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World of Software > News > I think ugly shoes are the comfiest — and these are the 3 you need to buy
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I think ugly shoes are the comfiest — and these are the 3 you need to buy

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Last updated: 2025/09/18 at 12:41 PM
News Room Published 18 September 2025
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My priority when buying new clothes or footwear is always how they will look. This is only natural and a product of the world we live in today, where beauty is often rewarded. And yes, this rule even goes for shoes.

I have been known to absolutely destroy my feet with blisters in hiking boots and Doc Martens, while crippling my toes in high heels, all in the name of a good outfit. Beauty is pain, right? But after years of this, I’m fed up with walking a day in good-looking shoes only to hobble around for the next week as I attempt to regain the use of my toes.

So I propose this: everyone should have at least one pair of ugly shoes.


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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.

Icebug Rover RB9X GTX


Icebug Rover RB9X GTX in green with boa lace

(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.

Keen Zionic Mid Height Waterproof


Green Keen Zionic Mid Waterproof hiking boots for women

(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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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.

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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