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product images for DSW | TOMS Shoes | Aerosoles
DSW | TOMS Shoes | Aerosoles

12 Pairs of Comfortable Heels for Travelers

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Whether you need heels for standing all day or a pair of comfortable heels to travel with, this list of shoes has you covered.

Comfortable Heels for Travelers to Pack

Each pair of comfortable heels was evaluated for their versatility, comfort, customer reviews, and packability.

Anne Klein Xiana Bootie

high heel sport booties

  • Versatility: 4. The sporty-casual heel can easily be dressed up or down, and the solid black color goes with most outfits. The rubber sole provides good traction in all sorts of weather.
  • Comfort: 4. Reviewers rank this pair of heels high on the comfort scale.
  • Packability: 3.5. With a longer heel, these shoes will take up space in your suitcase, but it’s pretty easy to pack around them.
  • Reviews: 31 five-star reviews. Standout review: “These booties are extremely comfortable. The padding is perfect for reducing pressure on my feet and the heel is perfect for standing longer than expected.”

 Pashion Footwear

black patent leather interchangeable heels
Pashion Footwear

  • Versatility: 5. A comfortable heel that also converts to a flat? Sign me up. These convertible heels can be worn in two different ways: as a flat or as a four-inch high heel.
  • Comfort: 4. With the quick ability to transform these shoes into flats, you’ll get instant comfort without a heel.
  • Packability: 5. These comfortable high heels are really two shoes in one. They even come with their own handy carrying case.
  • Reviews: There are 16 five-star reviews on the Pashion website. Standout review: “These women are genius! Love, love, love my new shoes, the three-inch heel that I got also is perfect for me on my feet all day–now make it in every color!”

TOMS Emmy Boots

leopard print and black boot
TOMS Shoes

  • Versatility: 4.5. Whether you pick a trendy animal print or neutral color, these boots go with almost any outfit or occasion.
  • Comfort: 4.5. The block heel makes standing in these heels all day a breeze, and you can even hustle through an airport in them comfortably (trust me).
  • Packability: 3.5. While these are a boot and thus take up a little more space in your suitcase, this pair of comfortable heels might be the only pair of shoes you need on a weekend trip.
  • Reviews: No reviews are available on the website, but I personally tested these in the leopard print and haven’t taken them off. Plus, I’ve gotten tons of compliments and even convinced a few other people to buy them after wandering around in them over a long weekend in New York City.

TOMS Leilani Booties

comfortable low ankle boot
TOMS Shoes

  • Versatility: 4. These comfortable heels are a classic take on the ankle boot and can be worn in all seasons.
  • Comfort: 4. With an OrthoLite Eco X40 insole and sturdy block heel, our tester rated these heels high in comfort.
  • Packability: 4. As an ankle bootie, these don’t take up too much space in your suitcase and could be a contender for a “one shoe” trip.
  • Reviews: No reviews on the website, but our tester loved these shoes right out of the box, getting major style points.

Aerosoles Deal Breaker

aerosoles leather heel

  • Versatility: 3.5. For travelers needing a business heel or proper stiletto, these comfortable heels are for you.
  • Comfort: 3.5. Aerosoles goes above and beyond to make these pumps comfortable. From a memory foam insole to a patent-pending heel rest design, these really are the most comfortable pair of proper heels you’ll find.
  • Packability: 3. Unfortunately, there’s not much you can do about packing an awkwardly shaped pair of shoes, but if you need a pair of comfortable high heels, these are your winners.
  • Reviews: Highly rated on Aerosoles site at 4.5 stars. Standout review: “Bought these pumps and my feet are in heaven! Don’t even think to kick them off when I come home. Great purchase!”

 Aerosoles Eye Candy

low suede and leather comfortable heel

  • Versatility: 4. This low, block-heel shoe is casual enough for light walking or dressy enough to wear to a formal event.
  • Comfort: 4.5. Like many Aerosoles shoes, this pair of comfortable heels is made with comfort technology and even a removable footbed.
  • Packability: 4. When tested, these shoes didn’t take up as much room as you would think, making them the perfect pair of heels to throw in your weekend bag “just in case.”
  • Reviews: Highly rated on the Aerosoles site at four stars. Standout review: “Having the block heel is so comfortable, even with my problem knees. Didn’t have to change into flats later in the day!”

Cougar Devlin Boot

wedge snowboot

  • Versatility: 3.5. A wedge-heel snow boot? Why, yes, this is actually a thing and they’re incredible. For fall and winter travels these heeled boots look stylish and hold up to rain, snow, and colder temps.
  • Comfort: 4. I personally tested these and my feet felt comfy and warm all day.
  • Packability: 3. These heeled boots are going to take up a decent amount of space, but since they’re so versatile, you could wear them on the plane and not look like you’re headed out to shovel your driveway.
  • Reviews: 4.65 stars based on 75 reviews on Cougar’s website. I personally tested these and after wearing them felt like they were the fall/winter boot I didn’t know I needed.

Everlane Day Heel

comfortable heels everlane

  • Versatility: 4.5. There are tons of color and material options for these heels, so it’s hard to pick just one. No matter your choice, these comfortable heels for travelers look just as good waiting in the TSA line as they do at happy hour.
  • Comfort: 4.5. I’ll let the reviews speak for themselves (there are over 4,000 of them). People love these for their comfort features: low heel height, soft leather, and elastic back.
  • Packability: 4.  This pair of comfortable heels is slightly scrunchable, so they take up a little less space than normal heels would in your bag.
  • Reviews: There are over 4,200 reviews on these comfortable heels, with an average rating of 4.39 stars. Standout review: “I loved these shoes right out of the box. I can’t/don’t normally wear heels because they aren’t easy for me to walk in and aren’t comfortable. These are different—easy to wear/walk with the wide block heel, I don’t feel wobbly. Soft, buttery leather and cushy insole are great on my feet. These are perfect for work or a night out and really cute with cuffed jeans!”

 Naturalizer Vera

comfortable heel red block

  • Versatility: 4. If you’re in need of a pair of traveling shoes for parties, this pair of heeled sandals is especially great for outdoor weddings and events.
  • Comfort: 4. The low block here is comfortable and supportive, plus the insole is cushioned and the outside is flexible and non-slip for extra stability.
  • Packability: 3. Since these are heeled sandals, it’s pretty easy to pack around this pair of comfortable heels.
  • Reviews: These shoes have over 25 five-star reviews on the Naturalizer site. Standout review: “I love these shoes! With this style, it is hard to find a comfortable shoe. These are very comfortable. The leather is soft and the heel isn’t too high, but is high enough to look nice.” 

Cole Haan Grand Ambition Pump

comfortable heel snakeskin print
Cole Haan

  • Versatility: 3.5. Currently, these are one of Cole Haan’s best-selling pairs of shoes, and while the snakeskin is a specific taste, it’s actually surprisingly versatile. The pump style is specific for those needing to dress up a bit more, but why not wear them all the time if they’re this comfy?
  • Comfort: 4. These are the most comfortable pair of heels, according to science … yes, you read that right. Cole Haan worked with the University of Massachusetts Amherst’s Biomechanics Laboratory to create a shoe collection, called Grand Ambition, that maximizes fit, feel, flexibility, and cushioning.
  • Packability: 3.5. The pump style is slightly awkward to pack.
  • Reviews: Right now there are seven five-star reviews on Cole Haan’s site. Standout review: “Cole Haan has found the secret to combining comfort with style! This will be the most gorgeous, comfortable shoe you own! Bought them in every color and pattern available so far.”

Cole Haan Emory Bow Wedge

cole haan tan wedge heel
Cole Haan

  • Versatility: 4.5. The bow adds a feminine touch while the patent leather makes for a more polished look. You can easily wear these on the plane, out to dinner, or to an event.
  • Comfort: 4.5. With a fully padded sock lining and tons of “these shoes are so comfortable” reviews, these wedge heels won’t blister or make your feet sore.
  • Packability: 4. These shoes are slightly crushable, so you shouldn’t have too much of a problem fitting them in your suitcase.
  • Reviews: Rated 4.8 stars on Cole Haan’s website with 30 reviews. Standout review: “These are the most comfortable shoes I have ever had, even better than my sneakers. This is the 4th pair I own.”

Dream Paris Low-Chunk Low Heel Pump Sandals with Ankle Strap

tan block heel shoe

  • Versatility: 4. I have three different pairs of these shoes and have worn them at just about every summer event, from weddings to backyard cookouts. They can look casual or be dressed up for a special occasion and are available in dozens of colors and prints.
  • Comfort: 3.5. For the price, these really can’t be beaten. I can comfortably wear them for an evening out or a day event. Given the lower price, they don’t have any fancy comfort technology, but that doesn’t mean they aren’t comfy.
  • Packability: 4. It’s easy to pack other items around these comfortable heels since it’s an open sandal style.
  • Reviews: These shoes are rated as a 4.3 with over 400 reviews on Amazon. Standout review: “These shoes are great! They’re so flattering and well made. I was nervous about getting blisters but wore them for about 8 hours and only started getting pain towards the end. They were right on the pinky toe and under the clasp, but nothing a bandaid can’t fix. Overall I am SO HAPPY with this purchase and will definitely be buying another color!”

Padded Socks

padded socks flat lay

When you’re really in a pinch and need to make any pair of your current shoes comfortable, purchase a pair of padded socks. I almost always travel with these, especially with a new pair of shoes.

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Ashley Rossi is always ready for her next trip. Follow her on Twitter and Instagram for travel tips, destination ideas, and off the beaten path spots.

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We hand-pick everything we recommend and select items through testing and reviews. Some products are sent to us free of charge with no incentive to offer a favorable review. We offer our unbiased opinions and do not accept compensation to review products. All items are in stock and prices are accurate at the time of publication. If you buy something through our links, we may earn a commission.

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