3 Favorite Women's Winter Travel Shoes

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Winter packing always has me considering how I can repurpose and bring down weight. Winter clothing just tends to be more bulky, so I want to minimize however possible, including with winter trip shoes!

Here are my favorite 3 shoes to pack for a winter trip. I love that they’re versatile for a variety of events and activities and weather scenarios, while still being super comfortable – my number one priority when traveling (all that walking!).

White Sneakers

I’ve mentioned my beloved white sneakers about 9,000 times because they’re the best. Comfy for lots of walking through cities and do fine on paved paths or gentle trails if you’re exploring outdoors.

Pros: I’ve worn them in light rain and they’ve been 100% fine and kept my feet dry. They’re easy to wear with a wide variety of outfits from jeans to nicer pants to skirts/dresses, and are comfy with tights or socks. They’re also quite lightweight (especially for a sneaker) and I’ve successfully washed them in the washing machine.

Cons: I wouldn’t choose them if I knew there was going to be a lot of rain and I was going to spend a lot of time outside. And because they’re lower on the ankle, they’re also not the best for muddy paths. They’re also harder to dress up for nicer events.

Black Leather Lug Sole Chelsea Boots

I searched long and hard for a pair of boots that I was confident would be long-lasting, look cute with a lot of outfits, fairly waterproof, and didn’t look too “heavy” on bottom. These were the winners!

Pros: I love that they have a translucent lug sole instead of a black one, which helps them feel lighter on the bottom. I’ve worn them for hours walking around and they’re SO comfortable and sturdy and keep my feet bone dry. Look great with jeans, pants, skirts, and it’s easy to include a warm insert for colder weather, and perform well in all sorts of weather conditions. I’ve worn them tromping through wet mud and they cleaned up perfectly.

Cons: Also trickier to dress up for nicer events. They’re also fairly heavy, so difficult to carry around if you’re not wearing them.

Brown Leather Ankle Boots

These are the dressiest of the lot so are a good option if you know you’ll have a nicer event or two, but still work for casual outfits. Mine are old from here but here’s a similar pair that I think looks even nicer and even more comfortable.

Pros: Lovely shape and construction that works well with nicer pants and skirts, while still very functional with jeans. They do perform well in different weather scenarios!

Cons: Generally not quite as comfortable (or warm) right from the get go, or for walking for hours on end. Mine took a little while to break in before they were totally great. I recommend comfy inserts if you know you’ll be doing lots of walking!

Which ONE Pair of Shoes for Winter Travel Should I Take?

If I were only taking one pair of shoes for a winter trip (which I do many times), I’d for sure go with the black Chelsea boots. They feel the most versatile for indoor and outdoor and city walking, hiking, rain/snow, you name it. They’re also wildly comfortable and keep my feet warm, especially when I add in an insert. (I have a less warm one for daily wear and then these for when it gets super cold.)

What shoes do you usually pack when traveling in winter? I’d love to hear your go-tos!