The number one piece of advice I give before every trip is: Wear. Comfortable. Shoes. I say it again and again and again. And still, someone usually shows up wearing something cute but stiff — the kind of shoe that looked great in the store and is going to ruin day two in the souks. Especially at our age, comfortable shoes are the number one entry on a packing list. And maybe number two and three as well.

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There is always a good bit of walking on our trips — sometimes on the cobblestones of an ancient city, sometimes on the soft sand of a wine estate, sometimes through a crowded market where the ground is anybody’s guess. The shoes can make or break your experience. We’ve seen women limp through otherwise magical afternoons, counting the minutes until they can get back to the hotel. Don’t be that woman.

The good news? You don’t have to choose between comfort and looking like yourself. The options below are shoes you can wear with jeans or a sundress, on a walking tour or to dinner. We’ve organized them by type so you can find exactly what suits your style and your trip.

To see a catalog of these styles all together, click here.

Sneakers

1. On Cloud 6

If you’ve noticed a lot of stylish women wearing shoes that look like they’re walking on bubble wrap, those are probably On Clouds. The Swiss-engineered Cloud 6 has become something of a travel talisman — slip them on via their ingenious speed-lace system and you’re ready for cobblestones, museum marble, and everything in between. It’s the brand’s most popular shoe of all time, and it appeals to all ages — stylish enough for a city exploration, comfortable enough to wear all day, every day. Comes in a dizzying array of colors, from classic white to dusty rose. Pair with cropped jeans or a midi skirt and no one will ever accuse you of being sensible.

2. Sorel Kinetic Ember Sneaker

My fondness for SOREL shoes should be well known, since I talk about them all the time, have about seven pairs and never go on a trip without at least one SOREL in my suitcase. SOREL is best known for its indestructible winter boots, but the Kinetic Ember shows the brand has range. Inspired by ’70s runners, this sneaker blends suede and leather overlays in a streamlined shape — lightweight textile upper with an EVA footbed and SOREL’s Evertread™ rubber outsole for both cushion and traction.

We’ve seen women limp through otherwise magical afternoons, counting the minutes until they can get back to the hotel. Don’t be that woman.

The fawn/black colorway in particular has a warm, earthy sophistication that doesn’t read as athletic — it works just as well with straight-leg jeans or linen trousers as it does with leggings. If you’re the kind of traveler who wants a shoe that looks like it has a point of view but feels like a running shoe, the Ember earns a spot in the bag.

3. Sam Edelman Poppy Lace-Up Sneaker

The Poppy has a cult following, and once you try it, you’ll understand why — and probably end up owning several pairs in different colors like so many devotees do. It comes in an assortment of colors, but I prefer silver since it basically will go with everything and will jazz up any outfit. It’s a polished platform sneaker with buttery-soft leather that requires zero break-in time, a 1-inch platform that gives you a little lift without any instability, and a clean, classic silhouette that works just as naturally with a sundress as with jeans. The soft silver leather colorway in particular is the kind of versatile neutral that goes with everything and looks far more expensive than $100. Reviewers have worn them across cobblestones in Paris, through airports, and on full travel days — and come home asking where to buy the next pair.

4. Danner Rivercomber

Danner has been making serious footwear since 1932, and the Rivercomber is their answer to the question nobody thought to ask: what if a water shoe were actually built well? The Cordura knit upper is breathable and abrasion-resistant, the midsole is drainable and ultra-lightweight, and the Vibram Rivercomber outsole uses Wavegrip technology to direct water away from the foot for grip on wet surfaces — all atop a removable OrthoLite footbed for cushioning and support. The sand/bluebird colorway is unexpectedly chic — earthy and cool at once. This is the shoe for trips that might take you somewhere wet: a boat excursion, a river walk, a morning on a rocky coast. It slips on and off easily, dries fast, and won’t leave you hobbling when the adventure gets a little unpredictable.

Flats and Ballet-Style Shoes

5. Allbirds Tree Breezer

Not every flat has to announce itself. The Tree Breezer’s stretchy fitted collar provides exceptional flexibility made to move with you — lightweight, breathable, and effortlessly sleek from first step to last stop. If you want a little more polish, the Mary Jane version adds a delicate strap that makes the shoe look intentional with a skirt or wide-leg pants. Made from eucalyptus fiber, they’re also machine-washable — which, after a long day in a market, is not nothing. Versatile enough to dress up or down for any outing or outfit, with a sugarcane-based outsole for cushy all-day support.

6. Dansko Milana

Fashion editors have started calling this category the “sneakerina,” and the Milana is the original. It works double-time as a fashion sneaker and a polished ballet slipper all in one, with a removable footbed featuring memory foam and Dansko Natural Arch technology for all-day support. The suede upper has a quiet luxury feel — especially in the chocolate-and-pewter or black-and-vanilla colorways — and it moves easily from a museum to an outdoor café without skipping a beat.

7. Vionic Alameda Mary Jane

For women with any degree of foot sensitivity — plantar fasciitis, wide feet, the general wear of a life well-walked — Vionic is a gift. The Alameda’s built-in VIO MOTION Technology footbed features contoured arch support, shock-absorbing cushioning, a deep heel cup for stability, and forefoot flexibility. The Mary Jane strap adds a sophisticated touch that works with everything from tailored trousers to a floral dress. APMA-approved, which means even your podiatrist will give it a thumbs up. And leopard print is NextTribe’s signature print (though they come in other colors too).

8. Naturalizer Mary Jane Sneakers

Naturalizer has come up with a pretty ingenious hybrid–the style of a Mary Jane plus the comfort of a sneaker. I absolutely love the versatility. Naturalizer has been in the quiet comfort business for decades and continues to earn its place on every smart packer’s short list. The brand’s Contour+ cushioning system adds softness at the heel and forefoot with moderate arch support — genuinely wearable for a full day on your feet. The styles have gotten considerably more interesting in recent years, with pointed toes, metallic leathers, and clean silhouettes that hold their own with anything in your travel wardrobe.

Loafers

9. Vionic Uptown Loafer

Here is a loafer with a secret superpower: it collapses flat for packing. The Uptown is smartly deconstructed with a buttery-soft unlined upper and a featherweight, flexible sole — so it tucks into a corner of your suitcase without complaint, then springs back into shape ready for a full day on your feet.

Here is a loafer with a secret superpower: it collapses flat for packing.

Backed by Heeluxe performance testing, it delivers the same VIO MOTION Technology footbed found across the Vionic line: contoured arch support, shock-absorbing cushioning, and a deep heel cup for stability. APMA-approved and available in a staggering range of colors and materials — from sleek black leather to gold metallic to dark denim suede — the Uptown is the rare loafer that works equally well with tailored trousers, jeans, or a midi skirt. Over 3,700 reviews, and the recurring theme is the same: women buying their second, third, and fourth pair.

10. ECCO Suede Loafer

ECCO is the brand that quietly converts everyone who tries it. Designs that feel timeless while still being fashion-forward, made using a special process that fuses the sole and top together for exceptional durability — the kind of shoes you wear for years without worrying about them falling apart. Their loafer and slip-on styles are particularly good for travel: structured enough to look polished, with leather uppers that soften and mold to your foot over time. A solid neutral pair of ECCO loafers might be the most cost-per-wear-efficient shoe you ever buy.

Sandals

11. Birkenstock Siena Chunky

Yes, Birkenstocks. If you haven’t revisited them since the ’90s, it’s time. Especially for the Siena, which with its criss-cross straps doesn’t look like your averge Birks. The footbed — that famously contoured cork-and-latex base — is genuinely orthopedic, and it molds to the shape of your foot over time. Some travelers walk ten miles a day in Birkenstocks with absolutely no pain. Both have become fashion staples. Style with linen trousers or a flowing skirt and you’ll look like you know something other people don’t.

12. Teva Universal Sandal

Teva has long since outgrown its camp-counselor reputation. The Universal sandal holds up in all sorts of warm weather — feet don’t slide out in a rainstorm — with cushioned comfort and woven straps that work for a range of activities, from cobblestones to waterfall hikes. At this price point, they’re also guilt-free if you wear them every single day for three weeks straight, which you probably will. The newer styles come in sophisticated neutrals and patterns that work with almost everything warm-weather.

13. Sorel Kinetic Sunchase Ankle Strap Sandal

Here I am again with another SOREL. I like that their sandals are built on a sneaker sole. SOREL built its reputation on serious winter boots, but their Kinetic collection proves they know summer just as well. The Sunchase Ankle Strap is the sandal for women who want something more polished than a sport sandal but more substantial than a flip-flop.

I like the red and actually own a pair of SOREL red sandals that I take great pride in wearing.

The lightweight molded TPU upper features adjustable straps for a comfortable and secure fit, with an EVA footbed and midsole that cushion every step. It comes in a range of sophisticated colors — but I like the red and actually own a pair of Sorel red sandals that I take great pride in wearing. They pair as naturally with linen trousers as with a sundress. At $100 (and frequently on sale), it’s excellent value for a sandal that will carry you from morning market to sunset dinner without complaint. Size note: this style runs only in full sizes, so if you’re between sizes, go down.

14. Vionic Tide 2.0 Thong Sandal

A thong sandal with actual arch support — it sounds too good to be true, but Vionic pulls it off. The Tide 2.0 is built on the same biomechanically designed footbed as the rest of the Vionic line, which means your foot is supported in all the right places even when wearing the simplest possible silhouette. Available in leather, nubuck, and metallic finishes, it pairs as well with a maxi dress as it does with shorts. Keep a pair in the bag for dinners when the sneakers feel like too much.

15. ECCO Flowt Wedge Cork Sandal

When you want a little lift without the liability of a heel, a low wedge is your best friend. This wedge sandal features a footbed that molds to the foot, a lightweight platform, and a Velcro ankle strap — designed for all-day comfort in warm climates and polished enough to wear with travel dresses. The cork platform gives it an easy, resort-y feel that travels from afternoon sightseeing to dinner without changing.

The Budget Buy

16. Rykä Jumpstart Slip-On

If you want the comfort and function without the investment price, Rykä deserves a look. The brand makes its footwear specifically with women’s feet in mind, and the Jumpstart slip-on offers soft cushioning and stylish colorways at some of the most affordable prices in this category. The slip-on design is airport-friendly, the cushioning is genuine, and the price makes it easy to grab a pair specifically for a trip without agonizing over it.

One final note: Whatever you choose, break them in before you go. Wear them around the house, to the grocery store, on a long errand day. Even the most comfortable shoe deserves a trial run before you ask it to carry you through eight hours in Florence. Your feet — and your travel companions — will thank you.