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The 39 Best Shoes for Travel: Handpicked by an Expert

I was in the streets of Santa Fe when I made this vow: No more bad shoes. I didn’t raise a pair of problem pumps over my head, a la Scarlet O’Hara, when I declared that, but it felt just as dramatic to me. I had brought a pair of cute Western-inspired booties on our NextTribe Santa Fe trip two years ago, thinking they were just right for the city’s vibe. Yes, they were killer—in looks and in what they did to my feet and all the joints up and down my legs. Why in the world would I do this to myself? It was ruining my fun.

I’ve tried on hundreds of shoes between then and now, bought many of them, returned a good percentage.

Having made that promise to myself, I became obsessed with finding shoes that could take care of my poor feet, knees, and hips, but didn’t look like something prescribed by a 19th-Century podiatrist. I’ve tried on hundreds of shoes between then and now, bought many of them, returned a good percentage. The ones I’ve kept have fallen into two categories: the ones that have proved disappointments over time (you know, after I’ve worn them outside and couldn’t take them back) and the ones that have become my all stars. (See below.)

Best Shoes for Travel: The End of Bad Choices

I’ve taken scores of women on trips across the globe and I’ve learned that I’m far from alone in the Footwear Fail Department. I’ve tended to a woman who cried from blister pain after running through an airport in flat mules, and another one who was on a mission in Paris to replace the Gucci loafers that were too chic for her own good. It makes me crazy to see anyone sacrifice comfort for the sake of style when these days that’s completely unnecessary. On most of our NextTribe trips, we do a fair amount of walking—in Paris, through towns in Umbria, all over the cobblestone streets of San Miguel de Allende, Mexico. Who wants to be dragged down by footwear that digs or scrapes or pinches or makes your soles or calves ache? That’s why I’ve put together a list of the best shoes for travel.

I’ve learned how to buy good shoes the hard way.

This list was easier to put together than I imagined because so many brands–from Adidas to Cole Haan–have gotten smart and started offering shoes that look as good as they feel. Plus, new companies have sprung up that are entirely devoted to comfort. There are also websites that only sell comfort shoes, such as the Walking Company, my first stop when looking for shoes these days. And I was thrilled to come across a company called Kuru that helps you find shoes based on your specific problem area, from flat feet, to bunions, to back pain. You can bet I’m trying out the recommendations for knee pain.

Please notice that none of these picks are heels because really, why? You can wear most of these styles with skirts and dresses and look as good as you would in any pump. (Though I have included some with big juicy soles that give you the heigth a heel would.)

Of all the things you pack, shoes are the most problematic since they take up so much space. I try to pack no more than four pairs and I make sure I can walk all day in any one of them.

Here are my greatest hits, some of which you’ll see me in if you come along on a NextTribe trip. Look for my picks for sandals and warm weather shoes, coming in the spring.

By the way, we receive no commission off the sale of these shoes. We just want you to have the information so that you can enjoy yourself more when we see you.

Click on the red arrows in each category to see all the styles.

In My Own Suitcase

After much trial and error, I’ve ended up with these four go-to pairs. I keep to a four-pair limit on any trip I take, no matter how long it is. I wear the clunkiest pair through the airport, the other three are in my bag (almost always a carry on).

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Sneaker Brands Go Glam

I love seeing what New Balance, Adidas, Nike, and Saucony are doing to up their style game.

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I was never a fan of the ’80s big-hair band, but I sure do like the finish to add a bit of panache to a standard sneaker or slip on.

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Slipping Into Comfort

Shoes that you can just slide into without bothering with closing up are ideal for making it through TSA. (Why are we still taking shoes off by the way?) Salute to Martha Stewart and the hands-free version she hawks on TV.

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The Loafer Life

There’s a reason loafers have been a wardrobe staple for decades. But for me, loafers can feel a little inflexible, with hard leather soles and uppers that don’t give. That’s why I like the new twists on loafers here for women who are anything but loafers.

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Off to the Laces

Often nothing beats laces for getting the fit snug and offering maximum support. Here are some smart versions to get you tied up right.

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Getting the Boot

Now that fall is upon us, you may want to take a short boot along. These look great with tights and skirts when it’s chilly out.

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Extra Flair

If you’re like me, you like a bit of zing on your feet to elevate the style and make a statement (as in, “These are not my grandma’s orthodics.”)

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The Shoe Hack

If you don’t have the budget for more shoes or much packing space, one simple solution is to get a great pair of orthotic inserts and slide them into whatever shoe you have. I’ve used SuperFeet inserts numerous times while searching for my forever footwear.

By Jeannie Ralston


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