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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.

Striking a pose on the famous Bow Bridge for Instagram in my over the knee boots.

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

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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.

Update: I still wear my Frye Veronica boots all the time– including a yesterday for a trek through Central Park for leaf peeping! And thanks to the reader who commented below that she also loves her Veronica boots.

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

If you don’t have a great pair of black ankle boots, an upcoming trip is a great reason to invest in a solid pair for travel. Ankle booties are so versatile for travel– they go great with leggings, tights and jeans.

Wearing ankle booties with my mom in Paris (she looks adorable sporting sneakers at age 67!)

Leaf peeping in Central Park with my all purpose ankle boots.

Mephisto nubuck ankle boots.  Mephisto is a big reader favorite because their shoes are incredibly well made, waterproof and and supremely comfortable.  I love the grey the cute fringe on these ankle boots (also in black and other colors). The slim opening is perfect for making the ankle look slender, and that tread ensure you won’t slip on icy winter streets.

 

I used to wear clogs. A lot. These ankle boots give you the cute look of clogs with the durability of a boot that won’t slip off your foot. I’m torn between the leather and suede versions Dansko boots

 

These best seller boots (#1 in comfort boots) are perfect to wear with just about anything. I love the taupe color (also available in black) and am ordering these for my next trip to Europe in December.

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 Heeled Boots for Travel: La Canadienne

If you’re tired of wearing flats and want some oomph for a day out and the instant leg lengthening heels can add, I found the perfect boot for you. Year after year, La Candienne comes out with a version of these boots– the key is the buit in platform, which lessens the steepness of the heel. And the absolute cushiness of the soles. If there is such a thing as comfort heels, these are it. I can and have walked around all day in them. Personally, I couldn’t spend a week in them nonstop straight, but they are great for mixing it up.

Want to look longer-legged? Heeled boots will do it.

I love that these La Canadienne boots are flexible– the sole is sturdy and cushy comfortable but also easily bends.

sock boots travel comfy ankle black

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. For light hiking I love classic styles over the sneaker style clunky hiking boots.

 

 

I adore these hiking boots, perfect for travel and on my Christmas wish list

 

These adorable boots from outfitter Columbia are chic and well made.

For a splurge option, I adore these Mephisto hiking boots, perfect for travel at home and abroad. Mephisto is known for their high quality footwear and a favorite among my readers, I just haven’t had a chance just yet to get a pair and review them.

These adorably named “boyfriend boots” from Northface are the bargain pick of the bunch.

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.  Left, these mock croc loafers from Ara. Center, these sturdy walking loafer from Clark, available in a range of spot on colors.  Right, another cute best-selling pair of loafers from Clarks.

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

best travel shoes comfortable chic cute fall women's

My Cole Haan Oxfords.

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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.

 

 

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.

But my new favorites are these adorable and even more comfortable adidas sneakers (thanks to the reader who recommended I try them). These adidas sneakers are not only all day comfy, but they also look great with jeans, leggings, a dress– you name it. For proof, see my pics below.

I wear these classic Adidas sneakers all the time (as you can see by all the photos above!)

If you need more support, these Mephisto sneakers are very popular and are recommended by readers.

 

If you need more support, these Mephisto sneakers are very popular with my readers and pass muster for stylishly blending in. They come in a bunch of colors but I like the black nubuck best.

 

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What are your favorite travel shoes for fall and winter? Share in the comments below!

30 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!

    Sally

  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.

  15. mandymanson 06/07/2017 at 9:16 am #

    Those Sergio Rosso boots would look so good with my Von Baer Business City Leather Laptop Bag for work.(a bit off topic but) I love quality leather of the bag and it has all the compartments I need.

    • Kristin Francis 10/24/2017 at 8:30 pm #

      Haha thanks for commenting! I’m hoping to do a bag post soon!

  16. Anonymous 07/18/2017 at 8:32 pm #

    After reading this, I bought a pair of Frye Veronica boots for a three week British Isles cruise from the end of May to mid June. I wore them almost every day! They were perfect for the soggy climate and looked great. I received a few compliments on them and I know people on the excursions were jealous of my footwear when the rain came in on us. They were the perfect “go to” choice and the low heel was much more comfortable as well. We did a stopover in Iceland – perfect terrain for the boots as well. Thank you so much for the recommendation – I otherwise wouldn’t have heard about them. Now I’m thinking of getting a pair in another color.

    • Kristin Francis 10/24/2017 at 7:02 pm #

      Yay! Thanks so much for taking the time to write in, I LOVE hearing this! I am super picky about my recommendations so I am thrilled when others agree. I’ve had mine for years now, they never go out of style and they only look better with wear. I am also thinking it’s time for another color! Thanks again 🙂

  17. Robin S 07/27/2017 at 4:26 pm #

    I, too, LOVE Frye boots. The ones with the letter bottoms are the most comfy, and have spoiled me – I can’t wear any boot or higher-heeled shoe without leather soles.
    However, as a gal who grew up skiing, my calves and ankles don’t seem to like any style of pull-on boot. And Fryes are notoriously hard to get on until broken in. So, I recommend any Frye with a zipper. Some styles even come with and elastic gore (panel) that runs up the shaft, and I feel these provide the best support and comfort of any boot… ever 😉

    • Kristin Francis 10/24/2017 at 6:57 pm #

      Good to know re: zipper. As someone with skinny calves but a high instep, I find them a little harder to get on because they are stiffer– but the support is so good it’s totally worth it. I need to check out the new styles and update, but I still wear my Veronica slouch boots year after year.

  18. Robin Shudak 07/27/2017 at 4:29 pm #

    I have Wellies from commuting in DC. But, yes, they are too bulky for travel. However — in I’m a quandary: I’m going to Scotland during its ‘rainy season.’ So I’m thinking about Chelsea Wellies. Have you ever tried them?

    • Kristin Francis 10/24/2017 at 6:55 pm #

      Robin, I haven’t tried Chelsea wellies– but they look interesting! Maybe I’ll check out a pair. Did you already go to Scotland?

  19. Robin Shudak 07/27/2017 at 4:29 pm #

    Ugh LEATHER bottoms! Stupid autocorrect!

  20. Tina 01/19/2018 at 9:28 am #

    Found your page on Pinterest and I LOVE these suggestions! I do have a question though. The photo in the link shows a pair of black hiking boots with red laces. Do you know what pair that is? I’m having the HARDEST time finding simple ankle height boots for hiking/backpacking but that can also be worn out (saving space!). Would love to hear from you!

    • Kristin Francis 01/19/2018 at 11:23 am #

      Hi Tina! Thanks so much for the kind words! The post you came across is 2014, which I updated and removed those boots (by Joie) bc they weren’t being made anymore. Also I have a NEW post I wrote this winter where I have a section on cute hiking boots– several brown with red laces which I find more versatile than black anyway. My friend wore hers on the streets of Paris on our last trip and looked super cute. Check out the newer post here: https://souvenirfinder.com/2017/11/06/best-winter-travel-shoes-sneakers-boots-reviewed-comfortable-stylish-cute/

      • Tina 01/19/2018 at 12:51 pm #

        Thanks! I agree, brown is best but I’m still having a hard time finding something that can pass as casual wear too haha. I like to limit my packing. I’ve seen the other pairs mentioned and they aren’t exactly what I’m looking for. I like the Darren Mountain Light Cascade boots but the ankle is a bit low for my liking and I’d prefer to pay half that price. Merrell has the “sugarbush” pair which are cute but I don’t like the two tone brown. My hunt continues!

        Luckily I have strong ankles so really just need something comfortable and with a solid grip for steep inclines or descent.

      • Kristin Francis 01/26/2018 at 1:05 pm #

        yea not a fan of two tone. Lmk if you find anything cute!

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