Walking Shoes

I spent a lot of time walking around this week. One of the questions I get most frequently via email and Tumblr is what shoes to wear when traveling. A caveat a lot of people throw in is that they don’t want to look like a tourist. Here’s my thing about that… if you’re a tourist, nine out of ten times you’re going to look like one whether you like it or not! In my opinion, you might as well be comfortable!
Having grown up in Florida and gone to school in Washington, DC, I can spot a tourist from a mile away! There is a standard uniform that tourists don and a lot of young women (from what I can tell) choose things to “blend in.” But, they also look extremely uncomfortable. Touring cities requires a lot of walking. Even though those sandals look super cute with your outfit, getting blisters three hours in to a multi-day vacation is not fun. 
You also don’t have to give up all cuteness to be comfortable while touring. Here are some shoes that can put some pep (prep?) in your step.
Keds | These classic canvas tennis shoes look great with jeans, shorts, and even dresses! Treat them as you would a pair of ballet flats when creating your outfit. I’m seriously in love with the Keds for Madewell sneaks. They’re too cute with those polka dots. Madewell also carries the plain red, navy, or white versions. They’re lightweight so you can pack a few colors to mix and match throughout your trip.
Nike Sneakers | Desperate times call for desperate measures. If you’re traveling someplace with crazy terrain (or even just a concrete jungle), regular athletic shoes are the way to go. Typically, I avoid wearing running shoes unless I’m wearing workout clothes, but when I’m traveling, they’re really the best option. No back pain and definitely no feet pain! (They’re probably not the most convenient for going through airport security though!) Pack a bright colored pair and rock ’em.
Sperry Top-Sider | A great option whether you’re traveling or not, boat shoes are very comfortable. I suggest breaking them in a bit before wearing them on a trip. The greatest thing about Sperrys is that you can even slip in a insert to make the shoe even more comfortable. Dr. Scholl’s makes inserts designed specifically for women’s feet. I love the regular boat shoe. But… I’ve recently been loving the woven version. How beautiful!
TOMS | When I was just traveling, I wore my TOMS the entire trip! I used to hate them. I thought they looked so weird, but over time they ended up growing on me. Now, of course, I think they’re the most comfortable shoes out there. Green, navy, and red are good all-around options for traveling. They go with just about everything!!!
What shoes do you wear when you travel?

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I ended up buying a pair of (overly priced) Nike sneakers in Rome this past summer because my feet were killing me! I definitely recommend them for touring a city. I wore Sperrys first and my feet were fine after a few days, but they soon became really sore.


Thanks for sharing your travel shoes with us!
The funny thing is that I actually have a pair of everything on your list 🙂

I don't travel a lot but whenever I do, my go-to shoes are typically my Toms. They're easy to slip into and super comfy even after hours of walking. I also really love that for every pair bought, a pair is given to a needy person! That definitely makes my steps a little bit lighter and bouncier!
I absolutely LOVE the way Sperrys look. They add a fun nautical air to every outfit and are great paired with pretty much everything. The only thing is that my Sperrys are uncomfortable for some strange reason. Even though I've worn them a bunch, they never fail to give me blisters on my heels after just a day of wearing them. I'm convinced that my feet are freakishly shaped or something!

**NOTE: If anyone has advice for making Sperrys more comfy or constantly gets blisters with them, PLEASE PLEASE PLEASE contact me in some way. I love them but they kill my feet 🙁

Keds are such adorable sneakers and like you said, the ones for Madewell are super cute! They definitely work with everything. My only concern with Keds is that they don't seem to provide very much support. Is wearing them a lot bad for your feet? Oh the questions that plague me…

Last but not least, Nike sneakers are amazing.
Though they may not be the cutest shoes around, they are like clouds of comfort hugging your feet. When you walk in them, your feet sigh a little bit and relax.
They are amazing (but as you say, are a little difficult getting through airport security with!).

Have an awesome day Carly (and everyone else who sees this comment)! 🙂



You could use shoe horns to break in your Sperrys and wear them around the house every day with an extra pair of thick socks to help stretch them out before you travel. Good luck!

Portuguese Prepster

I have a few pairs of TB flats that I've broken in so much they make great traveling shoes all year long! I also love my Toms that I've worn all Summer for my volunteering job, they are very comfortable and of course so are sperrys! I wore them with my uniform for years!

Bailey Humphrey

I do not own Keds, but I have a pair of shoes from Target that look the same. They are pretty comfortable. I love my Nike free runs. I like the style but sometimes (it might just be me because I have always had feet problems) they are not the most comfortable things. I wore mine in Carowinds, I went with a church camp, we were there for about 6 or 7 hours and my feet were killing me. I think that had to do with the amount of time we were on our feet. I am wearing my Nike's to Switzerland because I just know we will be walking and they do have great support. (Sorry if that was major confusing)For some odd reason, Sperry's unfortunately do not fit my feet and I was so excited when I got a pair for Christmas. Last Summer, my family and I took a trip to San Francisco and I wore my navy blue toms. They were great! We walked some then we would ride a bus/cab so I wasn't constantly on my feet. Overall, they were pretty amazing!

Have a great day!


I have a pair of Toms that I love, but I absolutely love my Sperry's! They didn't take long to break in, but they have always been comfortable. I make sure I wear thin, skin-colored socks inside to not ruin them. I have flat feet so it's important to make sure the shoes have arch support (Dr. Scholl's hurt after a while), so Sperry's have been the best. I'm thinking about getting a new pair for the school year!

By the way I came across this blog yesterday and I am in love with it! Keep posting!


I absolutely love waring TOMS when I travel! I usually wear ballet flats, but when I traveled to DC this past Spring Break wearing my TOMS, I never looked back! They are not only comfortable, but they're convenient to wear especially if you're going through TSA inspection.

I didn't even have to break them in! I highly suggest inserting insoles that absorb sweat or wearing low-cut socks (I prefer the former) when you wear them!


oh god! what an issue! My feet are completly sensitive! I've got my self a pair of these nikes too, but i rather die than beeing seen wearing them because they simply don't go with my not training clothes.
I totally stay with the TOMS, they have the tourist soul and mood simplified i guess, they say you are on vacation sweetie, act like it! So light.




I, too, don't like to wear running shoes unless I am wearing workout clothes, but I bite the bullet and wear them (my faves are a pair of cute, slim, grey & hot pink New Balance) if I am going to be doing serious walking.

My absolute favorite shoes for a day trip (shopping, tourist-y stuff, 4th of July…) are the Taos sandals I got last spring. They are cuter than tennies but supportive and very, very comfortable.

Mary Churay

I either stick with TOMS or with my Chacos. I know Chacos aren't the cutest things in the world, they're sandals made for hiking in, so they're VERY comfortable. Many of my friends have studied abroad and those have been their go-to shoe for the cobbled streets in Europe.


I still have yet to find a pair of TOMS that fit me right. I have three pairs of Sperrys, but the canvas ones bother me. My worn in Sperrys are my favorite to wear because they are so comfy, but the new ones are good too if I have to look nice. Critter flip flops from J Crew are also really comfy! I think they only sell them at the outlet stores now though.

Books, Beauty, and Bars on a Budget

I know a bunch of people have already said they don't recommend Sperrys for traveling, but they are always my go-to! I absolutely refuse to wear running shoes unless I'm working out and Sperrys have definitely proven to be the most comfortable travel shoe. Also, Sperrys are popular everywhere and if you are trying not to look like a tourist, Sperrys are absolutely the way to go. Running shoes SCREAM tourist.


Toms and Sperrys are both my go to's! I also sometimes just buy cheap ballet flats from Urban Outfitters and put insoles in them once they're broken in!

Julia D.

These types of shoes are ones I wear regularly. They're all pretty much my "go-tos" because of the reasons you mentioned. Definitely great options for traveling.

Massager Zone

I think my favorite shoe is the Nike sneaker considering the amount of walking I do on a daily basis. I disagree about the Toms. I absolutely hate them for personal reasons.