Stylish Hiking Boots

This article was last updated on April 16, 2022

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Stylish Hiking Boots

When it comes to hiking boots, we don't go by looks alone (as much as we really, really want to). These performance-grade kicks need to hold up to a host of elements — rain, snow, sleet, mud, and more than a little sweat — while supporting our feet and ankles over oftentimes unpredictable terrain. So, when shopping for a pair, there are lots of boxes to check off: are they waterproof? Lightweight? Deeply treaded? Equipped with enough cushioning for a day’s worth of comfy hoofing? And, finally, are they cute?!

Given the sky-high standards required of this workhorse outdoor footwear, there are enough reviews to fill an encyclopedia of online feedback — and we combed them all in order to hunt down the hiking boots with enough bells and whistles to satisfy five-star requirements. In perusing the wares of brands like Merrell, Columbia, Keen, Hoka, and Teva, we looked out for the highest praise and enough R29-approved style points to help them stand out from the pack. 

Ahead, 17 such boots that are supportive AND stylish enough to satisfy the internet’s most exacting shoppers (and hikers).


Stylish Hiking Boots

On Cloudrock Waterproof Boot

The Most Miraculous
There are more proprietary names on this super-engineered speed-hiking shoe than we can count, from MissionGrip (a super-traction-y rubber used for the outsole) to FlexLock (easy-tying laces) to Zero-Gravity CloudTec (cushy, comfy insoles). The mesh upper is waterproof and simultaneously breathable, and the whole shebang is up to 35% lighter than comparable styles — meaning that it can traverse almost any terrain with comfort and ease. Essentially, Cloudrock is a miracle. If you don’t believe us, read what the reviewers have to say.

The Hype: 5 out of 5 stars; 33 reviews on OnRunning

What They’re Saying: “On deserves much reverence and notoriety. Only can imagine the engineering and knowledge of human biomechanics that had to go in this…to have such an end result. I honestly feel lucky to have stumbled upon such an amazing hiking boot. Side note I’m from Florida. Afraid of injury I knew I really needed something next level, especially because I was not used to the kind of rough terrain in Tetons. I feel for an ‘amateur hiker’ these boots alone are going to add miles to my trip for me. I can go on and on but I’ll save you on that. Read the literature. Watch the ads. Everything they say about this boot and their products is absolutely true. The technology is really something you have to feel to believe. The most progressive I’ve seen in awhile truly groundbreaking and innovative. I not only have been completely sold and will only use the Cloudrocks for hiking trips I am completely sold and cannot wait to order my first pair of On Running shoes. I honestly won’t use any other brand from here on out that requires shoes for rigorous activity. OR is my official brand for my feet from here on out. I can’t believe I’ve lived life this long without any of their products. Unreal. I’m beyond impressed.” — Rachel, reviewer

On Running Cloudrock Waterproof Boot, $, available at On Running

Stylish Hiking Boots

L.L. Bean Vista Mid Hikers

Best Vintage Sneaker Style (With Modern Engineering)
Looking for a sneaker-styled boot with all of the advantages of modern hiking footwear technology? Look no further than L.L. Bean’s Vista Mid Hikers. It boasts a waterproof construction and cushy EVA midsole for a supportive fit, while a suede upper gives it that vintage-inspired je ne sais quois.

The Hype: 4.6 out of 5 stars; 4 reviews on

What They’re Saying: “Definitely recommended. These shoes are great! Plenty comfy. Plenty warm (just walked 3 miles in a mix of snow and dirt). Feet are dry. Plus I personally think they are stylish. Good go to kicks for winter when you don’t want to wear a sluggish winter boot. I usually wear a 9.5 in running shoes and a 9 in dress shoes. I ended up with a 9.” — Anonymous, reviewer

L.L. Bean Vista Mid Hikers, $, available at Zappos

Stylish Hiking Boots

Kamik RogueHiker Waterproof Boot

The Warmest
Reviewers find these waterproof leather boots to be super-toasty, thanks to a wool ankle cuff, insulated lining, and sealed seams. Satisfied customers hailing from North America’s coldest climes — Canada, Minnesota, Chicago, Boston — found the boots to chic enough for the office but sturdy enough for light hikes in extreme temperatures.

The Hype: 4.6 out of 5 stars, 47 reviews on

What They’re Saying: “I purchased these boots for a trip to Iceland to replace my current hiking shoes. I wanted something that would cover my ankles and also was waterproof. These were great shoes — comfy, stylish, and held up well for all the walking I did.” — Moonlily, reviewer

Kamik RogueHiker Waterproof Hiking Boot, $, available at DSW

Stylish Hiking Boots

Oboz Sapphire Mid B-Dry Waterproof Hiking Boot

The Most Waterproof
The yuckiest thing about waterproof hiking boots is that they can also keep water in, making your feet awfully clammy as you navigate all of those switchbacks. Luckily, Oboz’s proprietary waterproofing system, B-DRY, lets sweat escape while still keeping moisture out, making these boots waterproof both inside and out.

The Hype: 4.5 out of 5 stars, 114 reviews on Amazon

What They’re Saying: “Not only are these great boots, but Oboz has fabulous customer service. We put a couple of hundred miles on a pair of these; including some boot-challenging time in the Tetons and Zion. They were fantastic – comfortable, supportive, breathable, and solid – they even stayed dry after 1/2 hr climbing an active creek bed when other brands soaked their owners.” — TD Cook, reviewer

Oboz Sapphire Mid B-Dry Waterproof Hiking Boot, $, available at Amazon

Stylish Hiking Boots

Eddie Bauer K-6 Boot

The Most Untouched By Time
Talk about a time-tested style — Eddie Bauer made this exact boot in 1964, and its popularity is unchecked in the present day. We can see why — behind the quaint leather exterior hides a workhorse shoe, with a stabilizing heel cup and superior forefoot support, and a Vibram outsole.

The Hype: 4.6 out of 5 stars; 36 reviews on

What They’re Saying: “I wasn't sure about the white soles at first but I LOVE these. They have a really retro feel to them, are fully lined, have a comfortable sole, and are waterproof. They are roomy enough for thick socks, so are good for hikes in cold or wet weather. They are a bit on the heavy side, but not to the point of being unpleasant.” — Cookie Munster, reviewer

Eddie Bauer K-6 Boot, $, available at Amazon

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