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Hey Fashion Friend, What’s the Perfect Travel Shoe?

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Summer-travel season is on the horizon, and while I am personally a fan of the “frantically packing the night before” model of preparation, I agree that footwear is the one thing in particular that can really benefit from a little advance planning. The wrong shoes — and I’m not being hyperbolic here — can ruin a trip, or at least a precious portion of it while you move through the seven stages of wrong-shoe grief until finally accepting that you need to go out and buy an alternate pair. To circumvent this preventable fate, consider the suggestions, below.

If you have no room in your suitcase …

 H/t to Becky Malinsky’s newsletter for turning me on to this perfect blue-and-orange Waffle colorway. Photo: Harling Ross Anton

Your only footwear will be the pair your feet are already wearing. In this instance, you’ll want to go with what I would argue is the most useful travel shoe: a well-proportioned, non-athletic sneaker. Well proportioned is critical, because not every non-athletic sneaker looks right with non-athletic attire. I’m a fan of Nike’s Waffle and Daybreak models. They have a graphic, vintage look that screams “leisurely walk to go get ice cream” instead of “cardio,” which is the goal here.

Color is an important contributing factor as well. I feel strongly that neutrals like black and cream should be eschewed in favor of something that really pops, so that the sneaker looks more ornamental than practical. This is important because it’s inherently practical — you can walk for miles in these without a shred of discomfort. Intentional, eye-catching color serves to visually offset their practicality to some degree and ensures the shoes look like a thoughtful part of your outfit instead of a utilitarian afterthought.

The right socks are critical, too. Please do not, I beg of you, wear those little “no-show” socks with this type of sneaker while traveling. Proportionally, it just doesn’t look right. You’re going to want something that lands above the ankle, ideally on the thicker side with a ribbed cuff. My go-tos are these white crew socks from Hue.

If you have room in your suitcase for one pair …

My beloved brown leather Ancient Greek Sandals. Here is the same style secondhand in a size 7, for $48. Photo: Harling Ross Anton

If you’re already wearing the well-proportioned non-athletic sneakers in transit, and you have room for one more additional pair in your suitcase, I would opt for a comfortable sandal. Birkenstocks are a summer travel staple for me and always will be, regardless of whether they happen to be in or out of style. I have the classic white ones, but I’m eyeing the all-red ones to round out my small collection. They require a bit of breaking in, but once you’ve worn them a few times, you can wear them for miles and miles of walking. For a sandal, the arch support is unparalleled.

If you’re not a Birkenstocks person, or you need to prioritize a more streamlined style for certain occasions over the course of your travels, I recommend Ancient Greek Sandals. It’s my favorite brand for simple, comfortable, chic sandals, made from buttery soft leather that doesn’t need any breaking in. Most of the styles don’t offer any arch support, so maybe not the best choice if you’re going on some kind of trek, but otherwise, I’ve easily traversed a whole city in these with no problem.

If you have room in your suitcase for two pairs …

Photo: Harling Ross Anton

You’re wearing the sneakers, you’ve already packed the sandals, and you’ve got room for one more pair of shoes — lucky you! In that case, I would add your most comfortable pair of loafers. My go-to travel loafers are a simple brown leather croco-style pair from Mansur Gavriel that I got in, like, 2017. They don’t make them anymore, sadly, but I found a similar pair here.

Another option is the suede Sacca Donna loafer from M.Gemi. Maybe the softest shoe I’ve ever put on my feet, but somehow still structured enough that they don’t feel unsupported or flimsy. They were comfortable from the first wear and didn’t need any breaking in, which is pretty much unheard of for a loafer. An ideal travel shoe.

No matter how comfortable the loafers you pack are, though, I do recommend bringing a couple pairs of socks to go with them just in case. For loafers, I like a slightly thinner sock. These from Uniqlo are great and come in a ton of colors.

Final bit of advice …

If you end up winging it where travel footwear is concerned, at least toss one of these blister sticks into your toiletry bag. They actually work, especially if you apply before the blisters start to form, and might spare you from wrong-shoe agony for a little while longer.

Hey Fashion Friend, What’s the Perfect Travel Shoe?