Stylish Hiking Boots: Bridging the Gap Between Fashion and Function

Stylish hiking boots
Russell McCarty
Written by Russell McCarty

If you ask most hikers what their main concerns are when they set off on a new adventure, you’ll likely get a small pool of similar answers: the weather, trail conditions, that creaky old knee injury that pops up at the most inconvenient times.

What you probably won’t hear are concerns along the line of “Yeah, I’m a little preoccupied about the possibility of an afternoon thunderstorm slowing us down, but what I’m really worried about is how I look. Is my hair okay? My makeup? Do you think I should wear more stylish hiking boots? Or a more flattering hat? I mean, I know I look cute, but do I look hiking cute?”

This isn’t to say that hikers don’t care about their appearance. Of course they do! After all, we all know that the minute you don’t expect to run into another living soul is the precise moment your smoking hot ex comes wandering into the frame, be it at midnight in the potato chip aisle of the grocery store or at a random point on a desolate mountain trail.

Women's hiking boots

But more than looking-good-to-make-him-regret-dumping-me insurance, we all just like to look our best because it makes us feel our best. And part of looking and feeling our best means selecting clothing and footwear we like — something that can be a challenge for hikers who place high value on the performance of their gear.

Sure, that baby-soft lavender fleece is pretty, but how does it hold up against biting late fall breezes? Will it maintain an optimal core temperature, or just go really well with my blue lips when the park rangers have to rescue me from the brink of hypothermia? You can certainly understand the valid concerns here.

Happily for everyone, today’s manufacturers have provided us with a variety of fashionable yet functional choices to make us look fabulous on the trail. One of the most exciting options to explore is footwear; gone are the days of clunky clodhoppers devoid of any finesse or flair. There are now a wealth of stylish hiking boots to choose from, and we’re going to take a closer look at some of the most popular pairs available.

Hiking boots for men

Before grabbing your credit card and going hog wild on all the fashionable hiking boots to be found, you need to educate yourself on some ground-level hiking boot basics to ensure you won’t be totally blinded by the bells and whistles of today’s stylish options.

Even if you already consider yourself pretty knowledgable when it comes to selecting trail-friendly footwear, it doesn’t hurt to brush up on the ins and outs of hiking boots before sinking your cash into a new pair.

Types of Boots

Day hikers/Trail boots

If you’re headed out for a breezy day on the trail or a short backpacking excursion with a light pack, these mid- to high-cut boots will do the trick. They often sport a combination of fabric and leather but usually aren’t waterproof right out of the box, so you’ll have to take a few extra precautions if there will be a lot of wading in your future.

Hiking boots for women

While these boots definitely offer more durability and traction than your running or walking sneakers, they lack the support needed to keep you stable on under a heavy pack, so be mindful of your cargo. Day hikers typically don’t require much breaking in before they’re ready to go.

Backpacking boots

These boots will happily help you bear the brunt of a heavier load on more challenging turf, with a high, above-ankle cut for optimal support. Some styles are waterproof, while some are purposefully porous to allow for better air flow during hikes in hotter climes. Thicker, stiffer mid-soles protect your feet from rocky terrain, but still allow for plenty of flexibility.

Off-trail boots

The name says it all! These beauties will take you off the beaten path, giving you sure-footed security with above-ankle support and rigid midsoles. Off-trail boots are usually constructed with full-grain leather (more on that later), and require quite a bit of breaking in before the sole and heel cup are soft enough for multi-day, heavy load hikes.

Woman wearing hiking boots

Some varieties allow for the addition of crampons (lightweight steel or aluminum traction clamps that improve grip on snow, ice, or steep inclines). Most off-trail boots are waterproof thanks to minimal seams and all-leather uppers.

Mountaineering boots

If steep terrain is your thing, these heavy-duty, crampon-friendly, high-load-bearing boots are for you. With their minimal seams and full-grain leather, they are fully waterproof and usually come with an extra layer of insulation.

Their above-ankle support and rigid build make them a poor choice for regular trail trekking, but the perfect pair for short-stride hiking on steep slopes. Expect to spend a good amount of time breaking in these boots before attacking any mountains.

Hiking Boot Construction


The uppers—the part of the shoe that covers the foot—are obviously a critical component when it comes to hiking boots and their prime directive of keeping you upright with your extremities intact.

Leather hiking boots

Here are a few typical examples of typical hiking boot uppers and how each affects the performance of the boot.

  • Full-grain leather: With apologies to the cows, there is nothing that beats full-grain leather when it comes to water resistance and durability, although it does require generous break-in time.
  • Split-grain leather: This material is the result of “splitting away” the rough, inner part of the cowhide from the smooth outer layer. Split-grain leather is used in conjunction with nylon or mesh to produce a lightweight, well-ventilated, and more affordable boot. Split-grain uppers offer less water resistance, however, and aren’t quite as resilient against the bumps and scrapes of rough terrain.
  • Nubuck leather: Often confused with suede, Nubuck leather is actually a full-grain leather that is buffed and brushed to yield a suede-like appearance. As a full-grain leather, it is water- and abrasion-resistant, but requires ample break-in time.
  • Synthetics: This family is commonly found in boot construction, and includes polyester, nylon, and synthetic leather. Synthetic uppers make for a lightweight, easily dried, and more affordable boot that takes much less time to break in. They require more stitching, however, and this typically causes the boot to show wear much sooner than with leather.


Midsoles are that all-important ingredient in boot construction that cushions your foot and protects it from shock. There are two common midsole materials:

  • Ethylene vinyl acetate (EVA): Very soft and very affordable, EVA comes in a variety of densities to provide more support where necessary.
  • Polyurethane: This sturdier, firmer material is a go-to for midsoles in heavy-duty off-trail boots and mountaineering boots.


Rubber is the rule when it comes to hiking boot outsoles, and some manufacturers add carbon to increase stiffness in mountaineering or off-trail boots. The outsole characteristics you’ll want to keep in mind while browsing are:

  • Lug pattern: A boot’s traction comes down to the lugs, or bumps, on the outsole. Deeper, fatter lugs will provide good grip on heavy duty boots, and widely spaced lugs made it easier for mud to dislodge from the bottom of the boot as you travel.
  • Heel brake: Hiking boots have an easily identifiable heel area, separate from the arch and front of the boot. A sturdy heel brake protects against sliding on steep surfaces.

Hiking Boot Fit

A hiking boot should fit snug—but not tight—to your foot, while still allowing your toes to wiggle freely. Always try on boots at the end of the day when your feet are at their fattest (no offense; everyone’s feet swell over the course of the day, and yours most certainly will after a day of hiking), and be sure to wear the socks you’d normally wear on the trail.

Winter hiking boots

Take your boots for a little spin around the store, going up and down stairs and moving from sitting to standing and back again (why not throw on a backpack while you’re at it?). And once you settle on a pair, remember to break them in before their maiden hiking voyage. Those stylish hiking boots will be nothing but instruments of extreme torture if you neglect the breaking in and end up with feet full of blisters. Ouch.

Best Fashionable Hiking Boots

Okay! Now that everyone is up to speed on their hiking boot facts and figures, let’s take a look at some of the snazziest boot options for your fashion-forward feet.

Polar Women’s Quilted Walking Boots

Dimensions: 9 x 2 x 9 inchesPolar Womens Quilted Waterproof Hiking Duck Mid Calf Winter Muck Walking Boots

Specific features: Synthetic upper, rubber sole, a faux-fur lined interior, and lace-up design, fully waterproof, shaft that measures up approximately 13.5 inches from the arch of the foot.

Best use: This boot is suited for wear in cold temperatures, with its high coverage offering mid-calf support. It would perform best on moderately-challenging trails, but isn’t built for heavy-duty load bearing or steep climbs.

The Polar Women’s Quilted Walking Boots offer attractive yet rugged protection against bitter winter weather. The lightweight synthetic construction makes it a more affordable option than pricier boots with leather uppers — not to mention a more animal-friendly choice (the fur-lined interior is faux all the way).

This boot comes in a variety of hues for every hiker, and the rubber sole unit is calendered (formed and pressed directly onto the boot). Five shiny metal eyelets on the front of the boot compliment it’s stylish and adjustable lace-up design. Wearers of this boot cite a roomy toe box and reliable water-resistance among its best features.

While the midsole is not flexible enough to allow for hiking on rough terrain, they are definitely a solid option for a light day hike. This versatile boot is perfect for running errands on a blustery January weekend as well as taking a peaceful stroll through a snowy forest.

Check the price on Amazon

Box Boots for Men/Women Waterproof Leather Duck Boots

Specific features: Unisex boot Box boots Waterproof Leather Duck Boots
for both men and women, boasting a leather upper, warm fleece lining, padded collar, breathable mesh tongue, 1.25-inch heel, and lace-up vamp.

Best use: This boot is well-suited for light trail use, and will perform best on cold, dry days.

Box Waterproof Leather Duck Boots are a solid choice for a basic winter boot. A warm fleece lining will keep your feet toasty in frigid environments, but if you choose this boot, you will want to take a few extra steps to ensure its water resistance.

Despite being marketed as a waterproof boot, user reviews are mixed, with some saying it kept feet warm but not dry. This boot does offer ankle support, but users also reported a lack of substantial cushioning in the midsole. All things considered, this boot seems ideal for the casual winter hiker who avoids slushy days and carries an extremely light pack (or no pack at all).

They might not be able to withstand more than one or two winters of use, but if you’re a weekend warrior who won’t be too demanding on your footwear, this affordable leather option might just be perfect for you.

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Polar Men’s Lace Up Thermal Boots

Dimensions: 9 x 2 x 9 inchesPolar Mens Lace Up Duck Thermal Boots

Specific features: Synthetic upper, calendered rubber sole unit, faux fur lining, 10-inch shaft (from arch), lace-up design, and water-resistant materials throughout.

Best use: This boot is best suited to day hikes on moderately-rough terrain in cold, wet conditions.

Like it’s female-friendly companion, the Polar Men’s Lace Up Thermal Boots provide ample protection against cold, wet winter weather, but not enough flexibility and support for heavy-duty hiking or backpacking. The animal-friendly faux fur lining will keep feet surrounded in warmth for hours, making this boot a great choice for a winter day on the trail.

The lace-up design provides an adjustable fit, and the calendered rubber sole unit provides sufficient traction for somewhat tricky terrain without the burden of a pack. Users report ample wiggle room for toes that stay perfectly toasty.

This boot is available in a variety of colorful shades guaranteed to make you a sharp dressed man in the wilderness as well as when you’re braving a blustery blizzard in the stands of a playoff football game.

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MIA Women’s Maylynn Winter Boot

Dimensions: 4 x 3 x 2 inchesMIA Women's Maylynn Winter Boot

Specific features: Synthetic upper and sole, lace-up vamp, padded collar, a warm faux shearling lining, lugged tread, a 7-inch shaft from the arch of the foot, and a 1.75 inch heel.

Best use: Solid choice for traversing city streets on cold, damp winter days, but their moderate tread makes them better fit for sidewalks than rough terrain or adventurous trails.

One of the most fashion-forward boots available, the MIA Women’s Maylynn Winter Boot shouldn’t be your first choice for rugged, off trail hikes, but they’re more than capable when it comes to keeping feet warm and cozy while out and about in winter.

The Maylynn is entirely synthetic from upper to interior to lugged sole, which makes it lightweight and affordable, but not water-resistant or particularly hardy when it comes to abrasions from rough terrain. The faux shearling lining and sweater trim are effective at retaining heat and keeping the winter chill at bay while adding to the boot’s overall visual appeal.

Users report that the lightly cushioned footbed is comfortable, but not made for absorbing significant amounts of shock or helping you bear the load of a heavy pack. This boot will serve you well on a light hike on a dry winter’s day (and will definitely keep you looking cute on urban treks), but it is far more fashion than function.

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Timberland 6″ Premium WaterProof Boot

Dimensions: 11 x 4 x 7 inchesTimberland Men's 6 Premium Waterproof Boot

Specific features: Premium leather upper, seam-sealed waterproof construction, 400 g of PrimaLoft insulation, a padded collar for comfortable ankle support, 100% recycled boot laces, rustproof hardware, and a durable rubber lug outsole.

Best use: Versatile workhorse of a boot that will serve the wearer equally well while stomping through puddles on rough trail terrain or at a busy worksite in the driving rain.

Timberland’s original waterproof boot was designed over 40 years ago and continues to be a bestselling favorite among outdoor aficionados and workers alike. These boots feature unique anti-fatigue cone support technology to provide you with long-lasting comfort during long, multi-day hikes, and the rubber lug outsole can handle an uneven trail with ease.

Timberland’s PrimaLoft Eco insulation is made from 50% recycled synthetic fibers that are compression-resistant and maintain warmth even when damp. The leather used in this boot is imbued with special waterproof properties during the tanning process, and extra insurance against moisture is provided with either seam-sealing or an internal waterproof membrane.

As the Timberland 6” Premium Waterproof Boots have an upper crafted from 100% high quality leather, you should expect to spend a fair amount of time breaking them in for optimal comfort and fit. These boots cost extra than some other varieties featured here, but this time-tested boot is worth every penny.

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DailyShoes Women’s Comfort Boots

Specific features: Synthetic materials, DailyShoes Women's Comfort Round Toe Mid Calf Hiking Outdoor Ankle High Eskimo Winter Fur Snow Boots
high-traction rubber sole, faux fur trim, a 12.5-inch shaft height from the arch, and quilted sides.

Best use: These boots can tackle deep snow with ease, and their deep lugs make them a good choice for wet winter hikes on uneven terrain.

Animal lovers will adore the vegan faux leather of these entirely synthetic boots, and the fluffy faux fur trim around the 12.5 boot opening provides more critter-friendly comfort. The water-resistant cloth keeps your feet dry in deep snow, and the mid-calf shaft height provides ample ankle support.

These boots are equally appropriate with a sweater dress and leggings as they are with your favorite hiking outfit, and users report that the DailyShoes Women’s Comfort Boots are rugged enough to last through several winters.

The lace-up vamps enable each wearer to adjust the snugness of fit, and users day they are a good option for those with wider calves. Faux fur insoles make each step feel like walking on a silky bearskin rug — with the peace of mind that comes with knowing that no bears were hurt in the making of these chic kicks.

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Final Thoughts

There are clearly just as many stylish hiking boot options as there are snowflakes in winter — with each option being just as unique from the next. When you’re in the market for a set of capable-yet-cute hiking boots, you can’t go wrong if you know just what to look for when it comes to your personal activity level and aesthetic demands.

Fashionable boots

Do you have a favorite pair of hiking boots that manage to marry pleasing design with dogged durability? Or have you worn any of the brands featured here? Let us know all about it in the comments!

Russell McCarty
Russell McCarty

Russell considers backpacking one of his great passions in life. He actually managed to transform his passion into a living becoming a professional adventurer. Russell loves long-distance backpacking and he enriched his portfolio with famous trails like the Alaska-Yukon Expedition or the Appalachian Trail. With thousands of miles under his feet, Russell is the expert to consult when it comes to how to prepare for a successful outdoor adventure.

  • Lisa Hogenson

    I was a little afraid that stylish hiking boots wouldn’t be functional hiking boots, but I bought the Polar Women’s Quilted Walking Boots mentioned above and I’ve been happy with them. They look good, they’re comfortable, and they keep my feet pretty warm (if it’s below 20 degrees, I use a toe warmer.) Good value for the money!

  • Russell McCarty

    This is my sister’s favorite and I don’t blame her. It’s a good hiking boots and it looks fab. I can say one things, these boots are pretty neat and you’re going to have a great experience with it.

  • Holly Edwards

    My Dailyshoes Women’s Comfort Boots are so cute! They’re super warm, comfortable and I have even worn them when I was driving with no problem. Just spray them with a water repellent and you will be good to go!

  • Russell McCarty

    Those are really cute boots – I agree!
    Make sure to check out some crowd favorites such as the Polar Women’s Quilted Walking Boots and the Box Boots for Men/Women Waterproof Leather Duck Boots, among others.
    Thanks for dropping by Holly!