Great Travel Shoes: The Quest Begins

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 of walking…but it seems they are only worn by Americans! No woman in Brazil, Italy, or Japan would wear them, so I look for a travel shoe that combines comfort and style. Let me tell you, it’s not easy (for women, that is. It seems like kids and men can get away with a pair of brown Keens and sleek sneakers).

6 Types of Great Travel Shoes

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

1) Mary Janes

Since my first pair of Mary Janes in high school (red satin ones from a Chinese store in Sacramento), I have 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:

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.

The Quest for Great Travel Shoes

Merrell Mary Janes–a supportive sole that allows for hours of walking

2) Boots

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 gel inserts for extra cushioning.

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 also are great at pinching 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.

3) 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. I have two pairs that I like and will take with me on trips.

The first one is a pair of desert  boots purchased for $40 in Brazil 12 years ago. Yes, I am still wearing them, and even though they are on their last leg, they look good with everything. If you can’t go to Brazil to buy some, try Clark’s, J. Crew, and Eddie Bauer. 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. For lots of walking, I need to add insoles.

The Quest for Great Travel Shoes

These desert boots from Brazil have been all over.

The second pair of low boots are from Old Navy. I know, I never thought a decent pair of shoes could come from Old Navy, but after seeing them mentioned on Hither & Thither, I decided to give them a try. They’re now my favorite weekend shoes for fall. The good news is that they dress up an otherwise boring outfit and can be worn with pants or a dress; they are also comfortable enough to be worn for a few hours out. The bad news is that these boots are not comfortable enough for an entire travel day of walking.

The Quest for Great Travel Shoes

Cute with ankle jeans or casual dress and tights on a cool day

4) Flats

Even though I wish I could gush about my cute pair of flats for travel, I have nothing to say because I have never owned a pair that I could use for that purpose. I find flats to be too thin in the sole to provide enough comfort, but because I love a cute pair of flats with skinny pants, I am on the lookout for ones that look good and are comfortable.

5) Sandals

Another tricky type of shoe because most 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.

The most comfortable sandals I know of are Chacos. The good news is that they are amazingly comfortable–I can walk all day in them and have even used them for running! They’re also adjustable, which is handy in case your feet need a little more room along the way. The bad news is that they’re not really cute…I wouldn’t wear them with shorts or a skirt because they’re a bit bulky for my short body (but I have a friend pulls off a brown pair with skirts and looks great in them).

The Quest for Great Travel Shoes

I’ve had my Chacos for 7 years and have worn them for endless hours of walking.

6) Heels

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 heels. 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. These Italian made heels from J. Crew are the best ones I own, but I’m still searching for a versatile pair of well made heels.

The Quest for Great Travel Shoes

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 if I had any). Going to Brazil? I’d pack Chacos for hiking, low boots for day outings, and heels 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?

And remember, until Dec. 1, I will donate $1 to UNICEF for every comment left on my blog, so please start commenting! 

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, Toms (good support!), Tieks flats (worth every penny!), Vasque hiking shoes (lightweight!), Josef Siebel sneakers (totally European!), Keens (these had a few votes), Merrells, & Cole Haan’s line with Nike soles

Like this post? You might like these, too:

What to Pack for Fall Travel

The Perfect Airplane Outfits

And join me on Pinterest and Instagram for more travel and design inspiration.


53 Responses to Great Travel Shoes: The Quest Begins

  1. Adriana 11/03/2013 at 2:22 pm #

    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 11/04/2013 at 4:36 pm #

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

  2. Carol 11/03/2013 at 2:34 pm #

    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 11/04/2013 at 4:38 pm #

      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!

  3. Bringingtravelhime 11/03/2013 at 4:54 pm #

    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!

    • Jenna 11/04/2013 at 4:39 pm #

      That’s the good thing about Keens–they are good for hiking and water.

  4. Sycamore 11/03/2013 at 7:25 pm #

    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.

    • Jenna 11/04/2013 at 4:39 pm #

      Thanks for the tip! I will check them out.

  5. Lesley Peterson 11/03/2013 at 8:39 pm #

    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 11/04/2013 at 4:40 pm #

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

  6. Alexandra 11/03/2013 at 11:24 pm #

    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. :)

    • Jenna 11/04/2013 at 4:41 pm #

      lol. And I like the idea of pink Asics.

  7. Kate @Wild Tales of... 11/04/2013 at 8:27 am #

    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 11/04/2013 at 4:41 pm #

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

  8. Andi 11/04/2013 at 3:04 pm #

    Summer I always go for gold sandals and winter I always go for black boots. On the plane I usually wear ballet flats.
    Andi recently posted..England & Scotland With Trafalgar: Day 1My Profile

    • Jenna 11/04/2013 at 4:43 pm #

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

  9. Leah 11/04/2013 at 4:35 pm #

    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.
    Leah recently posted..My {Wo}Manly Bucket List to Support #Movember & #ManlyMomentsMy Profile

    • Jenna 11/04/2013 at 4:44 pm #

      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!

  10. Paige Conner Totaro 11/04/2013 at 6:22 pm #

    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!
    Paige Conner Totaro recently posted..Hyatt opens in KurdistanMy Profile

    • Jenna 11/05/2013 at 5:08 pm #

      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!

  11. Michele {Malaysian Meanders} 11/04/2013 at 6:38 pm #

    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.
    Michele {Malaysian Meanders} recently posted..Little India Preps for DeepavaliMy Profile

    • Jenna 11/05/2013 at 5:10 pm #

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

  12. Tami-TeacherGoesBackToSchool 11/04/2013 at 6:43 pm #

    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!

    • Jenna 11/05/2013 at 5:10 pm #

      Another brand to look into. Thank you!

  13. David @ That Gay Backpacker 11/04/2013 at 7:09 pm #

    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 :(
    David @ That Gay Backpacker recently posted..Guanajuato. It’s just pretty, like.My Profile

    • Jenna 11/05/2013 at 5:14 pm #

      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.

  14. Cassie 11/04/2013 at 7:27 pm #

    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 :)
    Cassie recently posted..Day of the Dead in EcuadorMy Profile

    • Jenna 11/05/2013 at 5:16 pm #

      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.

  15. Dalene 11/04/2013 at 8:17 pm #

    I love my Tieks (flats). Pricey, but absolutely worth it as I can walk for hours in them!
    Dalene recently posted..Iconic ParisMy Profile

    • Jenna 11/05/2013 at 5:17 pm #

      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.

  16. Francesca (@WorkMomTravels) 11/05/2013 at 10:50 am #

    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.
    Francesca (@WorkMomTravels) recently posted..Grand Traverse Lighthouse photo essayMy Profile

    • Jenna 11/05/2013 at 5:18 pm #

      OK, I’m off to look for Merrell sandals. Thanks for the tip!

  17. Cindy 11/05/2013 at 1:24 pm #

    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 11/05/2013 at 5:20 pm #

      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.

  18. Jennifer Wyatt 11/05/2013 at 2:18 pm #

    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 11/05/2013 at 5:21 pm #

      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.

  19. Glynnis Campbell 11/05/2013 at 8:24 pm #

    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 11/06/2013 at 8:32 pm #

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

  20. Katie 11/06/2013 at 12:03 pm #

    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 11/06/2013 at 8:43 pm #

      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.

  21. Pola (@jettingaround) 11/08/2013 at 5:19 pm #

    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. :)
    Pola (@jettingaround) recently posted..Photo(s) of the Week: Fall in the Chicago Botanic GardenMy Profile

    • Jenna 11/10/2013 at 8:27 pm #

      Yes, I love my low boots with skinny jeans, usually folded up to show the top of the boot.

  22. Allison 11/11/2013 at 3:45 pm #

    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.
    Allison recently posted..7 Tips for visiting the San Diego ZooMy Profile

    • Jenna 11/12/2013 at 1:35 pm #

      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.

  23. Kristen 11/12/2013 at 8:33 am #

    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.

    • Jenna 11/12/2013 at 1:38 pm #

      Thanks for the tip!

  24. wanderingeducators 11/13/2013 at 2:11 pm #

    i’m stuck – i can only wear dansko professionals, since my ankle surgery. i love all your choices!
    wanderingeducators recently posted..Eight Cool Things to Do in DubaiMy Profile

  25. Laurel- Capturing la Vita 11/18/2013 at 11:41 am #

    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.
    Laurel- Capturing la Vita recently posted..Italian Memories, a Poppy, and a Transistor RadioMy Profile

    • Jenna 11/19/2013 at 10:08 pm #

      They look really comfy, and you can’t beat the price! thanks for sharing, Laurel.

  26. Colleen Lanin 12/08/2013 at 10:03 pm #

    Love this! It’s so important (and so hard!) to find great travel shoes. Pinning!
    Colleen Lanin recently posted..Travel with Children Book CRAZY Holiday Discount – 40% Off The Travel Mamas’ Guide!My Profile

  27. The Roaming Coconuts 12/30/2013 at 7:00 am #

    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

    • Jenna 12/30/2013 at 8:11 pm #

      It is so hard! I wish I could find one or two go-to shoes for all travel.

  28. Nisha 04/19/2014 at 9:01 pm #

    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. :-)

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