The Most Comfortable (and Cute!) Walking Shoes for Travel

If you’ve been around for a while, you know that walking a lot is one of my favorite things to do just about anywhere in the world.

Living in New York means that my standards for travel shoes – stylish, but comfortable for walking – now apply to my whole closet. (Except for a couple pairs that are strictly taxi-only, but that’s not why we’re here.)

this post contains affiliate links and codes, which contribute to my oat-milk cappuccino fund at no extra cost to you. thank you!

If you don’t want to scroll through this list, I’ll send you straight to the source. My two favorite cute-and-comfy shoe brands are Sarah Flint (save $50 with this link) and M. Gemi (save $50 with this link). They’re both small, independent companies whose shoes are made in Italy and designed to be triple threats of style, comfort, and quality.

My Favorite Cute & Comfy Shoes for Travel

1. White Leather Sneakers

One pair of white leather sneakers lasts me about two years – I wish they had a mile counter, because my last pair has logged a zillion across in NYC, Japan, Savannah, Greece, New Orleans, and more.

They’re my go-to for long, casual walking days wherever I am. This French style also comes in black suede, and try these if you’d rather have canvas.

→ Use this link for $50 off the white leather sneakers.

2. Ankle Boots

During the colder half of the year, neutral ankle boots see me through all kinds of outfits, destinations, and weather.

This zip-up pair is replacing my v. dead black boots from 2014, and I just bought this pair in white a few months ago. If all the high heels and zips seem fussy to you, try this slip-on pair.

→ Use these links for $50 off the zip-up pair, $50 off the slip-ons.

3. Lowland Boots

The winter I got these boots was my feet’s happiest yet. They definitely fall into the “investment” category, and I’m so glad I sprung for them on sale. They fit like a glove, keep my legs warm, look fantastic, and have never caused me pain.

There are plenty of imitations of these boots out there, but it’s hard to imagine they’re anywhere near this great. And look, the real ones are on sale right here!

Quick tip: fold the boots in half when putting them on or taking them off. Instead of basically trying to put on thick suede tights, you’re now just pulling on a calf-height boot and unfolding the rest.

4. Actually Comfortable Flats

Oh, ballet flats. They’re so classic, and fashion magazines talk about them like they’re made of marshmallow fluff – but my feet know better. To really walk in them, they must be comfy to the core, and that’s surprisingly hard to find.

A question: do you like bows? If yes, get these; if no, get these.

→ Use these links for $50 off sans bows, $50 off avec.

5. Brogues

Aka oxfords, derbies… I count my monk strap flats in this category, too! I had kind of written off this style of shoe until I popped into Sézane a few years ago, bought this pair, and proceeded to traipse around the whole freaking world in them.

While the monk strap flats are good to go with just a hidden sock, there’s room in the Sézane pair for an extra cushion if you like – though I skip it and have zero complaints (and years left of wear in the shoes!).

P.S. These are my dream brogues. 😍 It’s important to have goals.

→ Use this link for $50 off my monk strap flats!

6. Espadrille Flats

Okay, I’m not suggesting that you wear these to walk the length of Manhattan – but they’re still part of my regular cute-walking-shoe rotation in spring and summer. Keep them for days with less walking, but still enough that potentially uncomfortable shoes need not apply.

I’m on my second pair of these striped espadrilles in four years, and they’re a standard part of my comfy shoe rotation whether I’m in New York or Rome. The newest addition to my espadrille arsenal is this cap-toe slip-on version that I brought on safari!

7. Loafers

If I were handing out shoe awards, this one would win Most Polished Look & Lazy Feel. I swear these suede loafers are like walking on butter – in a very non-greasy way.

Those do have a short block heel, so if you want a flat try these. If you prefer leather, go for this gorgeous pair. Also of note: the loafer-adjacent moccasin is alllllllmost actually a slipper.

→ Use these links for $50 off the suede loafer flats & moccasins, $50 off the suede butter loafers & leather flat ones.

8. Mules

50% loafer, 50% sandal. Like the espadrilles, these aren’t suited for a huge trek, but they’re great for some city or museum exploring. I’ve strolled the world over in a pair of black leather mules, and here’s a suede version for good measure.

→ Use these links for $50 off the suede ones, $50 off the leather ones.

9. Sandals

For summer, when you’re walking through gardens, up the Positano steps, or out to the beach. If you’re ever in Greece or Italy or the French Riviera, buy yourself some locally made sandals. They’re theeeee best!

For a passport-free option, I love these sandals inspired by Roman Holiday, these easy slides made in Italy, or this brand of greek sandals available stateside.

→ Use these links for $50 off the slides, $50 off the Roman Holiday ones.

Shop the Best Cute & Comfy Walking Shoes for Travel

Pin This Post for Later