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Best walking shoes for traveling–31 cute pairs

Best walking shoes for traveling

A few weeks back, I polled you all on your favorite comfy walking shoes for traveling! Summer is a popular time for big trips, but shoulder seasons (like September and October, and again in April and May) are also perfect times to travel. Whether you’re planning a fun adventure abroad that involves a lot of mileage, a short trip or vacation, or just making a point to explore your own city more, one thing you definitely need are a comfy pair of walking shoes! I’m sharing my favorites below, but also lots of options added at the end that are approved by you all, too!

One tip: as always, before any trip, leave time for breaking-in your shoes and consider your destination before making your final choices! (I.E. will you be encountering slippery cobblestones and need traction? Do you need something that slips on and off? How much support? Open or closed toe?) You can find the best tips for breaking in your new shoes here.

Most of all, shoes for travel should be comfortable, durable, and versatile! (Easy off/on for airport security is an added plus!) You’ll find the best shoes of all the above below–from sneakers to loafers to sandals.

Best walking shoes for traveling in 2023-2024

Best walking shoes for traveling

Madewell Court Sneakers and Everlane Court Sneakers (both reviewed here!)

Court sneakers have a classic style but subtle tomboy look that can go with any athleisure or casual outfits you have in your luggage—from dresses to denim, sweats, leggings, bike shorts, and more. I can vouch that both the Madewell and Everlane pairs are great. They’re VERY comfortable and I’d say medium support. I wear these classic white sneakers year round and in all types of weather! If I were going to bring ONE pair of shoes on any trip, any time of year, it would be these. The best sneakers–really, the best shoes for travel in general–in my opinion.

They’re leather shoes, which makes them sturdy, naturally water-resistant, and easy to clean. (You can find specifics about cleaning white leather HERE.) I’d say both are true to size, so I take my normal size in both pairs, but Madewell says they’re slightly narrow and recommends going up half a size. You might want to consider that if you have wider feet. 

Travel outfit to Montana–links and try on here

Chelsea boots: Wearing these waterproof leather Blondo Hallie boots but I also highly recommend these water resistant leather Caslon Chelsea boots from Nordstrom (you can also find last year’s style on Nordstrom Rack!) These Cole Haans are another great option, also waterproof! I HIGHLY recommend a comfortable pair of waterproof booties if you’ll be traveling anywhere with chilly cold weather and rainy. Why? Because not only are waterproof Chelsea boots classic, stylish shoes, but traditional rubber rain boots are a pain to travel with, aren’t comfy to walk in, and not easy to dress up for dinner–but a great pair of Chelsea’s? Amazing! They’re super versatile to style–in fact, I’ve traveled before and the ONLY pair of shoes I’ve brought are Chelsea boots! Another perk: they never go out of style, so they’re a perfect pair to be a staple in your wardrobe for a long time!

Blondo Hallie Boots sold on Amazon and DSW!

Everlane day boots:

I’m so excited because they brought one of my all-time favorite pairs of heeled boots back this season, I might have to get a second pair! (They haven’t sold them in years!) If you’re looking for a pair of comfy boots with a heel–these are it! I wore these on a quick trip to Portugal (meaning, I carried on, so I couldn’t take that many shoes!) and I walked for miles on cobblestone streets, no problem. They are made of soft leather, a roomy square toe and have a low heel. (Note: I wouldn’t wear these in super rainy conditions, but otherwise, the ideal fall/spring/milder winter weather boot!) If you are looking for a slightly different style, there is also another Everlane pair called the City Boot that looks super cute too!

Sizing: I took my normal size!

Best walking shoes for traveling

Another perfect travel shoe: Rothy’s Cap-Toe Ballet Flats

My Rothy’s “The Square” flats are probably my most worn pair of ballet flats. I LOVE the way they look and they’re the most comfortable shoes as far as flats go. They come in several colors (though I think these Chanel-inspired cap-toes are the best and make every outfit look so stylish). You could easily stick 1-3 pairs in your luggage when traveling because they take up virtually no space! Though they’re not particularly supportive, I’ve had long days where I walked miles and miles in these anywhere from San Francisco to Paris, and I was comfortable all day. (You could also remove the insoles and add your own more supportive ones as long as they were thin!)

Another thing to love about these cap-toe ballet flats is the fact that they’re washable! They even dry pretty quickly. Rothy’s are also made from recycled plastic bottles and ocean plastic, so you can feel good about your purchase in multiple ways. (You can read more in this post about why I love Rothy’s and their mission.) The one downside is the bottoms of the flats can be slippery until you break them in, but you can also have a cobbler fix that for you!

Rothy’s Driving Moccasins

Rothy’s Driving Moccasins

If you’re worried about the grip issue but like the style of a Rothy’s shoe, “The Driver” moccasins are a great alternative and the perfect balance of a comfy but durable shoe. The rubber outsole has a raised texture to prevent any slippage, which makes them really functional especially for places that may have slippery cobblestones. I also think they’re very comfortable and make for cute walking shoes. I wouldn’t say these have a “break in” period (as they’re fabric, it’s not like they “break in” like leather would) but your feet may need some time to adjust to them. In fact, I wore them all around Napa and they were great!

Beyond the functionality, I love the style as an alternative to sneakers. The moccasins are preppy and chic, and you may find they’re easier to wear than lace-up shoes, strappy sandals, or whatever else you’ve got in your bag. This alone will probably have you reaching for these again and again no matter what kind of traveler you are or where you’re exploring! (“The Driver” also comes in over a dozen colors to fit your personal style.) Note: You can remove the insoles and add your own if you need more support!

Freda Salvador Eda | Best walking shoes for traveling

Freda Salvador Eda sneakers (Sold on Amazon, at Bloomingdales and Shopbop too!)

These are my investment sneakers, but I have worn them so much that I think my cost per is about 50 cents at this point. These are my warm weather sneakers–with the d’Orsay design, they’re like a sneaker-sandal-flat? I love that they have an elevated feminine style and they’re quick to slip on! The soft leather makes them so comfy and easy break-in.

They’re definitely more than I’d spend on a sneaker and I mulled over the purchase for about a year before finally pulling the trigger, but I’m so glad I did. They go great with dresses, jumpsuits, shorts, swimsuits—pretty much anything you can think of. (I should note I’d only recommend these on warmer climate destinations for summer travel because of the cut-out, and I would also avoid these in dirty conditions because the soft leather will get scuffed easier than, say, a sturdier leather like the court sneakers I highlighted above!)

Another reason they’re great travel shoes? They’re so easy to pack (again, the shape is more like a flat than a sneaker, so they take up very little room in a suitcase!) They’re pretty much the whole package when it comes to comfortable travel shoes for warm to hot weather travel. (I often even bring them on beach vacations!)

Make sure to read the reviews for sizing, because while I found them TTS, some of you who are usually 1/2 sizes felt differently!

Nisolo Huarache Sandals

Nisolo Huarache Sandals (Sold at DSW, Zappos, and Target!)

Whether I’m at home or abroad, I wear these ALL summer – they’re the best sandals. I love the classic throwback style and the woven construction makes them super breathable while providing the benefits of being a closed-toe. They’re breezy enough for the hottest days from Mexico to Mallorca. I love wearing them my go to summer outfits of dresses, shorts, and jeans. Another plus: they are flat and take up very little space in your bag for your next trip!

Important to note that my pair is many years old. The color I got was raw leather (not dyed) and they were a huge pain to break in, but I don’t think they sell that color anymore and none of the recent reviews mention them being tough to break in so I think they’ve updated that! You can also buy direct from their website. Make sure to read sizing reviews as I think it’ll vary based on how your feet run.

New Balance Sneakers | Kizik Athens Sneakers

New Balance Sneakers (Sold at Nordstrom, Shopbop, Zappos, and Dick’s Sporting Goods!)

I’m pretty happy that the New Balance trend is back. (Remember when everyone had these in high school!?)

These sneakers make super comfortable walking shoes since they’re lightweight and have a good amount of support! I love the neutral colors (some may say that’s my favorite color) and wear them year-round with everything from jeans to athleisure. I wore these straight out of the box first thing, no break-in necessary, no rubbing–like walking on clouds! These run TTS.

Kizik Athens Sneakers | Best walking shoes for traveling

Kizik Athens Sneakers (Sold at Nordstrom and Amazon!)

(not sure if my code is still live, but if it is, it’s JESSKEYS for 15% off!)

I love a lot of things about Kizik sneakers. I’m sure you’ve seen them online—they’re the sneakers with a spring-back heel that lets you slide your foot right inside, no bending over or unlacing necessary. (Where were these when I was pregnant!?) The style is modern and simple, and honestly just works with a lot of casual or new styles when you want a sneaker look–they look really cute with any athletic/athleisure option and are so cushy to wear all day! (No break in!) These run big, go down 1/2 size!

Birkenstocks sandals

Birkenstocks: (Sold at Nordstrom, Zappos, and DSW!)

When I polled you all on your favorite walking sandals to log tons of miles in–so many of you replied BIRKENSTOCKS (!) due to their good arch support.

I can also attest that last time I was in NYC (walking capital of the world IMO) I saw girls in Birkenstocks EVERYWHERE. Though they’re sandals, they’re surprisingly supportive, because the cork footbed sort of molds to your feet for ideal support. This makes them comfortable sandals to wear all day!

The break-in period will really vary from person to person, but I recommend wearing them around inside (wearing with socks helps too!) so your feet get used to them, crafting the perfect fit, and then gradually wearing them for longer periods outside! I particularly LOVE the big gold buckle version because they feel a bit more elevated, but I also own the classic Arizona’s in gold, and the waterproof version, too! I ordered my regular size.

Madewell Charley Slides

Madewell Charley Slides (Sold on Zappos and Amazon too!)

If you want a slip on sandal that is supportive like a Birkenstock, but a little bit more minimalistic–you will love this sandal! It’s neutral, goes with everything and is very comfortable! The lug sole makes them a fun trendy option, too! So glad I’ve added these to my shoe collection!

Gucci Loafers (Left) (Sold at Nordstrom and Saks 5th Avenue!)

Absolutely an investment and I’m not huge on most designer things, but these are one of my favorite pairs of shoes that I own! They’re high quality and also a very classic shape so they will always be in style–a wardrobe staple for a long time to come. The leather is SO so soft, they feel like butter, and I always feel put-together when I put them on! I own them in black. I’ve worn them all over the country and to different countries on countless trips that include lots of walking.

Sizing: I went 1/2 size down in mine

Sam Edelman Lorraine Loafers (Right)

A very similar look (could even call them a dupe) to the Gucci loafer but a whole lot less! (Plus, they come in a lot more colors!) I love these loafers and have been a fan for many years–I own them in the caramel color. They’re super comfortable and I even wore them right out of the box with no blisters–zero rubbing at all! Truly, you can’t go wrong with either pair.

Sizing: True to size, take your normal size.

Sorel Emelie boots:

Another FAVORITE they brought back this year 🙌🏼 If you want a super weatherproof boot that isn’t bulky and super comfortable to walk in–these are them! A great pair of shoes for winter travel where you’ll be dealing with freezing temps, snow, and slush.

Blondo boots: (Also available at Tuckernuck and Zappos)

I have owned many pairs of Blondo boots over the years, and in addition to the Hallie I linked above, their tall boots are also always a go-to, especially in deep winter. There is a lot to love about Blondo–every style they make is waterproof (even the suede!) they’re stylish, and comfortable. They come out with a slightly different tall style each year, but this is the latest version! I like to style them with skinny jeans (see? There’s still a use for your favorite skinnies!) and skirts and dresses! Also worth noting, they’re one of the few tall boots that don’t fall down on my small calves!

Sizing: Take your normal size, at least in my experience! I would not recommend these to those with wide calves–but the stretchy back accommodates small to medium sized calves great (based on my own experience and what I’ve gathered from readers!)

Comfortable boots: more picks & reader favorites: 

Whether you have a cold weather trip booked or are in search of a new pair of comfortable boots for for the winter season, look no further than this reader-approved list of boots at a range of price points!

Blundstone Boots:  A super popular reader favorite with rave reviews in the boot category! One reader said they were the only pair of shoes she took to Ireland and they were the only pair she needed! Even did great on a hike. If you’re looking for casual, comfy, and ready for weather–look no further!

Sizing: normal size unless you have wide feet, then consider going up a size!

P.S. these Sorel boots are also a similar look, but the chunky thick sole makes them a bit trendier!

Blundstone Lace-Up Boots: Same boots readers love, but I love the patent leather and lace-up detail on these that make them easier to dress up for nighttime!

Thursday Boot Co. –   A brand I haven’t heard of before, but readers really love! They have an amazing selection of boot styles and colors at a great price point!

Nisolo Classic Chelsea Boots: another super popular reader suggestion. Designed for comfort and sustainably made, these boots are perfect for work and play. Also they’re on major sale right now!

Freda Salvador Brooke BootAnother popular suggestion–one reader said “steep, but the cost per wear=pennies!” These come in several colors, are water resistant and currently on sale!

Rothys Water-Resistant Lug Boots: Another Rothy’s fan favorite! Water-resistant, comfy, AND washable!

Bared Footwear Flat Boots–  I had to include a few styles from this brand because I own a pair of sandals from them and they’re amazing. They’re an Australian brand invented by a podiatrist. By far the most fashionable supportive shoes I’ve ever come across! Each pair has hidden arch support and can also accommodate your own orthotics. This style is so classic and the elastic panels sound like a dream for slipping on and off in the winter. The reviews are also amazing!

Bared Footwear Leather Heeled Boots- Heeled boots that are extremely comfortable? Yes. yes. yes. These get rave reviews, come in three colors and somehow hit both classic and modern style boxes!

Bared Footwear Leather Heeled Boots- Bared Footwear Meadowlark Flat Boots- Love this dark oak color! These look so luxe, yet still have the elastic sides and are orthotic-friendly!

Comfortable sneakers and slip-ons: more picks & reader favorites: 

Finding the perfect sneaker that is both comfortable and effortlessly “cool” can take a little trial and error, but you can’t go wrong with this roundup of reader-approved sneakers and slip-ons.

Rothy’s Slip on Sneakers: Comfy, easy on/off, and machine washable! A reader fave, but I also approve! Read my full rothys review.

Allbirds Wool Runners: I have owned and loved two pairs of Allbirds for years. So comfy (they feel like wearing socks!) and also machine washable.

Adidas Superstar Shoes: These are a streetwear staple and are becoming so popular! They have the smooth and softest leather upper with sporty 3-stripes and a heel tab, making them comfortable sneakers! Love that they also have 15 other color variations to match your personal style and preferences!

Birkenstock Clogs: They’re baaccckk and you all love wearing them everywhere from at home to on the go.
Ugg Olive High Top Sneaker: Multiple people suggested these for supportive, comfy, and warm high-top sneakers!
Classic Chuck Taylor High Top Converse: You can never go wrong with a classic. I love wearing these in the winter because they keep your ankles warm!

Comfortable sandals: more picks and reader favorites for warm weather

There is nothing worse than an ill-fitting sandal! The next time you’re due for a new pair of sandals, check out this list of reader-approved sandals — from rugged Tevas to more elevated styles and everything in between.

Alohas Harper Black Leather Sandal: I have seen ads for these on Instagram and you all seem to love them! Definitely a trendy, chunky look with thick soles, but very cute and they make a statement–they’ll make even a black tee and shorts look chic!

Alohas Beige Suede Espadrilles: A few of you mentioned wearing these all over Europe which is about the best testimonial I can think of. I love the espadrille touch to the classic sandal style and that they have ankle straps. So pretty.

Cole Haan Flynn Flat Sandal: Many submissions for the Flynn sandal! I love that it’s minimalistic and not too chunky of a sole if you don’t love that chunky look! A classic looking sandal that will always be in style.

Cole Haan Freya Sandal: If you need a bit more support than the Flynn, check out the Freya, which a few of you really love!

Cole Haan Mirabelle Sandal: Another cute but supportive option from Cole Haan!

Nisolo Flatform Sandals: Also a popular submission–you all love your Nisolo flatform sandals! They come in multiple colors and you love how cushy they are and how they go with everything from shorts to jeans to dresses.

Ancient Greek Sandals: One of the most recommended brands–they are the PRETTIEST sandals and they have a “comfort” line with tons of styles that have extra support with the cushion! I want to order a pair I just can’t decide because there are so many great styles!

Shop this collage of favorites: 1 / 2 / 3 / 4

Tevas: As you likely know by now, I LOVE my Tevas, and so do you all! From an outdoorsy weekend to a European vacation, many of you love your Tevas sandals for all sorts of trips.

Shop this collage favorites: 1 / 2 / 3 / 4

Birkenstock Glenda by Papillio: I had no idea Birks made sandals that looked like this! How cute! I love the platform–they look comfy enough to wear for a day of exploring but cute enough to pair with the most feminine dress! Very much considering investing in this pair!

Sorel Cameron Sandals: A cute option if you want a bit of a wedge! Many of you recommended various pairs of Sorel sandals. Zappos has a great selection and fast free shipping!

Chaco Townes: Alright, last but not least, if you need the MOST support, many of you feel VERY passionate about Chaco sandals. Their Townes style (also comes in a higher, trendy platform) is the most minimalistic leather style and ensures no matter how much support you need, you can stay on your feet all day with no issues! I will admit I was not a fan of these when I saw the product page, but when you see them styled on the model they actually look cute!?!

Bared Footwear Sandals: I am SO intrigued by this brand–invented by a podiatrist and every pair they make has HIDDEN support–so they don’t look like supportive chunky sandals at all, they’re sleek and minimal and so chic–they have tons of styles (not just sandals) so worth checking out their whole website if you’re looking for more support out of your shoes!

This list is comprised of mostly sandals as last time I polled you all was in summer, but I’ll continue to add to this list and poll you all again when the weather gets chillier!

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