When buying the best women’s travel shoes and boots for upcoming fall and winter vacations, I am unswayed by the latest trends. After all, choosing which shoes to pack for travel is a little different from selecting shoes to wear to the office or for a night out back home. I might pick a pair of stylish, but uncomfortable heels to wear to that important client meeting– and swap them out immediately after the meeting is over. When planning a night out with friends in New York City, I factor in the venue and availability of taxis in neighborhood before deciding on the winning pair.
But just because some of my everyday shoes aren’t suitable for travel doesn’t mean I run out and buy so-called “travel shoes”– those ugly, orthopedic shoes with gummy soles that some “comfort shoe” company has marketed to desperate would-be travelers. Picking smart shoes for travel doesn’t have to mean looking in the comfort shoe section and giving up all fashion sense. You can easily find shoes and boots that are chic, stylish and just happen to also work for travel. As a bonus, these classic shoes and boots are attractive enough to be worn back home, even when you’re spending most of the day sitting at your desk instead of exploring a foreign city’s streets.
Our travel shoe-shopping tips are intended for the average vacationer, looking for some comfy but stylish shoes and boots for a typical city vacation (adventure-based vacations will require more specific shoes that we’ll cover in a later post). Here’s what I look for in fall/winter travel shoes and boots:
- The best women’s travel shoes and boots are comfortable. This is non-negotiable. Those shoes that are only good for a few hours wear should stay home. Exception: I allow myself one pair of sky-high heels just in case.
- The best travel shoes and boots are versatile. Travel shoes need to work with skirts and jeans, and be neutral enough to match multiple outfits.
- The best travel shoes and boots are flattering. I want to look my best when I’m vacation– that means I pass over the flats that make my legs look stumpy or the clunky shoes that make my feet look big.
- The best travel shoes are stylish, but classic. Finding travel shoes you can wear all day is hard enough. If I had to replace them every year to follow the latest trends I would go insane. Instead, I limit my travel shoe and boot wardrobe to classic looks that will work for several years.
- The best travel shoes and boots are well-made. While I can sometimes get away with a cheaper pair, the travel boots and shoes that I reach for again and again are higher-quality, and pricier than the average wear-around-town shoe.
- At least one pair of your travel shoes should be waterproof.
From boots to brogues to loafers and sneakers, here are the shoes and boots that have worked for my travels, whether exploring temples in Kyoto, Christmas markets in Germany, or shops and patisseries in Paris. All shoes are available at Zappos, my preferred online vendor for their free, no hassle shipping both ways and lenient return policy.
Quick Content Guide
- 1. Boots are Hands Down the Best Shoes for Cold Weather Travel
- Best Waterproof Suede Boots for Travel (La Canadienne or Aquatalia)
- 2. Best Women’s Travel Shoes– Comfortable Loafers
- 3. Best Women’s Brogues and Oxford Shoes for Travel
- 4. Best Women’s Travel Sneakers
1. Boots are Hands Down the Best Shoes for Cold Weather Travel
I always get excited each year when the weather gets nippy enough to finally pull on my boots. Unlike flimsy summer shoes, boots by definition give your ankles more support. Here are my top travel boot picks by type:
Knee-Length Riding Boots for Travel
Tall riding boots, even when completely flat, are incredibly flattering and make your legs look long. They also fully support your ankles, making them a great choice for all-day walking. Some boot-buying tips:
- For a sleek look, make sure the boots are fitted to your calf (it’s best to stick with boots that have a stretch panel with enough give to work with both skirts and over jeans).
- Show off slim ankles with boots that are nipped slightly at the ankle (or have an ankle strap).
I love the classic look of riding boots for chilly-weather travels. As a bonus, they add extra warmth to legs, which is great if you plan to be outside or long stretches of time (like exploring Christmas markets). The only downside is the extra room they take in your suitcase (I stuff my boots with socks and tee shirts to save on space).
Best travel riding boots for slim calves
I love these gorgeous Aquatalia black riding boots. Their boot shafts are cut on the slimmer side so they’re a great option for slender calves (and have an elastic panel for a precise fit). Boots usually look like golashes on my skinny calves so I’m always on the look out for slim styles.
Best travel riding boots for average calves
La Canadienne is one of my favorite brands for comfortable shoes and boots– like these beautiful black riding boots. These buckles though ensure a more custom fit.
For a less spendy option, consider these very affordable black leather Sam Edelman riding boots (available in five colors).
Best travel riding boots for wider calves
Sam Edelman has great riding boot options at every price point and different calf widths– perfect for travel or just lots of walking.
Best Over-the-Knee Boots for Travel
Over the knee boots have been hot for the last few seasons– they’ve been around long enough that they’re not just a passing trend but are here to stay. Over the knee boots are ideal for looking cute when you travel for a few reasons– most importantly, the longer the boot, the longer your legs look. But over the knee boots are also warmer than other boots, making them ideal to wear to cold winter climates (I could have seriously used these boots the sub-freezing Swedish Christmas markets). And when the weather is at that in between stage, when it’s iffy whether you need tights with a skirt, over the knee boots are the perfect transitional piece and will make your bare legs feel more covered up.
Although I always recommend investing in quality boots as you’ll keep them for years, I recently shopped for over the knee boots to wear out at night but didn’t have the budget to spring the for the Stuart Weitzman highland (if you do have the budget though, these boots are now on sale and so worth it!)
So I picked up less expensive version of the over the knee boot, made from microsuede, not actual suede. I bought the dark grey and found them more versatile than black (thought I later picked up the same pair in black too). The cheaper price means the boots aren’t very substantial which actually makes them perfect for a spare travel boot, as they are incredibly lightweight and practically roll up in your suitcase.
Best Moto Boots for Travel
Today you’ll find “moto boots” (also known as “biker boots”) in any department store shoe section. The chunkier sole is great for traction, and the overall casual look dresses down any outfit for day.
Left, these Cole Haan leather moto boots are stunners. Right, Frye’s engineer boots are the original moto boot– they’ll never go out of style.
These cute biker boot styles are more budget friendly. Left, by Ugg. Right, these are actually called “soft walk” boots so they sound perfect for travel.
Frye Boots for Travel
My Frye boots have been one of my best shoe investments– virtually indestructible, the buttery soft leather only get better with age. They have a million styles to choose from but I love the classic “Veronica slouch,” worn tall or slightly pushed down for a more casual look. While I consider Frye boots a classic staple rather than a fashion item, I was surprised when in Paris how many chic French women I caught sneaking a peek at my Fryes.
The only downside to Fryes is that they are pretty heavy. If you are hitting close to your weight limit you might want to wear them on the plane.
Best Waterproof Suede Boots for Travel (La Canadienne or Aquatalia)
Waterproof suede boots make awesome travel boots– they are soft, warm and perfect for hail storms or snowdrifts. Lighter and more chic than winter snow boots, you can take these boots through a snowstorm to a nice restaurant. (They are also great to wear to the office on snow days).
My Aquatalia boots are no longer available but I loved this similar Acquatalia waterproof pair.
For a dressier pair of waterproof suede, these are my own boots from La Candienne— even though they have a heel on them, it is mitigated by the built in platform, so the effective height is very walkable. As a bonus, they not only make a good travel boot, but they are dressy enough to wear to the office on a slushy day and still look perfect several years later.
Best Women’s Ankle Boots and Booties for travel
Flat or low-heeled ankle boots and booties
While you probably own these in black already, I found taupish-grey suede ankle boots to be incredibly versatile– they blended well with denim, cargo pants, leggings and tights. If you go a little cheaper on your ankle boots like I did, make sure to check the soles– mine were poorly made and slippery. Fortunately, your local shoe repair shop can put on rubber soles to fix any issues.
Another great option– these highly-rated Sam Edelman boots.
High-Heeled Ankle Boots for Travel– Just in Case
While I plan most of my travel shoe wardrobe for daytime walking, I do usually throw in one slightly inappropriate, “just in case” pair of heels. I was thankful to have my Sergio Rossie boots when invited last-minute to a fancy restaurant opening party in Vienna. I would also wear these out to dinner at night, especially if we were planning to take a taxi.
Best Sock Boots for Travel
This season I am reading that “sock boots” are the rage. I’ve been wearing this style boot forever because I like the way they make my ankles look slim. I don’t pay too much attention to trends as classic styles are always classic, but I was a little amused that these boots I’ve owned for years (and are still made) are now trendy
If you just can’t do stilettos, I can also recommend these super comfy (and slightly more practical, as they are also waterproof) La Canadienne boots (I have them in both black and grey– this style is similar). They also have a built in platform and stable block heel.
Best Hiking Boots for Travel
If you are going out on the trails, you already know you’ll need hiking boots. But if your hiking is limited to navigating cobblestones on your vacation, hiking boots are probably overkill. Unless they are these super cute vintage-look boots from Joie. I found these on the pages of this month’s Vogue and imagine they would look fabulous with tights and a mini. On my wish list.
2. Best Women’s Travel Shoes– Comfortable Loafers
3. Best Women’s Brogues and Oxford Shoes for Travel
These stylish oxfords are next on my travel shoe list.
4. Best Women’s Travel Sneakers
I already recommended these Superga sneakers in my best travel shoes for summer post. For a winter update, skip the bright white and pick a darker shade.
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What are your favorite travel shoes for fall and winter? Share in the comments below!