Great Travel Shoes: Cute & Comfortable Shoes for Traveling

best shoes for travel

I’ve said this before and I’ll say it again: why does it have to be so hard to find great travel shoes? Sure, there are well-made, comfortable outdoor shoes that hold up to rain, cobblestones, and hours upon hours of walking…but it seems they are only worn by Americans! Since few women in Brazil, Italy, or Japan would wear them, I look for a travel shoe that combines comfort and style.

To complicate matters, I have plantar fasciitis, which makes comfortable shoes for travel even more important. Finding cute and comfortable travel shoes is not easy.


Let’s break down the best travel shoes by type and see what we have:

1) Sandals for travel: Birks, Naot & Chacos

Many sandals don’t have sufficient support for the walking that comes with travel. To make matters worse, people who live anywhere that’s warm enough to wear sandals are probably used to seeing only flip-flops or cute, thin sandals, which are OK if you’re going to the beach but don’t suffice for days of travel.

Comfortable sandals for travel:

Birkenstocks are very comfortable for traveling, especially if you need a shoe with sole support. My favorite day-to-day sandals are these Giza Birkenstock sandals for travel and these more modern Birkenstocks, but make sure to break them in a bit before traveling. And good news: if you like the support and feel of Birkenstocks soles, you can get inserts to use in other shoes.

comfortable sandals for travel

Cute sandals for travel:

These Naot sandals are some of the most comfortable shoes I own! The soles, made of natural latex and cork, are designed to replicate the shape of your foot, so they almost instantly feel like something I’ve worn a million times, something that just feels right.

Beat Shoes for Travel | This Is My Happiness

Besides Naot shoes’ flexibility, durability, shock absorption, and arch support, the most important quality to me is the elevated footbed center, which releases pressure in the joints of the center of the foot. I believe that this is what makes my feet feel so great in these. I have plantar fasciitis in one foot but cannot tell when I’m wearing these.

Sturdy sandals for travel and hiking:

Another quality option is Chacos sandals for traveling. The good news is that they are amazingly comfortable and durable–I can walk all day in them with zero pain. And I’ve had mine for 10 years, and they’re still in excellent condition. They’re also adjustable, which is handy in case your feet need a little more room along the way.

The Quest for Great Travel Shoes

I love my Chacos for walking and hiking, but they’re bulky. Try their other styles of cute and supportive sandals, like these and these.


2) Slip-on shoes for travel

“Street shoes”

These slip-on street shoes from Everlane make a comfortable, easy shoe for travel, plus they’re all leather. TOMS makes a similar leather slip-on shoe.

Slip on shoes for travel

Mary Janes: an old favorite

Since my first pair of Mary Janes in high school (red satin ones from a Chinese store in Sacramento), I’ve loved the feminine look of the many pairs of Mary Janes I’ve owned. The good news is that there are comfortable Mary Janes, like these from Hush Puppies. I wear these Mary Janes for hours on end and never feel uncomfortable. They have plenty of arch support to make walking and standing for hours no problem.

The Quest for Great Travel Shoes

Very light and comfortable!

The bad news? Mary Janes are not appropriate for all types of weather because the top of your foot is exposed. Without being able to wear socks or have your whole foot covered, these shoes won’t work on cold or rainy days.

3) Boots for travel: Be sure to size up!

Boots are a wardrobe staple for me but are a mixed bag while traveling. The good news about boots is that they are great in rain and cold weather, and they can dress up an outfit. And if you shop carefully, they can be comfortable–I have found that boots a half size up are best because they don’t pinch and allow room for socks and/or inserts for extra cushioning. Try classic styles like these brown leather boots and these comfortable black boots.

The Quest for Great Travel Shoes

These Ellen Tracy boots and my black Franco Sarto boots are great for travel.

The bad news? Boots take up a lot of space. They can also pinch your feet after too much walking. When I wore my boots to work, they were great, but when I tried to walk around the cobblestone streets of Florence last year, they took on a life of their own and suddenly left me with blisters. I learned that boots for travel must be chosen very carefully.

4) Desert boots/low boots

Low boots seem to be popular right now, not just in the U.S., and I’ll admit that I’m a fan.

comfortable shoes for travel

Try Clark’s (see these cute desert boots). The good news for travel is that these can be worn with just about anything and are inconspicuous, but the bad news is that they do not stand up well to rain or cold weather. And they need to be broken in. For lots of walking, I need to go up a size and add good insoles.

5) Comfortable flats for travel:

Because I love a cute pair of flats with skinny pants, I am always on the lookout for flats that look good and are comfortable. I’m happy to say that I’ve finally found some comfortable flats from Hush Puppies. I can wear them on my feet all day at work  or for hours of walking.

Other recommended brands for comfortable flats include these: this honest Tieks review makes me want to splurge on a pair of these cute and comfortable flats. Or try these Dansko flats, these TOMS flats, these Born flats, and these Rockport flats.

6) Heels/Wedges for travel:

I normally try to use boots or a cute flat for dressing up while on the road. However, even though heels are not typically thought of as good travel shoes, there are some places and occasions that call for nice shoes. Comfortable heels have alluded me, but one lesson I’ve learned the hard way is that inexpensive heels are a waste of money — they need to be well made and have some support in the sole.

For travel, which includes more walking than you do at home, I would definitely avoid any heel with a strap across the top because it will eventually pinch. But I love wedges. The soles are light, and they’re multi-purpose: they look nice with pants, a skirt, or a dress. I tried these wedges from TOMS (also available on Amazon) but didn’t like them for travel–the front is too narrow and the heel too high for much walking.

7) Stylish sneakers for travel:

The variety in shoes these days is amazing. Check out how cute these stylish sneakers from TOMS are:

Stylish sneakers for travel

In the end, it comes down to a combination of shoes for every trip. Going to Italy in the fall? I would take my most comfortable high boots, desert boots, and Mary Janes or cozy flats. Going to Brazil? I’d pack Chacos for hiking, low boots for day outings, and nice wedges for evening, and I’d buy Havaianas when I get there.

Help me find better travel shoes! What are your favorite travel shoes and why? What kind of shoes do you wish you could find for travel?

I asked this question over on Facebook and got many answers from readers. Here are some of their picks for great travel shoes:

Clark’s (so comfortable!), Born (supportive and great quality!), Toms, Tieks flats (worth every penny!), Vasque lightweight hiking boots, Josef Siebel sneakers (totally European!), Keens (these had a few votes), Merrells (travel shoes for walking!), & Cole Haan’s weekender shoes.


Like this post? You might like these, too:

What to Pack for a Snow Vacation

What to Pack for Fall Travel

The Perfect Airplane Outfits

What to Pack for Summer Travel

What to Pack for Winter Travel

What to Pack for Brazil

8 Things I Never Travel Without

Top Tips for Packing + My Ultimate Packing List


  • Adriana says:

    Very fashionable. I am a one pair of shoes traveler. If I go to the mountains – one pair of hiking boots, hot weather – one pair of sandals, mixed wether – one pair of trek shoes. I must be the one European who is not in love with fashion lol.

    • Jenna says:

      I like your idea of one pair…this would simplify packing! And as you mention, some trek shoes can be worn in rain, too.

  • Carol says:

    As a Healthy Foot Practitioner™ I give a lot of thought to shoes. I love my Vibram Five Fingers. I didn’t think they would work for me but I am now up to 15 km a day in them on concrete sidewalks of Toronto. They are odd looking but the comfort won me over. Now that it is colder, I’m back in my Altra shoes. Both of these shoes are “zero drop” ie, the heel is no higher than the ball of the foot. Altra are more cushioned but nice and wide in the toe box.
    If you are doing a lot of walking in your travels, I’d suggest a zero drop shoe, either minimal or with cushion and support, as any kind of positive heel results in a chronically bent knee/hip and a posterior pelvis, compressed lumbar spine. Save the heels for dinner!
    Another option for Mary Janes are Soft Star shoes, which are pretty and roll up for packing.
    For a really great resource for shoe selection (not travel related, but this is about getting shoes that are best for your feet so it’s the same thing right?) read this blog post (with company links) from Biomechanics Scientist Katy Bowman:

    • Jenna says:

      Thanks for all the tips. My husband has those 5 finger shoes and the zero drop shoes. I haven’t felt the need for them but can see that taking good care of your feet, especially when walking a lot, is important, and that foot alignment is related to alignment of the whole body. Thanks for the insights…you’ve given me something to think about!

  • I had a pair of red campers sandals that saw me through a month of solo travel in Europe. Best travel shoes ever. I’m taking my keens to the Caribbean this winter for rainforest hiking and water activities and my Havianas for the beach!

  • Sycamore says:

    Check out the Fly London line–in particular the styles that begin with “Y” (Yala, Ylva, Yava, etc.). I have VERY fussy feet, and these are the only shoes I can wear all day. And I get compliments every time I wear them.

    They can be hard to find in stores, but several online retailers, including Amazon, carry them.

  • I have about four pairs of Easy Spirit Travel Time slip-on sneakers, fine with bare feet and great for getting through airport security fast. The best travel shoes, bar none, though are Blundstone boots from New Zealand. Originally made for working on 19th-century sheep stations. The slip-on ankle boots are a favorite of Toronto hipsters but I prefer the ones that are lower cut, like shoes. Completely smooth outside and in, no rubbing whatsoever, Slip on, weatherproof leather and wear like iron. I cannot recommend Blundstones enough for all types of terrain, city or country!
    Lesley Peterson recently posted..Montreal to New York City by train: Amtrak’s Adirondack routeMy Profile

    • Jenna says:

      I haven’t used either of these, so thank you for the tips. I will check out Blundstones now!

  • Alexandra says:

    I have foot problems, so for me there is no comfortable shoe except the highest end Asics runners. When traveling, I bring two pairs – the runners (in a colour, preferably – the current ones are bright pink and happen to be kinda in style) and the waterproof goretex ones. In the summer, the latter is substituted by birkenstocks, which i find i can wear with a skirt but only for a few hours. This makes me look totally out of style, and can only be combined with pants, and even then there are limits. I try not to look like an American because I am not one, and so speak loudly in an Italian accent. 🙂

  • What a quest! Packing shoes for travel is so tough–it’s always the thing I agonize about the most, because I like to get away with bringing as few shoes as possible. If you want to try a more comfortable and supportive flat, check out those from Dr. Scholls…I have a black pair with a cute buckle that I love, but you are right–don’t really work well in cold weather.
    Have you tried Danskos? Very comfortable, and so many styles to choose from, and the heel makes you feel more dressed up…also have a pair that are Dansko(ish) shoes by “Born” that I love even more because they don’t scream clog! Good luck!
    Kate @Wild Tales of… recently posted..Hike Henry W. Coe State Park: A Hoppin’ Good Time!My Profile

    • Jenna says:

      I haven’t tried either of your suggestions but will look into them. I need something more comfortable options.

  • Andi says:

    Summer I always go for gold sandals and winter I always go for black boots. On the plane I usually wear ballet flats.
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    • Jenna says:

      I like black boots in the winter, too. I’d love to know what kind of ballet flats you wear on the plane.

  • Leah says:

    During the summer, I always pack a pair of silver and gold sandals. In the winter it’s a pair of brown or black riding boots. I’ll bring both if it’s a long trip. For walking around, I’ll bring a pair of plain Adidas that remind me of the classic K-Swiss shoes. I’ll also take a pair of Toms. They’re surprisingly comfortable and easy to pack.
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    • Jenna says:

      I have thought about the plain Adidas because my son used to have a pair like that. Looking into them and the Toms as a comfortable walking shoe. Thanks, Leah!

  • For my 11-month trip around the world with my family, I was really happy with the shoes I took. Just before leaving I found a pair of Chacos clog-type shoes, with a covered front part and a heel strap. I wore them with black socks and long pants in the cold weather with no problem. They gave such great support that I didn’t feel my plantar fasciitis pain at all during the trip. And when they started to look really dingy by the end of our trip in Colombia, my crafty husband sliced off the toe covering to make them into a passable sandal.

    I also had a cute(ish) pair of short boots made by Arcopedico, which I loved for their lightness and flexibility. I did need to use an insert with them for long walking days. Arche makes a similar pair. Neither of these is cheap, but they held up very well!
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    • Jenna says:

      Good to know about the Chacos shoes. I didn’t know they made anything besides sandals. I also don’t know about the other brands you mentioned. Thanks for the tips!

  • My Keen sports sandals are my go-to shoe for traveling. However, I’m mostly headed to casual, tropical destinations. On our trip to Paris last summer, I’m afraid that I looked like the stereotypical tourist with my Merrell Sports Shoes, even if the above-ankle part of me was dressed nicely.
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    • Jenna says:

      🙂 Well, at least your feet felt good, and the Merrells are actually pretty nice looking, I think!

  • I wear Dansko clogs, Mary Janes AND sandals. They are a teacher’s best friend. They even make boots. I know they aren’t the most fashion forward shoes, but they sure are comfortable!

  • OMG, I can 100% relate. While travelling,shoes have been a massive pain in the arse.I generally wear pretty smart clothes while backpacking (collared shirts etc) and I never wear trainers at home. Finding a balance between a shoe you can do lots of walking in, that can survive monsoon seasons, and that look nice is virtually impossible 🙁
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    • Jenna says:

      Um, yeah, if you’re trying to survive monsoon season with your shoes, it would get complicated. I guess your best bet would be a not-too-big outdoor shoe with Goretex.

  • Cassie says:

    Jenna, great summary! I’ve struggled with this question for years. I’m looking for a good pair of low boots right now for this winter — I’ll have to swing by Old Navy! When traveling, I usually pack rugged hiking sneakers (if it’s an outdoorsy trip), stylish sneakers (pumas, etc.) for urban trips, and Tevas and/or flip flops for beachy trips, silver/fancy sandles for warm weater urban trips. My Crocs mary janes went to Paris with me this last time and I don’t feel they ever looked too out of place, but I wore them with jeans and I do tend to hang out in more ‘bohemian’ areas where shabbiness is standard — I rarely go anywhere that requires dressing up 🙂
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    • Jenna says:

      The Old Navy ones weren’t comfy when I first got them, but the more I wore them, the better they got. They’re what I wear for half-day outings on the weekends. Low boots seemed very popular in Italy when I was there last year, too.
      I’ve been eyeing those Crocs Mary Janes for a long time. Glad to know you liked them.

  • Dalene says:

    I love my Tieks (flats). Pricey, but absolutely worth it as I can walk for hours in them!
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    • Jenna says:

      I’ve heard only great things about Tieks (and they look beautiful, too!). Maybe something I should splurge on as an X-mas to myself.

  • I love love love my Merrell sandals! They’re strappy, not quite as athletic-shoe looking as the Chacos here, and so so comfortable. I’ve worn them with shorts, dress pants, and skirts. But I agree, finding cute, versatile travel shoes is very difficult. But when in doubt, I always go with Merrell.
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  • Cindy says:

    It depends on how much walking I’ll be doing and how warm it is. 🙂 If it’s warm, I take my Chacos or Keen sandals (the Keens are lighter). Last month, walking miles a day in England and Italy, I lived in New Balance walking shoes and Keen hiking shoes (for trails that were sometimes muddy). I don’t worry too much about fashion while traveling!

    • Jenna says:

      I like your Keen shoes. New Balance makes nice sneakers for kids, so I’ll have to check out ones for adults. I need a pair of shoes that would be super comfy for long walks while traveling.

  • Jennifer Wyatt says:

    I have troll feet and the shoes that work well for me are by Dansko. I also like Merrell if I want something a little more sporty. My foot doctor warned me against totally flat shoes like Keds.
    I have some Orthaheel boots that are fantastic and cute, too.

    • Jenna says:

      Yeah, totally flat shoes don’t work for me, either. That’s why I can’t wear Converse. I also get pain in the sole of my right foot (left over from pregnancy) when I wear shoes that are too flat or don’t have enough cushion.

  • I love Born clogs for three reasons:
    1) The thick soles make them super comfy for long walks.
    2) They come in cute styles with buckles, studs, cool stitching, and stamped designs.
    3) They’re easy to get off and on at the airport.

    • Jenna says:

      It sounds like you and Tami (who also left a comment) think the same way. Thanks for the tip, Glynnis!

  • Katie says:

    Oooh, I went through this when preparing for a 3-week trip to Europe last year. I ordered dozens of shoes (thank you Zappos for free shipping and return!) and finally ended up with black Ecco sneakers (called Chase Tie). They were comfortable right from the start and even with tons and tons of walking, they were always comfortable. I only wished they looked better with a skirt. I still wore them with my skirts and tried to pull of a sporty vibe, but I’m not sure how successful I was.

    I love getting all the tips from the comments and can’t wait to check some of these out for future trips.
    Katie recently posted..Unexpected Architecture in UtahMy Profile

    • Jenna says:

      That’s another one I’m not familiar with. I love that you tried so many (dozens?!) pairs and finally decided on those. Must be great shoes.

  • Aahhh, tough choices! I used to bring too many shoes, but learned the hard way to keep it simple and light. I do love boots on the road and because of their size I usually wear them on the plane. I have to say you’ve encouraged me to find nice low boots – I see them working well with both skinny and regular jeans. And heels – I always bring one pair for a night out. They’re definitely not for sightseeing. 🙂
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  • Allison says:

    I’m reading the comments with interest because I’ve had plantar fasciitis for over two years. I need plenty of cushion and arch support in every shoe I wear, and alas, no high heels. I have a pair of Dansko leather sandals that are comfortable all summer. I also like my Chaco sandals and Merrell shoes. I keep an eye out for brands that combine comfort with style because if I have to choose, comfort keeps me traveling.
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    • Jenna says:

      True. I have that same problem in my right foot (since my first pregnancy), but it acts up only sometimes. I have a small gel insert for the ball of the foot that helps a lot.

  • Kristen says:

    Try They have several styles that are attractive (can be dressed up/down) but with sporty bases for walking. I’ve gotten the most shoe compliments ever while wearing them. I traveled with mine to Cambodia this summer; they stood up great to walking & dusty roads.

  • i’m stuck – i can only wear dansko professionals, since my ankle surgery. i love all your choices!
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  • Love those mary janes! Yes, not practical in cold weather 🙁 I used to be a $150 for a pair of sandals girl. I discovered a pair of sandals that I LIVE in. I got them for €15 at Decathlon in Italy. I got three extra pair for when they finally blow out.
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  • Love this! It’s so important (and so hard!) to find great travel shoes. Pinning!
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  • Why is it so hard to find shoes that are comfortable AND cute??! The classic $3 Old Navy flip flops are still my go to but I’m sure my feet will pay the price of having zero support one day.
    The Roaming Coconuts recently posted..Our 13 Best, Worst, and Strange Travel Moments of 2013My Profile

  • Nisha says:

    I have 23 pairs of footwear… all kinds. But when it comes to travel I restrict myself to only 3 -4 of them depending on where and when I am going.

    Nice post.

    Will try to write a similar one on my blog as well. Before that I need to click pics of them. 🙂

  • Molly says:

    this article was certainly helpful, especially in re-assuring myself that it is okay to take more than 1 pair of shoes with me on vacation! I am going to China for a little over two weeks in May and have been trying to figure out what to bring. I work at a shoe store so I certainly have access to all of the information I need. As it will be hot while we are there I am bringing my Brooks, very supportive but light sneakers, Birkenstocks, g-r-e-a-t arch support and there are some cuter styles now (biggest downfall is most of them can’t get wet), my black canvas Toms, some arch support but mostly a nice light shoe for a hot day or to wear around the hotel, and my Toms wedges, these are the most comfortable heels I have found, they are about a 2 inch heel with some support and I can wear these all day, I love them. (I am a big Toms fan)

    • Jenna says:

      I have a pair of Toms wedges, and I love them except for the part that goes across the top of my foot. It cuts into my skin too much, making it hard for me to wear them all day. The sole of those shoes is amazing, though.

  • Joanne says:

    Birkenstocks! I’ve tried almost all of these brands and have never had more success with avoiding foot pain, Achilles pain, and foot fatigues as with Birkenstocks! They are have a fashion moment with lots of colors and styles so take advantage!

    • Jenna says:

      Yes! I love Birkenstocks and wear my Giza sandals all the time. I actually mention them somewhere on this blog as a favorite travel shoe, I think in my summer travel clothes post.

  • Taryn Nicole says:

    Love this post. Found it via Pinterest looking for comfy shoes for travel. My husband and I are Europe Bound in 2 weeks for our anniversary and I’m really struggling with finding a pair of shoes for the long walking tours we will be doing etc. Women really do have it hard. I am big on not looking like a tourist and try to have shoes that compliment my outfits but I am not willing to budge on comfort! Great suggestions and I am now on Amazon checking out these brands! Thanks!

    • Jenna says:

      Hi Taryn, It is hard to find the perfect one, but I have been using Birkenstocks and even the cute new styles of Crocs and Merrells more lately.

  • Yvonne says:

    I can vouch for those Naot sandals! I can wear them all day walking and still have energized feet when I get home.

    • Jenna says:

      That is so good to hear! I love mine but my feet actually prefer the firmer support of Birkenstocks.

  • Natalie says:

    I find shoes are the most important thing you bring after a passport and money! If your feet hurt you will NOT enjoy the trip!! We usually bring low hikers and dress casually because we walk a LOT!! But, if I need to be dressier with dress pants I like to bring a Finn leather shoes. They are nice looking and really comfortable.

    We make sure the kids have comfortable shoes, too – even ONE person in your travel party who has ouchy feet will ruin the day for all!! Good socks – we like smart wool, are really important, too. Planning for good shoes and socks really pay off in the long run!
    Natalie recently posted..Tips for Wyoming visit with KIDSMy Profile

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