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I think ugly shoes are the comfiest — and these are the 3 you need to buy

AnyFans 2025-09-27

By Ashley Thieme

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I have compiled a list of some of my favorites that I think are incredibly comfortable, and I’ll share a bit about why walking comfortably is so beneficial for you.

Keen Hyperport H2

(Image credit: Tom’s Guide)
The Keen Hyperport H2 sandals are the epitome of gorpcore: high-performance clothing that can double as streetwear. While these are shoes I wouldn’t normally be caught dead in, they are sort of… charming.
And for me, that charm comes from how comfortable they are. We got to test them here at Tom’s Guide, and when I tried them on, it was like walking on air. The adjustable strap of the shoe also makes them feel very secure. I would honestly walk for days in these shoes.

Keen Hyperport H2: $119 at Amazon
Self-proclaimed as “The world’s ugliest sandals”, the Keen Hyperport H2 shoes are a dream on a summary walk. They are hiking sandals, so they are pretty sturdy, but they have cutouts on the side to keep you cool. They are designed for water, making them perfect for river trails as well as everyday walking adventures.

Icebug Rover RB9X GTX

(Image credit: Tom’s Guide)
These are more of a daily walking shoe. But why are walking shoes so ugly? I have these shoes in green, and while they certainly blend in with the mossy floor of the woods where I go trail walking, they’re not my usual bag.

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But I am actually willing to throw style out of the window when it comes to wearing these because, frankly, the comfort is unmatched. The Boa adjustment on the lace closure of the shoes means they are easy to adjust. So when my feet inevitably swell after walking for hours, I can adjust the fit with minimal fuss.
These currently serve me well on light trail walks at the Country Park, but I’d spring for something with ankle support for rougher terrain, like the Keen Targhee IVs I own or the Zionic Mids below.

Icebug Rover 2 RB9X GTX: $199 at Amazon
They are a little on the expensive side, but the Icebug Rover RB9X GTX offer incredible support to the soles of your feet to support you on all adventures. From light trail hiking to city exploring, these shoes have you covered for all-day long comfort.

Keen Zionic Mid Height Waterproof

(Image credit: Tom’s Guide)
Just like their sandals, Keen knows how to make an ugly boot. But I should say, I usually love Keen boots. I have a pair of the Targhee IVs I mentioned earlier that go perfectly with my hiking gear. But the same can’t be said for the Keen Zionic Mid Height Waterproof hiking boots — beauty is in the eye of the beholder, but these boots are far from pretty.

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Dear haters, you’re wrong — the ‘ugliest sandals in the world’ are actually the hiking sandals I was missing all along

I would walk 500 miles and I would walk 500 more in these Keen boots — and they’re currently 40% off

I hike every weekend — here’s how to break in your boots and avoid getting blisters

But once again, the performance is far too good to pass up based on style alone. The waterproofing means they are quick to dry after rainy hikes, but the composition of the soles means there is complete support at the soles of the feet, as well as around the ankles.
I’m pretty clumsy. Add hiking into that, and you are pretty much asking for disaster. However, the support from these shoes made the rocky terrain a breeze.

Keen Zionic Mid Height Waterproof: $169 at Amazon
Keen knows how to make a comfortable shoe, and the Zionic Mid Height Waterproof is no exception to that rule. The Cushioned insoles are springy, so they can cope with any terrain, and the grippy outsoles are perfect to stop any slipping and sliding in wet weather. I don’t love the design of these, but they have too good a performance to pass up.

Why walking comfortably is more important than walking in style
Believe it or not, making sure you have the right footwear every day is essential for overall health. I certainly notice that when I wear shoes that aren’t the comfiest for a while, it will take me longer to bounce back from dealing with back pain and headaches.
An uncomfortable pair of shoes can mean that your gait changes — basically you walk funny to compensate for your discomfort. Healthline states that this can lead to tension in the back and neck, which leads to tension headaches (and don’t I know it). Wearing uncomfortable or ill-fitting shoes can also lead to problems in your legs, such as plantar fasciitis!
I promise you’ll be thanking yourself for going with a comfy pair of shoes — you’d rather be doing that than cursing yourself later on for not doing so. Looking after your feet really does mean looking after your whole body.
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Ashley Thieme

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Staff writer, Reviews

Ashley is a staff writer on the the Reviews team at Tom’s Guide. She has a master’s degree in Magazine Journalism from Cardiff University and a BA in Journalism, Media and Sociology. She has written for titles including Women’s Health UK, writing health and wellness stories, and Virgin Radio UK, specializing in entertainment news and celebrity interviews. She has reported on a variety of topics including music, literature, motorsport, entertainment and health, and has her own bookish newsletter, Ashley’s Reading Nook.She has previously reviewed live music events, books, and wellness products but finding the best way to listen to new music releases is essential for Ashley, so discovering the top audio equipment on the market is what she does best.When she is not testing out the latest tech, you can find her either curled up with a cup of tea and a good fantasy novel or out hiking.

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