Top Winter Traveling Outfits that are both Cool & Comfy

If you love traveling in winter, you know how difficult it can be to choose the right clothes. That’s if you’re not planning a winter holiday in the sunny Tenerife. The truth is you don’t have to go skiing or hiking to enjoy the beautiful vistas offered by many picturesque resorts or vibrant cities that have a colder climate. But you should also know how to dress appropriately and what to pack, so you came to the right place.

To layer or not to layer?

This is a tricky one and it depends on the weather and your type of activity:

  • If you’re hiking, the answer is definitely yes because once you get more warmed up, you’ll need to take some of your clothes off.
  • Same goes if you’re traveling to a country that has very a very small difference between the morning and afternoon temperatures. A swift-looking cardigan over your blouse or T-shirt can look amazing if you take off your parka.
  • The answer could be no if there’s a big difference between the morning and noon temperatures, at which point you probably need a warmer jacket over your shirt. That can be fitted with multiple outfits, dresses, blouses and jackets alike, and it will also look pretty stylish.

What shoes should you wear?

We can tell you this much: no sneakers or sports shoes. It can really be tempting to wear sneakers because they’re so comfortable, but they’re definitely out of the question for a slippery terrain. They can’t handle the wind well either. And the sports shoes don’t look that cool except when you’re out in the wild or when you’re doing, you know, sports.

So get a cool-looking pair of boots, there are plenty of those. The advantages are many starting with them being:

  • Sturdy for constant use.
  • Waterproof, so they can handle their snow.
  • Manufactured with a thicker sole, so they’ll keep your feet cozy.

And the truth is that most winter boots for women nowadays aren’t bulky at all, most of them actually look incredibly cute. The only issue might be to take them out at the airport but get the right laces and that’ll be a piece of cake.

How to accessorize fashionably

There is such a thing as accessorizing in winter without freezing to death if you’re wearing some (or all) of the items below:

  • A hat.Depending on how warm it is outside, you can choose anything from a Fedora to a wool beanie or a bobble hat.
  • From stylish black leather that goes great with fancier trips in the city center to multi-colored wool that’s perfect for camping, you have a pretty wide pool choice here too.
  • A scarf.Whether you want something made from cotton or a warmer, knitted, handmade scarf, you should focus on getting the colors right.
  • A bag.Your bag can be made from leather or polyester, it can be handheld or a backpack, all this depends on the occasion and what you’re carrying. Just make sure you don’t fill your luggage with bags, you need a versatile one that goes with most of your plans.

What colors should you choose?

Getting the right outfit also entails choosing colors that are versatile, that can fit different situations and that go well with each other. So we advise you to get:

  • Blue jeans.
  • Vibrant colors and interesting patterns for the first layers, especially when it comes to tops and dresses.
  • Your leggings can have different, vibrant colors when they’re the only visible splash of color.
  • Earth-tones or beige nuances for your sweaters, boots, and jacket.
  • Vividly colored gloves, hat, scarf, and bag.

What can you actually wear?

Let’s discuss some cool outfits that you can wear at different times during your trip. For a week’s trip, you’ll need to pack:

  • One winter jacket that’s waterproof, windproof and doesn’t make you look like a fluffy marshmallow.
  • Two pairs of jeans, one that’s skinny jeans and one that’s boot cut.
  • Three or four pairs will do the trick but get different colors.
  • Five tops. Choose more intense colors for each.
  • Two sweaters, one that has a turtleneck and one with a lower cut.
  • Two cardigans. Choose cashmere or merino wool, you’ll love these.
  • A down vest.
  • Two warm, yet stylish dresses.
  • A pair of mid-calf high boots that you can wear while traveling and Chelsea boots in your luggage.
  • The accessories above.

You can combine these items easily, as they’re all pretty versatile. They also take up little space, which is great.

For sightseeing, which implies constant walking, you can wear:

  • Your skinny jeans.
  • A yellow top.
  • The turtleneck sweater.
  • Your down vest.
  • The mid-calf boots.
  • A wool beanie.
  • A backpack.
  • Open-finger mittens.

If you’re just walking to get lost on the city streets, but you’ll maybe stop at a restaurant to have dinner, you can wear:

  • Bootcut jeans.
  • A warm, red shirt.
  • A beige cardigan.
  • Your winter jacket.
  • A pair of mid-calf black boots.
  • A red, leather bag.
  • A brown fedora.
  • Leather gloves.

If you’re going for a short hike, you can also wear:

  • Brown wool leggings.
  • A blue T-shirt.
  • A yellow open-neck sweater.
  • A warm, knitted scarf.
  • A red bobble hat.
  • The down vest.
  • Your mid-calf boots.
  • A backpack.

If you’re going to a fancy outdoor ice rink, you still need to be as pretty as you can:

  • Black wool leggings.
  • A blue dress that’s short enough though.
  • A tan-brown turtle-neck sweater.
  • A yellow beanie.
  • You can wear your winter jacket to the skating ring.
  • Wool mittens.

If you go to an open-air concert or an outdoor festival, you’ll need to look stylish, though comfortable enough for more hours outside:

  • Skinny jeans.
  • A top that you like.
  • A long, brown turtle-neck sweater.
  • Your winter jacket.
  • A fedora hat.
  • The Chelsea boots.
  • A leather bag.
  • Red leather gloves.

What will you pack?

With that in mind, we’re curious where you’ll go and what you’ll pack. Which of our suggestions inspired you most and why? What else would you consider wearing? Don’t be shy and leave a comment below.

Author Bio:

Rebecca lives in USA, but loves hiking all over the world. Her favorite is Everest Base Camp Trek in Nepal. It usually takes 16 days, but she likes to slow down, enjoy mountains, company of other adventurers and take more pictures, so it took her 28 days last time. Another of her passion is the ocean, so all short and long hikes along the ocean shore bring a lot of joy. She also writes for