneakers to make all that walking in the airport much easier.

For Sight Seeing

suede moto jacket for winter travel

There’s nothing better than sightseeing in wintry weather, exploring snow-capped buildings, and thinking about the promise of a warm drink at the end of the day. However, just because you want to stay warm doesn’t mean you have to compromise on style.

Think about your final layer first, as you likely won’t be shedding any layers until you go back inside. An oversized teddy coat is the perfect choice for gallivanting around town in the winter and making space for any other layers you throw on underneath. You can also opt for something edgy to create this cute cold-weather outfit, like a suede moto jacket from Style & Co. or a cropped animal print piece from INC International Concepts.

You’ll want to let your jacket be the center of attention, so keep your bottoms warm with a pair of neutral black leggings or dark-wash jeans. Finish off this chic winter outfit with merino wool socks and a beanie to match.

Out to Dinner

chic winter sweater dress and boots

You definitely need a cute cold-weather outfit for your nighttime events, especially if you plan an evening out at a fancy restaurant. We love a sweater dress for this chic winter outfit because you’ll look formal and elegant without sacrificing any warmth!

Try a form-fitting look from Vince Camuto with some patterned tights and booties, or opt for a looser ensemble from a brand like BLACK TAPE with a pair of mid-rise, low-heel boots to protect your legs from the cold.

Shop With Buy Outlet

Whether you’re ready to pack or you’re missing a few essentials for your cute cold-weather outfits, Buy Outlet is always here to help. Explore our blog for more style tips or head to our women’s selection to find the pieces you need for your next trip right now!