5 Best Men’s Travel Shoes: Your Buyer’s Guide

mens travel shoes


It’s simple: when you talk about men’s travel shoes, you’re talking about good walking shoes. When you consider the buy on the travel shoes, it breaks down to three things:

  • Issue #1 – they gotta be comfortable.
  • Issue #2 – they take up a lotta room in the suitcase.
  • Issue #3 – they need to be versatile.

Travel means you’re going to be doing more walking than usual. You’re not at work, you’re not home on the couch. You’re playing tourist (trying to become as cool as a local) and seeing the sights (something locals don’t even do). You don’t want your sore feet to be anywhere near the vacay itinerary.

Travel also means you need to pack efficiently. Because men’s feet are bigger, they create a limitation women don’t face (as much): the shoes crowd the bag. Ergo, travel shoes does not equal a big fat pair of boots. (Unless you’re going to big-fat-pair-of-boots-land and you’ll need them.)

And travel also means you’re going to be looking good, which translates to wearing different outfits. You need shoes that work well with a variety of fits.

Each of these pairs are comfortable enough — they’re good walking shoes, for crying out loud — that you’ll be able to rock them, look good, and forget all about them so you can focus on that vacation.

What are the Best Cool Men’s Sneakers?

1. Skechers Performance Go Walk Max Sneakers – $19.26 and up (depending on size/color)

skechers performance mens go walk max sneakers


When it comes to a “walking vacation,” these men’s travel shoes might be indispensable. Not only do they have a look that works with shorts, jeans and chinos, they’re also maximally comfortable.

The pair is from Skechers’ “Performance” line of shoes. They’ve got the brand’s latest midsole cushioning (5GEN), which Skechers calls “parametric cushioned” for added comfort. The insole features Skechers Goga Max technology, which is designed for cushioning and support.

The upper is all mesh and it’s been designed to naturally expand with your foot while you walk. (Good to know while you’re visiting the third museum of the week.)

In addition to all of this, these will pack very well in the bag because they’re flexible and super lightweight at just around six ounces.

Shown in charcoal, the shoes are available in six different colors (color availability changes periodically).

Buy the Skechers Walk Max Sneaks here.

2. Olukai Moloa Slip On Loafers – $87.50 and up (depending on size/style)

olukai mens moloa loafers


Olukai is the brand with the island vibe, which accounts for the name Moloa. They make a wide range of shoes and I think it’s safe to say that they’re all comfortable. (Olukai provided me with a pair of its Kahu Laces and I know from experience about the high degree of comfort.)

The Moloas are a great option because they’ll work very well for walking and for edging up into a little bit dressier category. They are, though, very versatile because they can be worn casual or dressier.

The upper is all leather, which is water resistant, and they feature hand-sewn whip stitching. There are small goring sections (expandable, elastic fabric) on the vamp, making them easy-in, easy-out.

The sole is an all-weather outsole that has non-marking traction pads. Another great thing about these is the heelstay: it’s very flexible and malleable so if you want to turn the shoes into slides, just step down on the heel and voila!

Shown in “ray/toffee” color, the shoes are also available in black/toffee.

Buy the Olukai Moloas here.

3. Blundstone Summer Chelsea Boots – $150

blundstone suede summer chelsea boots


I have written about these boots before and I’m gonna keep preaching because they are, probably, the most comfortable shoe I’ve ever worn. (Blundstone provided me with a pair and I became an instant believer.) They definitely belong on a list of the best men’s travel shoes.

When I was recently on vacation in London — running all over the place to eat and drink and eat and drink some more (and maybe some museums) — these were one of my go-to pairs because they “worked” all day and into the night.

These are the company’s lightest weight boots — Blundstone calls them “summer boots” — with Blundstone’s Featherflex soles and a leather upper that features a reduced height through the ankle.

According to Blundstone, the summer boots line “was designed for comfort and shock absorption, with added durability to the sole tread for improved wear and tear.” They’ve got two logoed pull tabs, one in front and one in back (the tabs are conveniently long, making the boots even easier to get on).

Besides all the comfort, they’re Chelseas. They just look dang great. We’re showing them in Suede Olive but they are available in black and other colors.

Buy the Blundstones here.

4. Born Jib Leather Lace Up Sneakers – $49.99 and up (depending on size/color)

born mens jib leather sneakers


Born is a shoe company that has, as its mission, a focussed emphasis on comfort. While I’ve never owned these shoes, I’ve owned two other styles from Born and they are fantastic.

The Jib is a “relaxed” leather sneaker, according to Born, that has extra padding around the ankle and a cushioned insole for comfort to “all areas of the foot.” The footbed is removable, which is a plus in case you’re a foot-sweater.

Shown in “cuero” color, the Jib is available in seven different colors (color availability changes periodically).

Buy the Born Jibs here.

5. Rockport Dressports 2 Go Lace Ups – $54.12 and up (depending on size/color)

rockport mens dressports 2 shoes


Rockport is, of course, the company that was created with the sole intent of making good walking shoes. Fortunately for us, they’ve got the Dressports 2, which are also focussed on being dressier than the typical walking shoe.

These do feature a leather upper and a synthetic sole. The sole is in a contrasting white, which provides an on-trend, modern look. The welt stitching (where the upper meets the midsole) is a great detail.

The heel cup is EVA (a type of synthetic rubber designed for softness) and the forefoot features foam cushioning. The collar on the shoes is padded and the lining is textile.

Shown in “new caramel,” the shoe is also available in “castlerock” (a medium grey tone) and “rocksand” (a very light greyish/brown).

Buy the Dressports 2 Go here.

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