Shoes are the hardest part of packing. They're bulky, they're heavy, and everyone always brings too many. You pack five pairs, wear three, and wonder why your bag weighs what it does.
Here's a better approach: fewer pairs, chosen more carefully. Here's how to think about it.
The rule we pack by: three pairs maximum
For most vacations — a week at the beach, a long weekend in a European city, a resort stay — three pairs of shoes covers everything. The framework is simple:
One pair for walking. Your most comfortable shoe, the one you'd wear for a full day of cobblestones, markets, or exploring. It needs to look good and feel good for hours.
One pair for evenings. A heel, a mule, or a dressy sandal — something that elevates an outfit for dinner, a rooftop bar, a boat. Doesn't need to be comfortable for all-day wear, just for a few hours.
One pair for the water or beach. A flat sandal you can get wet, wear to the pool, or walk from the beach to a café without overthinking it.
That's it. Three pairs. Mix and match across your outfits and you'll have everything you need.
The exception is if you're genuinely mixing activity types — hiking and dinners, say — in which case a fourth pair makes sense. But most vacation wardrobes don't require it.
The walking shoe: why leather mules are better than you think
The instinct is to reach for sneakers for a walking-heavy vacation. Sneakers are comfortable, sure, but they're also casual in a way that limits your outfit options, and most of them don't pack particularly small.
A well-made leather mule on a platform or low heel is a better choice for most warm-weather destinations. Here's why:
They go with more. A leather mule in whiskey or black works with linen trousers, a midi dress, shorts, a swimsuit cover-up. A white sneaker works with casual outfits and little else.
They're easier to get on and off. Through airport security, on and off a boat, in and out of a restaurant. No laces, no faff.
They get better with wear. Full-grain nappa leather softens and molds to your foot over time. By day three of a trip, a leather mule that was slightly stiff on day one will feel completely broken in and perfectly fitted.
They're lighter than they look. A leather upper on a wood platform is lighter than a chunky sole sneaker.
The one caveat: break them in before you travel. Wear them around the house for a few sessions, then on a short errand. Don't debut a new pair of shoes on vacation day one. See our guide to breaking in leather shoes for the full process.
Fortress pick for walking: Ava Platform Clog — open back, easy to slip on, platform heel that's comfortable all day. Available in whiskey, black, and olive nappa. This is the shoe that goes on in the morning and comes off at dinner.
The evening shoe: a heel you'll actually wear
The evening shoe is the one most people overpack for. You bring three options, wear one, and haul the rest home untouched. Pack one good one and commit to it.
What makes a good vacation heel:
Low to mid height. A 2–3 inch heel is walkable. A 4-inch stiletto is not, especially on cobblestones or uneven resort paths. Save the statement heel for home.
Neutral or versatile color. Black, camel, nude — a heel in a neutral leather goes with everything you packed and doesn't require outfit planning around it.
A silhouette that works across contexts. A strappy sandal heel or a heeled mule covers dinner, a night out, a wedding, a boat party. A platform boot does not.
Fortress pick for evenings: Milla Mule Sandal — an open-toe heeled mule in nappa leather that hits the sweet spot between casual and dressy. Wear it with a linen set for a resort lunch, a silk slip dress for dinner. Available in bone, coal, and natural jute.
Or for more of a statement: Rachel Heeled Sandal — a strappy sandal heel in cobalt or coral suede that works as the centerpiece of an outfit rather than an afterthought.
The flat sandal: your workhorse
The flat sandal is the shoe that does everything. Beach to breakfast. Pool to market. Boat to bar. It needs to be comfortable, get-wet-friendly (or at least not ruined by a splash), and look good enough to wear into a café.
What to look for:
A sole with some grip. Slick leather on wet tile is a problem. A rubber outsole or rubber-capped platform is safer.
A secure fit. Flip-flops are fine for the pool but not for walking any real distance. Look for a strap or backstrap that holds your foot in place.
Something you don't have to think about. The flat sandal should be the easy choice, not the deliberate one.
Fortress pick for flats: Leja Flatform Sandal — a leather flatform sandal with a slight platform and a secure fit that bridges the gap between a flat sandal and a low heel. Comfortable enough for all day, polished enough for dinner if needed. Available in cedar, cactus, and gloss black nappa.
Or for a true flat: Golde Fisherman Sandal — a woven leather fisherman sandal in chocolate nappa. Casual, comfortable, completely versatile.
What to leave at home
Heels that require concentration. If you have to think about every step, leave them. Vacation is supposed to be relaxing.
Shoes you haven't broken in. This is the rule everyone breaks and regrets. Don't debut new shoes on a trip. Blisters on day two are a tax on the rest of the vacation.
More than one pair of sneakers. One, if you need them for an activity. Zero if you don't.
Anything you wouldn't be sad to leave behind. If it gets wet, sandy, or lost in transit, is that okay? If not, leave it.
Packing the shoes
A few practical notes:
Pack shoes in the corners of your bag, not in the middle. They're the densest item and help create structure around clothing.
Stuff socks or small items inside shoes to save space.
Use shoe bags or shower caps over the soles so they don't transfer dirt to clothing.
Wear your bulkiest pair through the airport to save bag space — typically boots or platforms if you're bringing them.
The Fortress vacation edit
All of our shoes are made by hand in Peru using LWG-certified leather. They're built to last, which means they'll travel with you for years, not just one trip.
Ava Platform Clog →
Milla Mule Sandal →
Leja Flatform Sandal →
Golde Fisherman Sandal →
Rachel Heeled Sandal →
Shop all vacation-ready styles →
