My 6 Favorite Boots for Traveling In and Walking All Day

Most guys who like boots like them because they are tough, durable, sturdy, and built with thick leather that ages well. Unfortunately, those aren’t the qualities that you want in footwear when you’re traveling.

Travel boots are a different genre: with all the metal detectors, air travel, airport walking, and sightseeing, I look for boots that are lightweight, versatile, flexible, grippy, water-resistant, and comfortable for walking all day.

But you might have different priorities, so I’ve chosen boots that score slightly differently in those categories — this way, you’ll find something that works for you and the trip you’re planning.

That said, the number one requirement everyone told me they have with travel footwear is “easy to take off for metal detectors”, so I’m really emphasizing slip on boots here.

My Criteria for Best Travel Boots

In rough order of importance (to me, personally), here’s the criteria I prioritize:

• Easy on and off
• Lightweight
• Flexible
• Versatile
• Comfortable (little to no break in)
• Decent traction
• Decent water resistance

To make this list as useful as possible, I looked all over Reddit and other forums for what other people look for in their travel boots, and the priority was always “easy to take on and off.”

So, everything on this list is laceless. This way, you can breeze through airport security and kick them off on the plane (and slip them on to go to the bathroom) with minimal fuss.

I also want lightweight boots, because every ounce counts when you’re traveling. I want boots with a decent grip and a reliable outsole for traction on wet city sidewalks, cobblestone streets, or light trails.

Water resistance is a must, but that doesn’t mean waterproof. I always prioritize boots that can be resoled, partly because of the longevity, but also because if they can be resoled, then they’re also going to be sufficiently water resistant to handle puddles.

But travel boots should also be versatile. It’s unlikely that you’re traveling with multiple pairs, so I want the functionality to be balanced with good looks that pair well with my favorite jeans and with smart chinos for going out.

Lastly, you don’t want to be breaking in boots when you’re traveling. And since you’re probably reading this because you’re looking for boots for an upcoming trip — meaning they’ll be new when you leave — it’s important that the boots don’t have the kind of super robust construction and thick leathers that make them blister factories for the first few weeks of wear.

Sounds impossible? Nah, I know a lot about boots. You’re in good hands, and I’ve made this list to feature a range of different boots with different strengths.

1. The Sneaker Boot: Luca Terra Sneaker Boots

• Good entry level boot for guys used to sneakers
• Not resoleable, but very lightweight and no break in
• Stitched cupsole has good water resistance
• Cushy Lactae Hevea natural rubber outsole
• $215

The first entry is a product I never thought I would enjoy: sneaker boots. I won’t say Luca’s Chelsea is the most versatile boot in the world, but it’s a good starting point for a lot of guys, especially the kind searching the internet for travel boots: compared to traditionally made boots, Luca’s is lighter (the lightest on this list; I weighed them), cushier underfoot, easier to break in, and cheaper.

It’s true that it’s not resoleable, but because this has a stitched and glued cupsole construction, it’s still far more durable and water resistant than your average sneaker.

While some guys like boots for their stability, others prefer softness underfoot, and Luca’s boot excels in that arena. That has a lot to do with their Lactae Hevea soles — a really premium rubber that’s also on my $800 luxury sneakers and my antelope suede boots from a traditional workshop in Maine. It’s all-natural, harvested from rubber trees in France, and considered top-of-the-line for a rubber sole.

What I like

• There are no laces to mess with; the Chelsea design means you can slide these on and off in seconds at TSA checkpoints or during the flight.
• It is noticeably lighter than a resoleable boot; it won’t drag you down during long days of walking and is easier to pack in your suitcase.
• The cushy insole and a Lactae Hevea natural rubber outsole are springy and shock-absorbing.
• There’s minimal break-in; the upper and leather lining are soft from the get-go.
• A clean, minimalist look; you can’t wear it with a sport jacket, but it can go smart casual.

Downsides but not dealbreakers

• No half sizes, they might be tough to get a good fit; I’m a half sized, sized up, and it was fine. The low instep and pliant construction lower the risk of a loose fit, but it’s not risk-free.
• It’s less water resistant than a Goodyear welted boot, though it will handle light rain.
• Fundamentally casual. The soft sole and suede give it a more laid-back vibe.
• Not resoleable, though the cup sole is both glued and stitched, making it much longer lasting than regular sneakers.

2. Most Versatile: Thursday Cavalier

• Sleek silhouette dresses up and down easily
• Resoleable Goodyear welt
• Range of leathers and widths
• Great value
• $190

This is the boot for guys who want something that’s more versatile and long-lasting than a sneaker boot; the Cavalier is Goodyear welted, so it’s more water resistant and durable, yet it’s also easier to dress up.

This brand sells four kinds of Chelseas, and I almost put their best-selling Legend Chelsea on this list because that one has a really grippy sole. But even though the Cavalier’s main downside is the so-so grip, it’s much lighter weight and more versatile than the Legend — it’s almost as light as the Luca, which is bonkers for a Goodyear welted boot.

I think it’s the most versatile boot on this list. Depending on what you need and your style, you can get it in more casual (suede) or dressy (smooth black) leathers. Personally, if I’m trying to get one boot to do it all, I’d get the dark brown suede they call “Chocolate.” Brown suede can easily go from jeans and a t-shirt to slacks and a button-down. 

I actually did a capsule wardrobe article a while back where I picked three kinds of footwear to last you in just about any situation, and this was the one boot I chose. The only downsides are that it’s a bit slim to wear with really loose pants, and the grip is just okay.

What I like

• Better shock absorption and less of a break in than comparable boots, thanks to thinner uppers and Poron insoles.
• Good range of leathers and widths.
• Can pass as a dress boot but looks equally at home with jeans and a leather jacket.
• Made with a 360° Goodyear welt construction, yet it’s very light and flexible.
• $190 is a remarkable price for how much boot you get.

Downsides but not dealbreakers

• Thinner leather and less substantial feeling than traditional boots, but that’s the whole point here — that’s saving you both money and from a tough break in
• Strictly an urban boot, given the not-super-functional outsole.
• Slim build makes it best for straight and slim fit pants, not so great for wide leg fits.

3. Casual: Red Wing Weekender

• Very casual and probably the most “rugged” boot on this list
• Construction is a good balance of resoleable and lightweight
• Comfortable wedge sole
• Made in America with American leather
• $260

Red Wing’s Weekender Chelsea boot stands out on this list for its extra tough leather, for being made in the USA, and for its unusual kind of stitchdown construction that makes it resoleable, water resistant, and lightweight.

I think it’s the most underrated boot from this brand. Most Red Wing Heritage boots are built more like traditional heavy work boots, but this was made to be more of a “leisure boot”: with stitchdown construction and an extra-thin crepe rubber sole, it’s surprisingly light and easy to wear.

With its work boot leather and contrasting sole, this is less versatile and more casual than a lot of other boots here, even the Luca. But it’s really tough, the leather will age beautifully, and it doesn’t give any of the “dainty” vibes that some Chelseas can.

What I like

• Famously tough leather; thick and oil-tanned, it’s made for longevity and will age beautifully, without the usual brutal break-in you can have with other Red Wing boots.
• A thin, lightweight outsole gives good groundfeel and softness, especially for a Red Wing
• Easy to slip on and off, thanks to the elastic side panels and pull tabs.
• Resoleable yet lightweight thanks to the stitchdown construction and thinner sole.
• No steel shank, so it’s easy to wear through metal detectors.

Downsides but not dealbreakers

• Less stability than most heritage boots; due to the softer sole and lack of shank.
• This boot leans rugged-casual; with the dynamic leather and contrast sole, it’s hard to even dress up to smart casual.
• Low instep; this worked well for me, but if your instep is more prominent, these might not fit you

4. Waterproof: Ariat Wexford

• Rare combination of fully waterproof and fully stylish
• A lightweight shank helps with stability without tripping metal detectors
• Inexpensive
• ~$200

Next up are the stylish but waterproof Wexford boots. Is it the smartest boot in the world? No, but if you want travel boots that are really ready for the outdoors — fully waterproof and plenty grippy — the Wexfords will accomplish your goal without looking too outdoorsy.

These are the best looking waterproof boots I’ve ever seen. They tend to be really bulky to accommodate a waterproof membrane, and they tend to be made for jobsites and look like it — but the Wexfords look like regular boots.

They’re still firmly casual, don’t get me wrong. But you won’t look like you stepped off a Midwestern farm if you wear them with jeans on European cobblestones.

The downsides are that they’re the heaviest on this list and cannot be resoled. You can almost never resole a waterproof boot, though. So, if that doesn’t bother you, it’s under 200 bucks and very functional.

What I like

• Fully waterproof, but doesn’t look like it.
• It has a supportive fiberglass shank that’s lightweight and TSA-approved.
• Grippy sole is functional but not overbuilt.
• Around $180-$200, the Wexford is priced accessibly, especially for a fully waterproof, well-made boot.

Downsides but not dealbreakers

• Not resoleable, which is par for the course with waterproof boots.
• Not that versatile; it’s a good-looking casual boot, but it’s a casual boot.

5. Side Zip: Beckett Simonon Easton

• The dressiest boot on this list
• Blake stitched construction is lightweight, flexible, and resoleable
• Sleek leather sole
• Made to order = long wait time
• $239

Instead of a Chelsea, this is an underrated style that’s just as easy to get on and off: the side zip boots from Beckett Simonon called the Easton.

They are Blake stitched, so they are resoleable, but very light and flexible. They are a bit less water-resistant than the others here, but they’ll get you through a light rain without a problem, certainly more easily than canvas sneakers.

And it looks really, really smart. Without the elastic goring of a Chelsea, it’s easier to dress these up for a nice dinner with trousers and a jacket. You could say the same for Thursday’s Cavalier, to be fair, but some folks just don’t think Chelseas should dress up.

Some people complain that a zipper is a breakable part of a boot, which is fair. But it’s easy and cheap for a cobbler to fix it if that happens, so you might find the Easton’s advantages to outweigh its downsides.

What I like

• Arguably the dressiest boot on this list, smooth leather and minimal seams make for a real clean look.
• Little break-in; the combo of Blake stitch and leather sole means that new Eastons shouldn’t punish your feet.
• Blake stitch construction, gives a good balance of resoleability and comfort.
• Leather outsole has a lot of underrated benefits, like breathability and comfort
• $239 is inexpensive for what you get

Downsides but not dealbreakers

• You’ll wait 2 or 3 months for them to arrive; that made-to-order model is what keeps the price down.
• These aren’t boots for going off-road; the leather sole and Blake build aren’t made for hard wear.
• The zipper is a breakable part; one day far in the future, it might break, and you won’t be near a cobbler.

6. Winter: Allen Edmonds Tompkins Shearling

• Shearling lined for added warmth
• Storm Goodyear welted; great blend of water resistant and resoleable
• Made in USA
• $495

Allen Edmond’s Tompkins is great if you’re heading somewhere cold: it’s fully lined with shearling wool for extraordinary warmth, it’s resoleable and water resistant, it’s made in the USA, and it’s one of those funky side zip boots. They even sell a version without the shearling if you like everything else about it.

While I think the Easton is a great option if you might dress up a bit, the Tompkins leans a little more Western, especially with that extra rugged (and waterproof) leather.

These are more expensive, heavier, and stiffer than anything else on this list. But the upsides will be very valuable to the right guy.

What I like

• Warm shearling lining is great for cold weather, and these look so much better than most winter boots.
• Convenient side zip construction is great for winter boots, especially if you hate de-gloving to tie a loose lace.
• Unusually sleek sole for a winter boot, these don’t have the normal thick lugs.
• Made in Wisconsin for a home field advantage.
• Storm welted; an especially water-resistant kind of Goodyear welt; these will last through as many soles (and storms) as you can throw at it.

Downsides but not dealbreakers

• Not for warm weather, unless you want that unlined version.
• Just two casual leathers to choose from
• Expensive
• Stiffer and heavier (but tougher!) than the rest of these boots

Wrapping Up

You may not have realized there were so many options out there for slip on boots, but I think that’s a pretty good selection of great travel options! I gave you some really casual ones, more functional waterproof ones, dressy, cold weather, the lot. Go me. Good list, Nick.