Travel expert Samantha Brown shares her top picks for the comfiest travel shoes

"My airport shoes are always a comfy sneaker-like shoe," Brown says. To that end, she's devoted to the FitFlop brand. "They put a lot of technology behind their soles, whether on their boots, sneakers or sandals. They are my go-to across the board!" 

Brown specifically loves the ultra-cushioned F-Mode Flatform sneaker, which has the brand's signature microwobbleboard, an ergonomic midsole that put FitFlop on the map.

But for passing through airport security, it's smart to consider a pair that slips off and on easily, like the stylish Super-Q sneakers, a sock-like, slip-on style by FitFlop that has decorative laces.

This pair bears the brand's patented iQushion midsole, which means they're infused with air foam for ergonomic flexibility and cushioning that quite literally puts a spring in your step. It's a versatile look that'll go with most of the outfits you've packed too.

Related: The 12 best walking shoes for women in 2025, tested and approved

Brown calls Cole Haan driving loafers "classic and elegant" and says the brand uses "a lot of technology in their soles."   

The brand has a slew of options to choose from, but this pair is one of the newest and gives your travel wardrobe an effortlessly sophisticated touch.

They also have a foam-padded footbed — an important comfort feature to look for in shoes that you expect to go the distance (literally and figuratively), and an EVA outsole for grip.

Related: The very best loafers for women, tried and tested by style experts

Another Cole Haan shoe Brown loves is this slip-on ballet flat with non-slip rubber soles. The rounded toe box is a standout feature, while the half-inch heel adds a bit of arch support, setting these apart from most flat ballet styles. 

The elegant gold hardware gives them an upscale look — you won't have to pay upscale prices, though, since they're well under $100.

Brown also loves these woven flats, as the "round toe doesn't squish your toes together."  

There is so much to like about these lightweight, easily packable, highly versatile shoes that come in several fun colors. First, they offer arch support, so you can clock a lot of miles in them. Second, their slim profile looks cute with skirts, shorts, jeans — you name it. 

They're machine-washable, so if they land in a mud puddle, they're easy to get clean. They're waterproof, so if you get caught in light rain, they won't get soggy. Finally, they have a removable insole, so they can adapt to changing conditions as you travel. They're basically like five shoes in one, yet they take up minimal space in your luggage. 

Related: 10 pairs of flats that are just as comfy as sneakers, according to our editors and podiatrists

Brown says this boot is her "destination shoe of choice" when travel calls for a heavier option. "I do still like to look good, and so style is important, but not the most important," she says.  

Thankfully, this Chelsea style delivers on both fronts. The lug sole with a 2-inch block heel and memory foam insole absorbs "the impact of even light walking," while the on-trend style looks great for most seasons and can be worn in a number of ways. 

The boots are available in suede (shown) and vegan leather options in taupe, black or a black and white combo. 

These famously comfortable and breathable slip-on sneakers will be your airport security line MVP, thanks to their easy on-and-off design, says Brown. Plus, the EVA insole and outsole provide superior cushioning — so you'll be delighted to keep wearing them long after you've landed.  

And, of course, their rubber soles make them a great option for just about any terrain you find yourself traversing.