15 Cute Hiking Boots to Get Outdoors in This Season

Functional Fashion

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Hit the trails when the mercury dips this fall and winter, and enjoy the cool mornings and warm afternoons. Whether you’re dayhiking for miles or just spending all day on your feet, a comfortable pair of breathable, waterproof boots can be just as stylish as they are functional, able to transition from cold weather streetwear to off-road companions easily.

Gore-Tex protection makes these boots ideal for the outdoors, whether you’re hiking through surprise spring showers, or traversing muddy trail sections during the fall. Mid height cut, arch support, and a sole designed for trekking make this the boot that can keep up on any adventure.

With pops of accent color and a nubuck leather upper, this sapphire blue boot features stabilizing features, like a deep heel cup, that help keep you stable, so you can prevent ankle twists in a surprise fall, whether you’re trail hiking or pounding the pavement on a chilly day.

Built on a vintage look, these waterproof boots have enough personality to make them stand out, but aren’t so overstyled that you’ll be too worried about ruining them to actually wear them into the rough terrain and nasty weather they’re designed for.

Whether worn to the outdoors or the office, these top grain leather boots are a standout style, marrying form and function in a durable, gorgeous boot. Five color options span from a glossy dress black, to a tan work boot that mimic the look of a steel-toed mens style.

The North Face shoes and boots have a well-earned reputation, and these remastered classics add new tech to vintage style, for a marriage made in heaven. Grippy soles get rave reviews for keeping a solid grip, even on icy sidewalks, and rust-proof hardware serves as a final touch on a well thought-through pair of boots that will last through whatever you throw at them.

Less than a hundred bucks, Columbia’s Newton Ridge boots are the perfect intro pair for anyone who isn’t sure that hiking is really for them. Available in a huge range of sizes, including three width options, the perfect fit is out there for anyone. They also come in more traditional tans and browns, but the blue/cherry combo makes it easy to find them in a flash, whether they’re stashed in a closet, or half buried under sleeping bags on the tent floor.

Serious distance hikers, backpackers, and rangers all know about the durability and support from Asolo boots, but the cheery grape color on their Drifter boots garner so many questions and compliments that the word will soon be out to everyone how great these are.

They’re almost too pretty to get dirty, but the call of nature will just have to be enough to get you over the impulse to keep them clean and perfect forever. Reviewers rave about low or no break-in period, writing that they’ve been worn to the fjords, the rolling green hills of Ireland, and even snowshoeing through Alaska and were the perfect choice of footwear.

At 12oz per boot, Ahnu’s waterproof boots are lighter than a lot of other ladies hiking boots, so you can go further, lighter, and faster. If you’re covering the distance but need a hiking shoe that isn’t a boot, you can also save a bundle with their Air Mesh hikers.

If hiking in your part of the country includes the chance of a surprise snowfall, Columbia’s Snow Boots are an investment piece that will pay back huge dividends. The faux fur collar and 200g insulation combine for superior warmth, with a rating of -25F (-32C). Non-Marking soles ensure that if you have to dash back indoors for gloves, hat, or keys, you won’t pay for it later.

Waterproof but still breathable, these polyurethane-coated nylon boots have microfleece lining for the ultimate fuzzy-slippers experience in these go-anywhere snow boots.

Deep insulation- we’re talking four layers of Sorel’s proprietary ThermoPlus™ felt- make these the most cold tolerant boots on our list, with a rating of -40F. Trek through snow and slush all winter long, with no fear of cold toes in these classic rubber soled boots.

These street-wear approved high top boots are a riff on classic mens styles. Pair with a feminine trench coat, or continue the trend of stealing the best looks from the menswear section and top off with a fun vintage-styled jacket.

A narrow fit that still accommodates room to wiggle your toes, Keen’s hiking boots make even steep ascents a walk in the park. These waterproof boots have mesh uppers for tons of breathability, so even summer hikes won’t leave you with sweaty feet slipping around in your shoes.

These casual-look boots can still perform when called upon, with waterproof leather uppers and an EVA midsole, they’re perfect for the outdoor lifestyle, especially if you’ll be on your feet all day, though they’re not going to be your go-tos for fording rivers or cresting a summit.

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