Best Women’s Travel Shoes and Boots, Fall/Winter Edition 2018

Looking for the best womens travel summer shoes? Check out our spring/summer post here!

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.

best women's boot for travel fall europe

I wear my riding boots to death and take them on all my cold-weather trips between October and March.

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.

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

best fashionable but comfortable boots black knee length for travel
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.

Or try these Cole Haan classic black riding boots.

discount riding boots
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

best riding boot wide calves for walking

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

best over the knee boot for walking

These Stuart Weitzman 5050 boots are a classic and a serious leg lengthener. Totally on my wish list.

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.

comfortable travel boots over knee black

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!)


best travel boots over the knee heels suede microsuede comfy dressy

Wearing my dark grey over the knee boots to a museum exhibit in New York.

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.

While they don’t make my exact boot anymore, I found a similar microsuede over the knee boot here. The heel is sturdier and slightly lower than mine which makes them easier to walk in.


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

best travel shoes for women

Frye boots visit the Old Royal Navy College in Greenwich, England.

frye veronica slouch boots travel best shoes

I’ve worn these Frye Veronica slouch boots for years– they only look better the more they age.

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)

best boots travel winter waterproof europe

My four-year old boots from Aquatalia are still in perfect condition, despite wading through slush piles and snowdrifts.

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).

best knee high boots travel riding winter warm comfortable

My Aquatalia boots are no longer available but I loved this similar Acquatalia waterproof pair.

best waterproof travel shoes europe fall winter

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

comfy boots for travel europe women shoes

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.


best gray boots ankle bootie travel

Another great option– these highly-rated Sam Edelman boots.

High-Heeled Ankle Boots for Travel– Just in Case

comfortable stilleto ankle boots

My Sergio Rosso boots were a huge splurge, but worth it for the comfort.

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.

One the left, these boots have a similar look. Or try these Cole Haan boots for half off.

Best Sock Boots for Travel

sock boots travel comfy ankle black

Who knew, my several year old “sock boots” are now in fashion.

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

womens cute hiking boots

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

best loafer for walking women

A great pair of comfortable, sturdy loafers is a must for both traveling and home. I love these loafers from Mephisto (left) and these cute brown suede loafers from La Canadienne (right),

Some more budget-friendly loafers that are still stylish and comfortable for walking and travel– left, these tassel loafers from Trotter.  Right, these mock croc loafers from Ara.

3. Best Women’s Brogues and Oxford Shoes for Travel

best travel shoes comfortable chic cute fall women's

My Cole Haan Oxfords.


My suede brogues were the perfect shoe to walk through the bamboo forests of Arashiyama, Japan– even while recovering from a sprained foot, the laces and arch support provided plenty of support.

womens walking shoes oxfords comfy comfortable

These stylish oxfords are next on my travel shoe list.

More of the best women’s oxfords and brogue shoe for travel: left, these shiny patent brogues from Earth, and right these sweet nubuck shoes.

4. Best Women’s Travel Sneakers

best women's sneakers for travel fall winter cool

My tried and true Supergas– I wear these to death in every season

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!

17 Responses to Best Women’s Travel Shoes and Boots, Fall/Winter Edition 2018

  1. Sue Slaght 10/25/2014 at 10:18 am #

    Kristin I have to say you have a much better selection of boots than I! Great idea about the boots for fall travel. We are headed to San Francisco in a few weeks and I plan to take your advice.

  2. dianaveggienextdoor 10/25/2014 at 6:23 pm #

    I already got the supergas you recommended. Now looks like I need to start loafer shopping 🙂

  3. henrikam2013 11/04/2014 at 8:01 am #

    Great ideas for boots, I’m ready to go shopping!

  4. Anonymous 01/28/2015 at 4:02 am #

    great ideas for shoes and boots . Your words are invaluable thanks !!

  5. Goldwave 02/10/2015 at 4:06 pm #

    Thanks for all of your great tips! I just wanted to share another great tip regarding boots. A shoe repair person or cobbler can alter the shaft of boots to make them fit your legs perfectly. I discovered this from a co-worker with very slender legs who told me she paid only $20 a pair to have her shoe cobbler do this. That seemed like a great deal to me but they were friends, so it might cost more for most people. The result is pretty amazing; it makes the boots look custom-made, and improves ankle support as well.

    This might be a good time to note that shoe cobblers/repairpeople can do all sorts of things to make shoes more comfortable or last longer. For example, my brother pronates badly, so he has metal taps put onto the toes and heels of his expensive boots. This keeps them from wearing down as fast and saves him from having to replace the entire soles of the boots. They can adjust the size, color, heel height; all sorts of things.

    Okay and I’ll add one more tip: Shoe stretching spray is just vinegar and water. 🙂

    • Kristin Francis 02/10/2015 at 8:21 pm #

      Thanks so much for your tips! I’ve read about people getting boots taken in but was wary of trying it– good to know it works. Even if it’s more, it’s totally worth it for a great fitting pair. I have a few pairs of boots I bought in London where they measure your calf and you pick up your boots a few days later and I absolutely love them. But I’d love to have more options here in the US.
      I completely agree re: a good cobbler– I’m so picky about the fit of my boots and shoes that when I find comfortable shoes that both look cute and work I want them to last forever. I get them reheeled/soled every year or two. I had no idea there even was stretching shoe spray!! Can’t wait to test it out on one uncomfortable pair of heels. : )

  6. Annette 09/01/2015 at 12:41 am #

    Hi Kristin! You and I could be shoe shopping buddies! You have great shoe taste! I love fashion! I am such an overpacker, I am going to try to not to go crazy this upcoming trip! ( yeah right) lol Leaving for Rome October 1, I was thinking more fall fashion, boots etc. Should I bring any sandals? Summer wear? First time in Europe ! We are also cruising for seven days trip ending in Rome for four days. Do you think the dress code fits the ship also? I tend to wear dresses, skirts a lot . Any specific advice for this time of year? I am def. wearing or packing my fryes. One of my faves! Thank you enjoyed your tips!

  7. Lindsay 10/24/2015 at 1:50 pm #

    Love them all! What is the style name of

    the Aquatalia brown suede riding boot?

  8. Sally 11/19/2015 at 2:32 pm #

    Hi Kristin! I just came across this article when I was searching for a new pair of boots. I’ve had my current Clarks pair for what seems like forever. I’ve even gotten them resoled. Unfortunately, the zipper broke a couple days ago and the cost of that repair is not worth it at this point. I am deciding between the Frye Veronica Slouch and the style with the zipper in the back. Have you ever compared either? I’m guessing they’d be the same in terms of comfort/footbed. I live in Boston and do a ton of walking around the city. These would be the boots I’d use to commute, run errands, and everything else. Also, if you have another suggestion, I’m all ears. Thanks!


  9. Kathryn 04/24/2016 at 12:58 am #

    I like it and always wearing while backpacking tour.

  10. Anonymous 06/04/2016 at 2:08 am #

    Thank you so much for your tips! My supergas are basically my every day shoes now but I’ve got an upcoming fall trip so the boot tips are going to be super useful for me. Thanks!

  11. suziemaus 08/18/2016 at 9:06 pm #

    Great tips. And. Oh. My. I’m not new to travel in Europe, but always overpack and am vowing not to do so this year. How many shoes/boots should I pack for Europe for the fall? 2 weeks. We are mostly visiting his family (up and down Germany and Austria). Will spend lots of time in the car. And not a HECK of a lot of city/cobblestone streets. (I know for sure of 2 of these days.) Hiking in the Alps for a few days, I have those hiking shoes covered (Merrills) Plan on buying a pair of Superga sneakers (snakeskin) and um…I have black riding boots, brown booties w/ a bit of a heel, but comfy. Is this enough? Packing just one dress. I think I can get away with the black riding boots and tights w/ that for a somewhat dressier evening? I’m such a heels girl, but…???

  12. Judy U. 12/29/2016 at 7:27 pm #

    Hello! Thank you for your tips! I would like to buy boots online but i’m wondering if I should get them in my size (the size i normally get when i’m buying ladies flats) or should I get it one size bigger when Im buying boots?

    • Kristin Francis 02/16/2017 at 1:44 am #

      I get my usual size or order two sizes and return one. But I also check the comments from others who bought boots and see what they say about fit– that’s why I love zappos, great user reviews and free returns (though my doormen hate me for all the packages).

  13. Charles W 03/04/2017 at 9:23 pm #

    Thank you for updating the articole, Kristin.

    I’d like to add some things, If you allow me, maybe they’ll help someone.

    If you’re unsure of your calfs and have trouble finding boots that perfectly fit, try the tall variation of the Chelsea boot.
    Chelseas are a kind of Jodspurs but have an elastic strip on the side, which makes the width of the shaft adjust to what the calf requires. But nowadays I’ve also seen them knee-length and people call them Chelsea boots too, so who am I to swim against the current? Zappos has a few pairs, and they don’t look half bad.

    I also noticed you didn’t mention Wellington boots in the waterproof part. I’ll admit it, I’m also not a fan of wellies, but they’ve been evolving in interesting ways, and I’ve seen a lot of women wearing a pair on rainy weather. Do cast an eye over them if you find the time, and let me know what you think, I’m really curious.

    • Kristin Francis 03/22/2017 at 12:35 pm #

      I have a pair of wellies and wear them on the streets of Manhattan on rainy days! But they are way to bulky for travel unfortunately.

  14. Charles W 03/24/2017 at 9:56 am #

    I know what you mean.

    You can take a look at the folding wellies from Redfoot, they don’t look half bad, and seem practical.

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