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Shoes are the reason people check a bag.
Not the clothes. Clothes squash. Shoes don’t. Three pairs will eat more of a carry-on than a week of outfits, and every pair after the third is the one that puts you at the airline counter with a credit card out.
So the question isn’t which shoes. It’s how many, and what each one has to do.
My answer has been the same for years. Three pairs, and every pair has a job. It’s the shoe half of my free guide Lisa’s Carry-On Only System, and shoes are what you email me about more than almost anything else.
The three jobs
The walking pair. The one you’re in for eight hours on cobblestones. This is the pair that decides whether day three is any good.
The nice pair. The one that works at dinner, in a church that has a dress code, or anywhere you’d feel underdressed in sneakers.
The wet pair. The hotel shower, the beach, the pool, the boat. Something that gets wet on purpose and dries by morning.
If a pair doesn’t do one of those three jobs, it isn’t coming.
Why your feet hurt on day three
The shoe question I get most isn’t which brand to buy. It’s some version of “will these work on the cobblestones?”
I’m going to disappoint you slightly. Cobblestones are not really the problem. Uneven stone is a nuisance. Distance is what wrecks your feet.
At home you walk from a car to a door a few times a day. On a good trip you’ll do eight or ten miles without noticing, on surfaces that don’t give at all, in shoes you last wore to the grocery store. Day one is fine. Day two is fine. Day three your feet file a complaint, and by then you’re committed.
So cushioning, not tread. This is the one people get backwards. You don’t need grip for a European city, you need something between your heel and a thousand-year-old street. Tread is for mud and trails. Miles of stone is what a city trip actually is.
And break them in before you go. All of them. New shoes on day one is the most common way people ruin a week, and if you’re wondering whether you can push through it: wet feet are annoying, but wet feet in a shoe you’re also breaking in is a bad day.
The walking pair
This is the one worth spending money on.
Mine is a Cole Haan Grand Crosscourt, a plain white leather sneaker. It walks all day and it still looks right with a dress at dinner, which is why it beats a running shoe for me. White leather cleans up with a wipe. A mesh sneaker that’s been through four cities looks like it’s been through four cities.
If the trip is wet, I swap it. My rain pair is the On Cloud 5 Waterproof, and I mean actually waterproof rather than waterproof until it rains. They held up walking the Camino de Santiago in real rain.
Matt wears HOKAs and nothing else anymore. I tried both and preferred the Clouds, which is the whole point. Feet are personal, and this is the part of the list where you should trust your own over mine.
If a sneaker isn’t sturdy enough for what you’re doing, there’s a whole category of proper walking shoes built for real miles. My mom, who walks as often as she can because moving is the best therapy there is, swears by her Merrells.
Whatever you land on, put merino wool socks with them. Wool still insulates when it’s damp. Cotton very much does not.
The nice pair
The mistake here is packing something you’d wear to a wedding. You’re not going to a wedding. You’re going to dinner after walking nine miles.
Mine is a Rothy’s flat. Comfortable enough to walk in when the day runs long, dressy enough for dinner, and machine washable. The whole shoe, in the machine.
The test for any nice pair: could you walk a mile in them without planning around it? If not, it’s a fourth pair and you’re carrying it for nothing.
The wet pair
The cheapest and least glamorous thing in the bag, and the one I’d replace first if it went missing.
Mine is a pair of REEF flip flops. They weigh nothing, they dry instantly, and they mean I never stand barefoot on a hotel shower floor.
If you’re walking any distance in them, a sport sandal with a strap goes a lot further, because the strap keeps the shoe on your foot. On a beach week I’d take either. On a week where wet means the shower and nothing else, take the flip flops and give the space back to something else.
What I don’t pack, and this one is firm
Hiking boots.
I’ve stopped putting them in the app I built and I’ve stopped putting them in my bag. If you’re doing a serious multi-day hike with a heavy pack, ignore me and take your boots. You already know what you need. For everyone else, a trail runner does the job for a fraction of the space and weight.
I looked into this properly before I made it a rule, and women over forty prefer trail runners to boots by a wide margin. They walk, they handle a real trail, and they don’t make you look like you’re headed somewhere serious when you’re going to lunch afterward. A trail shoe with a lugged sole and some toe protection will take you up most of what you’re likely to walk up.
One more thing on trail shoes: a breathable one beats a waterproof one on a long trip. Once water gets in over the collar of a waterproof shoe, it stays in for days.
The exception, and it’s the question I get most
What about the hotel gym? What about pickleball? Walking shoes are not court shoes, and people are right to ask.
The rule is the same one as the boots. If you genuinely need a sport-specific shoe on a trip, it becomes one of your three rather than a fourth pair. And you wear it on the plane rather than packing it.
What usually gets bumped is the nice pair. That’s a real trade and you should make it on purpose rather than discover it at the hotel.
Treadmills and stationary bikes don’t need anything special. A cushioned walking shoe handles both. It’s only court sports, anything with hard lateral movement, that need their own shoe.
Wear the biggest pair on the plane
Whatever the bulkiest of your three is, that’s your travel-day shoe. It’s free space, it’s the pair you’d least want to lose if a bag went missing, and airplane floors are a good argument for closed shoes anyway.
Slip-ons make security faster. Anything you have to sit down to lace does not.
Which is why the walking pair usually travels on my feet rather than in the bag. The rest of what I carry is in my free guide What I Actually Travel With.
Which three depends on the trip
The three jobs never change. Which shoes fill them absolutely does. Your September in Scotland and my week in Greece are not the same trip, and a list like this can only take you so far.
I’d been answering those emails one at a time for a couple of years when it occurred to me that the answer always follows the same path. So I built the path. Answer a few questions about the trip you’re actually taking and it fills your three slots, with a reason on each one. I’ve marked which pairs I own and wear myself and which ones I’d recommend but haven’t put on my own feet, so you can tell the two apart. If you’d rather just see what I carry, here are the three pairs I travel with most of the time, and here’s Matt’s list.
Frequently asked questions
How many pairs of shoes should I pack? Three, and one of them is on your feet. Walking, nice, wet. A fourth pair is almost always a second version of one you already have.
What if I only want to bring two? Drop the wet pair and buy cheap flip flops at your destination if you need them. Don’t drop the walking pair to save space, and don’t make one shoe do the walking and the dinner unless it genuinely does both.
Are white sneakers a bad idea for travel? No, as long as they’re leather. White leather wipes clean in about ten seconds. White mesh does not. It’s the material rather than the color.
Do I need waterproof shoes? Only if you expect real rain for several days. Waterproof shoes are warmer and less breathable, and once they’re wet through the top they stay wet. For a normal trip with a normal chance of showers, a shoe that dries fast beats a shoe that keeps water out.
What about hiking boots? Not unless you’re doing a serious hike with a heavy pack. A trail runner covers almost everything most of us actually walk, and it weighs and packs like a sneaker.
Can one pair do all three jobs? No. The closest is a clean leather sneaker that handles walking and passes at dinner, which covers two of the three. Nothing sensible does walking and wet.
How do I break in a new pair before a trip? Two weeks of normal wear, including at least one long walk in the socks you’ll actually travel in.
