Cold feet on a trip will ruin your day faster than just about anything.
You can be standing in front of the most beautiful cathedral in Europe, surrounded by Christmas lights and the smell of mulled wine, and if your toes are frozen and your socks are soaking wet, you aren’t enjoying any of it.
This is exactly why the best shoes for cold weather travel matter so much.
I’ve been a full-time traveler since 2021 and shoes are the one thing I never cut corners on, especially when looking for the best shoes for fall and winter travel.
In this post I’m sharing 15 picks across five categories, plus exactly what to look for and how to test your shoes before you fly.
I recommend getting them at least four weeks before your trip so you actually have time to break them in. (this is super important!)
Here’s what you’ll learn today:
✅ What to look for in the best shoes for cold weather travel
✅ How to test your shoes properly before the trip so you avoid blisters and surprises on day one
✅ My top 15 picks across sneakers, ankle boots, tall boots, loafers, and snow boots
😩 If you’re already stressing about bulky coats and boots, answer 2 quick questions here and I’ll send you a custom carry-on packing list for your fall or winter trip.
Let’s get into the best shoes for cold weather travel!
This post contains affiliate links. If you make a purchase through one of these links, I may earn a small commission at no extra cost to you. Thanks so much for supporting my blog if you’re planning to shop! 💛 (if not, just enjoy the post)
Estimated reading time: 15 minutes
The best shoes for cold weather travel are leather sneakers for everyday walking, waterproof ankle boots for unpredictable weather, and one snow or heavy rain boot for serious conditions (if needed). Comfort, traction, and at least some water resistance matter more than anything else. Plan to buy them at least four weeks before your trip so you can break them in and test them properly.
What Makes The Best Shoes For Cold Weather Travel?
There’s no such thing as one perfect shoe for every trip. What works for five days in Paris in October isn’t the same as what you need for a week in Reykjavik in February. But every pair of travel shoes for cold weather travel should have five things in common, no matter the destination.
👉🏼 Some level of water resistance. Fall and winter mean rain. Drizzle in London, full storms in Amsterdam, wet snow in Munich. You don’t want soaking wet feet two hours into your first day.
👉🏼 Real traction. Wet cobblestones are no joke. Look for rubber soles with actual tread. Smooth leather soles look beautiful but they aren’t safe.
👉🏼 Warmth without bulk. A good cold weather travel shoe has insulation or thick enough construction to keep your feet warm without weighing five pounds.
👉🏼 All-day comfort. You’ll walk more than you think. Choose pairs you’ve actually worn for hours, not pairs that just look cute in photos.
👉🏼 A polished enough look. Europeans dress up. You don’t need stilettos but loud athletic shoes do stand out. Simple leather or suede reads more polished than bright running shoes. This depends on the city you’re visiting.
🎯 Also read: the 12 Christmas market outfits I packed with just 2 pairs of shoes
How to test your shoes before your trip:
Don’t skip this part (trust me).
✅ Wear them around the house for at least a week. Hardwood floors, stairs, sitting at your desk. Pressure points show up early.
✅ Take at least one long walk. Three miles minimum, five miles even better. Wear the same socks you plan to pack for the trip.
✅ Test on different surfaces. Sidewalks, stairs, tile, gravel. Heels slip more on smooth indoor floors than on outdoor pavement. You want to know in advance.
✅ Test the waterproofing if it matters. A light walk in real rain or a quick step in a shallow puddle is enough.
✅ Never pack brand new shoes. Break everything in at home first.
1️⃣ The Best Waterproof Sneakers for Cold Weather Travel
A great pair of waterproof or weather-sealed sneakers is the shoe you’ll wear most on a winter trip.
True waterproof shoes are less breathable and make your feet warm. That can be a great thing for cold weather, but they definitely won’t be shoes you’ll want to wear in summer.
- Vessi Soho Sneakers. These are the ones I travel with in winter. Full waterproofing in a comfortable and stylish sneaker. Pack these if you’ll deal with frequent rain in places like London, Amsterdam, or the Pacific Northwest. (Available in 4 colors)
- Sorel Ona Ave Waterproof Sneakers. A fun and more affordable option than the Vessi Sohos. It may not have the 10,000-step comfort of the Vessi sneakers, but it’s a great option when your itinerary doesn’t call for long days on your feet. (Comes in 6 great colors!)
- Quince Italian Leather Sneakers. These aren’t technically waterproof, but they’re my favorite shoes I own. Clean white leather, super comfortable, and polished enough to walk from a museum straight into a casual restaurant. Spray with leather protectant before you leave and they’ll handle light rain just fine.
😩 Quince’s white leather sneakers are sold out right now, but they’re still available in black (all sizes). Want white for a trip that may bring some rainy days? The Veja Campo is a white leather sneaker that comes with lots of different logo colors. Just spray it with a leather protector before you go.
🎯 For even more options, see my full post on the best walking shoes for Europe.
2️⃣ The Best Ankle Boots for Cold Weather Travel
Of all the best shoes for cold weather travel, ankle boots are the pair I’d pick if I could only bring one, because they work with jeans, dresses and trousers.
They look great with jeans during the day, dresses or trousers for dinner, and they take up significantly less space than tall boots.
For cold weather travel outfit options where rain is in the forecast, a waterproof ankle boot is versatile and functional.
- Blondo Alida Waterproof Bootie. A stylish suede ankle boot that comes in 4 colors. The side zip makes it easy to slip on and off at airport security. Make sure to wipe off any salt marks at the end of the day, since salt is harder on suede than rain is. (Blondo has many beautiful waterproof boot options)
- Ariat Wexford Waterproof Chelsea Boot. Waterproof leather with stretch panels on the ankles for easy pull-on style. The 3 color options come in standard and wide options. For a trendy look, pair them with cropped wide-leg pants.
- Quince Italian Leather Sock Bootie. This is the pair of boots I travel with on cold-weather trips. And like my favorite leather sneakers, these aren’t waterproof. I do my best to avoid rainy places, but I still treat these with water-repellent spray when traveling to a destination where rain is possible.
🧥 Packing for a fall or winter trip and worried about bulky layers and boots?
Answer 2 quick questions about your destination and dates and I’ll send you a custom carry-on only packing list for your cold weather trip. It includes:
✅ The exact number of tops, bottoms, layers & shoes to bring (no overpacking)
✅ Outfit examples for chilly days, cozy dinners & travel days
✅ A short “don’t pack” list so you don’t waste space on things you’ll never wear
Tap your trip length below to start the 2-question quiz and get your fall and winter packing list in seconds:
3️⃣ The Best Tall and Mid-Calf Boots for Cold Weather Travel
Tall boots are gorgeous for fall and winter travel outfit options. They look elegant with skirts, polished with skinny jeans, and they keep your legs warm in a way no other shoe can.
The catch? They take up real space in a suitcase, which means they’re an optional addition to your list of the best shoes for cold weather travel rather than a “must”.
⚠️ A note for carry-on travelers: Tall boots are usually a hard no for carry-on only, unless you wear them on the plane. They make great shoes for traveling to cold and wet destinations when you have the suitcase space.
- Sam Edelman Penny Knee-High Boot. A clean riding boot shape in soft leather, pulls on easily, works with everything from jeans to a midi dress. Not waterproof, so spray with protectant if you want them handling unexpected weather. It comes in medium and wide.
- VIVAIA Filipa Knee-High Boot. Has a stretchy knit shaft and a grippy anti-slip sole for long sightseeing days. The upper is water repellent, not waterproof, so it’s great for drizzle but not for heavy slush. You can pick from 4 color options.
- Blondo Waterproof Knee-High Boot. Blondo is best known for waterproof boots, and their knee-highs come in several style options.
4️⃣ The Best Loafers and Flats for Cold Weather Travel
For dinners out, theatre nights, or just feeling a bit dressier on your trip, you might want loafers or flats in the mix. They elevate your winter travel outfit instantly and pack flat in a way many other dress shoes can’t.
Even though these suggestions are very comfortable, it’s especially important to break them in with enough time. Loafers and flats can be tricky.
Also, this style of shoe isn’t the best option when expecting wet or slushy walks around town.
- Quince Italian Leather Loafer. The affordable answer to designer fall loafers that cost five times more. Classic shape, real leather, pairs with trousers or jeans and a long coat. Add warm tights and they’ll take you from fall into mild winter. (these are the loafers I travel with this time of the year)
- Vionic Uptown Hybrid Penny Loafer. A penny loafer on a cushioned sneaker sole, from a brand known for comfort and arch support. It comes in medium and wide widths and lots of colors.
- More Quince flats are available in soft neutrals that work with everything in a winter capsule. Quince shoes typically run true to size and the brand has 365-day returns, so you can try a pair well before your trip.
🎯 Going on a river cruise? Here are the boots and dinner flats I’d pack for a Christmas market river cruise, plus all 14 outfits they go with.
5️⃣ The Best Snow and Heavy Rain Boots for Cold Weather Travel
For trips where snow is on the menu or you know you’ll be dealing with sustained rain, you need a real boot. Not water resistant. Fully waterproof, with serious traction.
These are the heaviest of the best shoes for cold weather travel, and the ones you only pack when the weather really calls for it.
- Hunter Original Rain Boot. Fully waterproof rubber, a shorter cut than the iconic tall version, pairs with jeans, leggings, or trousers. Pack these for trips with sustained rain or flooded sidewalks. (wear them with warm cashmere socks)
- Barbour Wilton Chelsea Rain Boot. Fully waterproof, Chelsea slip-on style with elastic side panels, and a more refined look than rubber rain boots. Pairs with jeans and a trench for a polished rainy day in Paris or London.
- Sorel Snow Angel Faux Fur Detail Waterproof Boot. Top pick when snow is a real possibility. Insulated, fully waterproof, built for ice and slush. Pack these for Iceland, Scandinavia, or any trip with accumulated snow on the forecast.
Quick Recap: My 15 Best Shoes for Cold Weather Travel
- Quince Italian Leather Sneakers. My favorite everyday sneaker. The white is sold out, but black is in stock.
- Vessi Soho Sneakers. Fully waterproof sneaker and the pair I travel with in winter.
- Sorel Ona Ave Waterproof Sneakers. A more affordable waterproof sneaker in 6 colors.
- Blondo Alida Waterproof Bootie. Waterproof suede bootie with a walkable block heel.
- Ariat Wexford Waterproof Chelsea Boot. Waterproof leather that pulls right on, in standard and wide.
- Quince Italian Leather Sock Bootie. The boots I travel with on cold-weather trips.
- Sam Edelman Penny Knee-High Boot. Classic leather riding boot in medium and wide calf.
- VIVAIA Filipa Knee-High Boot. Stretchy knit tall boot with a grippy sole.
- Blondo Waterproof Knee-High Boots. Waterproof tall boots in several styles.
- Quince Italian Leather Loafer. The loafers I travel with this time of the year.
- Vionic Uptown Hybrid Penny Loafer. A penny loafer on a cushioned sneaker sole.
- More Quince Flats. Soft neutral flats with 365-day returns.
- Hunter Rain Boots. The classic rubber rain boot for serious rain days.
- Barbour Wilton Chelsea Rain Boot. Waterproof Chelsea for rainy Paris or London days.
- Sorel Snow Angel Faux Fur Detail Waterproof Boot. The snow boot for trips with accumulated snow.
🎯 Also read: how I pair these shoes with my cute and comfortable winter outfits for Europe, from chilly to freezing.
>>> If heading to Italy in the fall, make sure to read whichever of these posts apply to your trip:
Italy in September | Italy in October | Italy in November (packing strategies are very different, so I organized each post by region)
And there you have it. My top picks for the best shoes for fall and winter travel (depending on the temperature of course).
Picking the best shoes for cold weather travel is honestly one of the biggest decisions for your trip. Cold feet, wet socks, blisters from boots you didn’t break in. Those things will ruin a day in any city, no matter how beautiful the views are.
Order your pairs early, test them properly at home, and pack two or three pairs, depending on the trip. I travel with two on most winter trips. Anything more than three and you’re wasting suitcase space.
Thanks for reading!
XO,
Aimara
>>> PS: If you’re already stressing about bulky coats and boots, answer 2 quick questions here and I’ll send you a custom carry-on packing list for your fall or winter trip.
About the author:
I’m Aimara, the founder of Ways of Style 🙋🏻♀️ I’ve been a full-time carry-on traveler since 2021, which means I’ve spent a lot of time figuring out exactly which shoes are worth packing and which aren’t. Cold weather travel is a real test for footwear, and I’ve learned the hard way which pairs hold up through European cobblestones, sudden rainstorms, and 20,000-step days.
I created Ways of Style to help women travel light, dress well, and skip the parts of packing that feel overwhelming. If you want help building the rest of your fall or winter trip wardrobe, stick around. I’m so happy you’re here 💙
MORE WINTER TRAVEL ARTICLES 👇🏼
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- Your winter vacation outfits made easy (best jackets for winter travel)
- Best shoes for NYC winter (and 28 outfits to wear them with)
- Europe winter outfits (and which shoes go with each)
- Best shoes for Paris in December (and 24 outfits to wear them with)
Cold Weather Travel Shoes FAQ
What are the best shoes for cold weather travel in Europe?
For Europe in fall and winter, the right mix is leather sneakers for everyday city walking, a waterproof ankle boot for unpredictable rain and slush, and one snow boot if your destination has serious winter weather. Two or three pairs is enough for most trips. Look for water resistance, real traction on wet cobblestones, and comfort for long sightseeing days.
Are waterproof shoes really necessary for fall and winter travel?
Yes, especially in European cities where rain is common from October through March. Even one heavy rain day can ruin non-waterproof leather, and wet socks will derail your sightseeing plans. Travel shoes for cold weather travel should have at least some water resistance even if you don’t expect rain on your specific dates.
How many pairs of shoes should I pack for cold weather travel?
I usually travel with two pairs, and three is my maximum, even carry-on only. Any more than that and you’re wasting space. Wear your bulkiest pair on the plane to save room in your suitcase. Smart packing for cold weather travel means choosing pairs that each cover a different purpose, not packing five backup options.
Are sneakers OK for shoes for Europe travel in winter?
Absolutely, as long as you choose the right kind. Leather sneakers or waterproof sneakers like the Sorel Ona Ave work beautifully for European cities. Bulky athletic running shoes are less versatile and harder to dress up for dinner.
What winter travel shoes work best for European cities?
A waterproof ankle boot like the Blondo Alida is a great pick for European cities in winter. It handles rain and wet sidewalks and still looks polished enough for dinner. The Ariat Wexford Chelsea boot is a close second if you’d rather skip zippers and just pull them on.
How do I choose the best shoes for fall and winter travel?
When picking travel shoes for cold weather travel, start with the weather forecast and your itinerary. Mostly cities means waterproof leather ankle boots and a polished sneaker. Mostly outdoor activities means a heavier waterproof boot. Always include one pair that handles rain. Test every pair at home for at least a week before you fly. The best shoes for travel always come down to fit, comfort, and weather readiness over style alone.
Should I bring snow boots if there is a chance of snow?
Only if there is a realistic chance of accumulated snow at your destination, like Iceland, northern Europe in deep winter, or alpine areas. For mild snow or slush in cities like London, Paris, or Rome in winter, a good waterproof ankle boot is enough. Your winter travel outfit can stay polished without bulky snow boots in those cases. They take up too much suitcase space to pack just in case. Smart winter travel packing means matching the boot to the actual forecast.
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