10 Best Cute Hiking Shoes and Boots to Take You From Trail to Town

We love the stylish Timberland Mt. Maddsen Mid Waterproof Hiking Boots' fantastic comfort and grip.

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Travel + Leisure / Sabrina Jiang

Perfect hiking shoes can hack it on the trails just as much as going downtown for dinner and drinks. Finding that ideal balance of functionality and style isn’t always the easiest task, though. With so many options to choose from, it can be overwhelming to land on the right hiking shoes or boots for you that offer versatile usage and durability. It’s key to evaluate your needs first, and once you have a solid foundation of the type of terrain and conditions you expect your hiking shoes to handle, then you can narrow down the fashion aspect. 

To help with your search, we researched dozens of options to find the best hiking shoes and boots on the market that’ll be ready for anything your day throws at you while keeping you feeling cute and stylish, to boot. Our favorite overall, the Timberland Mt. Maddsen Mid Waterproof Hiking Boots, are equal parts stylish and sustainable and can handle almost all weather conditions. Whether you’re summiting a mountain before shopping with friends or going on a picnic date at the lake, these hikers will have you covered.

Go seamlessly from trail to town in these 10 best cute hiking shoes and boots:

Best Overall

Timberland Women's Mt. Maddsen Mid Waterproof Hiking Boots

Timberland Mt. Maddsen Mid Waterproof Hiking Boots


Why We Love It
  • They can handle almost every kind of weather.

What to Consider
  • They run a little narrow, making them less suited for wide feet.

We love the versatility of the Timberland Mt. Maddsen Mid Waterproof Hiking Boots, and the fact that they’re ruggedly cute doesn’t hurt either. Their waterproof design, gusseted tongues, and footbed cushioning mean they can tackle and withstand the elements with ease without being too clunky to wear out to lunch after your morning hike. They offer great traction for the tricky spots on the trail so you can feel confident even when things get slippery. Crafted eco-consciously, this pair of boots is made partially with recycled materials, like PET polyester.

Your feet will stay dry and plenty warm as you navigate trails to a summit, around a lake, or anywhere else that you might get caught in a surprise rainstorm. Post-hike, there’s no need to change your shoes as you celebrate with a brew at a local spot or even dinner, as these shoes can be dressed up or down (as much as any hiking shoes can). 

Price at time of publish: $90

The Details: 6-11 (with half sizes) | 2.4 pounds per pair

Best Suede

Sorel Out N About III Conquest Boot

Sorel Out N About III Conquest Boot


Why We Love It
  • They come in a handful of cute color combinations.

What to Consider
  • They run a bit small; consider sizing up half a size.

Sorel has outdone themselves with these hiking inspired winter boots; they’re jam packed with all the features we crave in cold weather pursuits, and yet they manage to maintain a sleek design. These low profile bootie-style hikers will keep your feet toasty warm with the microfleece lining as you romp around the city or venture along the trails. Although they’re not quite suited for technical hikes, these Sorel boots can hack it on easy to moderate trails as well as errands and everything else you need to do around town. Wet surfaces won’t be an issue due to the vulcanized herringbone outsole that’ll help grip and provide traction, and your feet will stay dry from the snow with the waterproof suede. The platform sole design provides extra cushioning so you can wear these all day long with no problem, too. 

Price at time of publish: $145

The Details: 5-12 (with half sizes) | 1.73 pounds per pair

Best Retro Design

Teva Ridgeview Mid Hiking Boots

Teva Ridgeview Mid Hiking Boots


Why We Love It
  • They’re well-equipped to handle wet weather conditions and offer great ankle support.

What to Consider
  • The lacing system takes a little more adjustment than other boots.

We really love the retro color-blocked upper portion of the Teva Ridgeview Mid Hiking Boots. They’re the perfect blend of vintage aesthetic and modern design that excel in harsher weather conditions with solid waterproofing and stabilization. They perform well in anything from sun to rain and in mud or snow. The slightly springy footbeds give you that extra pep in your step for venturing along a hiking trail or skipping across the city to refuel with pizza. Traction is one of the highlights of these boots as well, with the Vibram Megagrip outsoles gripping almost any type of terrain, from street to summit. The classic Teva Ridgeview throwback design has never really gone out of style…and these are proof.

Price at time of publish: $160

The Details: 5-11 (with half sizes) | 1.5 pounds per pair

Most Breathable

Danner Trail 2650 Hiking Shoes - Women's

Danner Trail 2650 Hiking Shoes - Women's


Why We Love It
  • They’re impressively lightweight and breathable.

What to Consider
  • They tend to run half a size small.

The Danner Trail 2650 Hiking Shoes are ready for your day’s adventures straight out of the box—and for that, we are thankful. They’re a comfortable fit for almost all types of feet, whether narrow, average, or wide, and have the streamlined design of a sneaker. With their superior durability and functionality, it’s no surprise that they nailed the breathability factor, too. Mesh liners help keep air flowing to keep moisture at bay and aid in their quick-drying ability. The Megagrip technology on the shoe’s outsoles performs well in wet and dry terrain, and the low profile of these hikers will keep you nimble on your feet, while the reinforced heels offer extra support when you need it most. Whether you’re walking the dog, going on a weekend hike with friends, or grabbing brunch, these cute and breathable hiking shoes fit the bill. The Danner Trail 2650’s are a do-it-all type of shoe and an unbeatable choice that looks good while enjoying your favorite activities. 

Price at time of publish: $142

The Details: 5-11 (with half sizes) | 1.1 pounds per pair

Best Boot/Sneaker Hybrid

Forsake Patch Hiking Boot - Women's

Forsake Patch Hiking Boot - Women's


Why We Love It
  • They’re comfortable all day long.

What to Consider
  • They run slightly small, with a narrow toe box.

Can’t decide between a boot or a sneaker? Don’t. The Forsake Patch Hiking Boot has combined the best of both worlds in these shoes with the cushioning of a sneaker and the support of a hiker. This “sneakerboot” has waterproof leather and a gusseted tongue so wet trail conditions or unseemly weather aren’t an issue. You don’t have to worry about traction either: The lugged outsoles will grip most types of terrain, giving you the confidence of both functionality and style. Although these boots aren’t recommended for more technical or lengthy hikes, they’ll do the trick for casual walks, day hikes, and everything in between. We love the color combination choices offered too, which appeals to a wide range of styles, from charcoal and blue to a classic brown and navy pairing. 

Price at time of publish: $120

The Details: 6-11 (with half sizes) | 1.9 pounds per pair

Best Budget

Columbia Women’s Newton Ridge Plus Hiking Boot



Why We Love It
  • They break in quickly.

What to Consider
  • Though they’re ideal for beginners, most experienced hikers might need something with more support.

The Columbia Newton Ridge boots are a classic design that really never gets old, because they both look great and get the job done. We love how quickly they break in and that they can handle more than basic nature walks as well as casual days hanging around town. These hikers are waterproof and won’t have you running inside on a rainy day or hesitating at a quick rock-hopping stream crossing. As a bonus, they come in a wide array of sizing, including half and wide, making them ideal for most foot types. The red laces and brown leather are a fashionable look that goes with almost anything, so this an easy choice for a budget hiking shoe that can also be worn with jeans at dinner.

Price at time of publish: $74

The Details: 5-12 (with half and wide sizes) | 1.75 pounds per pair

Best for Trail Running

Altra Lone Peak 6 Trail Running Shoe

Why We Love It
  • They offer extra grippy traction.

What to Consider
  • If you’re in between sizes, size up by half a size.

The cutest trail runners you ever did see, the Altra Lone Peak 6 Trail-running Shoes come in a variety of colors and make sure you stay protected from rocky terrain while running. Feel sure-footed as you navigate the trails with the updated StoneGuard from the previous model, as well as a built-in rock plate for added protection. The toe box aims to keep your toes comfortably spread out, and the midsoles and contoured footbed offer cushioning and support without going overboard and feeling clunky. Caught in the rain or another wet situation? Don’t worry—the quick-dry Air Mesh uppers are specifically designed to let water out fast if you need to cross a stream, accidentally step in a mud puddle, or get caught in a serious rain storm. Traction is on point as well, with MaxTrac outsoles featuring multi-directional lugs. For trail runners looking to stay dry and stylish without sacrificing on comfort, the Altra Lone Peak 6 are a great choice.

Price at time of publish: $140

The Details: 6-12 (with half and wide sizes) | 1.08 pounds per pair

Best Wide-toe

Merrell Antora 2 Wide Hiking Shoe

Merrell Antora 2 Wide Hiking Shoe - Women's


Why We Love It
  • You can use them for trail running, hiking, or dinner in town.

What to Consider
  • They have moderate cushioning, which isn’t ideal for more technical hiking or running trails.

We love the grip and support incorporated into the design of the Merrell Antora 2 Wide Hiking Shoe. Not only that, but the wider toe box is perfect for those in need of a roomier shoe and offers a smooth feel as you hike. If that wasn’t enough, the rainbow color is the vibrant and cute look that is all too rare in an outdoor shoe. The built-in rock plate helps distribute the shock absorption as you navigate the trails and keeps your feet from feeling most rocks. The 4-millimeter lugs offer great traction, so whether you encounter wet, dry, or muddy conditions, you can feel confident. While it’s a little more rigid than other trail runners, this stylish pair will get the job done and have you feeling cute all the way through your morning hike to afternoon drinks with its mood-boosting color scheme.

Price at time of publish: $120

The Details: 5-11 (with half and wide sizes) | 1.25 pounds per pair

Best Lightweight

Jag Distressed Hiking Boot

Danner Jag


Why We Love It
  • It’s an 80’s classic tied into a hiking shoe.

What to Consider
  • They run a little narrow.

An homage to the 80’s design, the Danner’s Women’s Jag boot was brought back into their line-up better than ever. With a combination of suede and leather as well as a waterproof barrier, these hiking shoes are the complete package. The low-profile was designed for “everyday wear,” making it ideal for anything from a jaunt to the viewpoint to a weekend backpacking trip or catching up with friends at a brewery. Since they’re incredibly lightweight, they won't weigh you down when you need to pack light. The OrthoLite Footbed is welcome cushioning but also removable, so you can take it out completely or substitute your own for a more tailored support. The fact that it comes with an extra pair of laces is an added bonus and gives it major style points. For those who enjoy 80’s era fashion in their hiking footwear, look no further than the Danner Jag.

Price at time of publish: $190

The Details: 5.5-10 (with half sizes) | 29 ounces per pair

Best Leather

Keen Pyrenees Hiking Boot - Women's

KEEN Pyrenees Hiking Boot - Women's


Why We Love It
  • These boots are great for more involved hiking trails.

What to Consider
  • They’re a little heavier than some of the other comparable options.

With pink laces and beautiful leather design, the Keen Pyrenees Hiking Boots are equipped to handle serious hiking trails while maintaining a stylish appearance. The traditional all-leather material is waterproof and will keep your feet dry and warm, no matter what adventure you take them on. They’ll slip on and off with little trouble due to the rear pull tab, and you can hike with confidence knowing the multi-directional lugs have your back in any type of terrain where you need grip. The toe box is roomy enough for those with wider feet, and breathable membrane will keep moisture at bay so your feet remain comfortably dry in addition to being as odor-free as possible when hiking. Although these can tackle more intense hikes, they’re still cute and stylish with jeans or leggings and go from trail to town with ease. 

Price at time of publish: $108

The Details: Sizes: 6-11 (with half sizes) | 2.2 pounds per pair

Tips for Buying Trail to Town Shoes and Boots

Prioritize traction

When shopping for shoes that can handle the hiking trails as much as your adventures around town, it’s ultimately key to prioritize traction. Finding a pair of shoes or boots with good grip can make all the difference, whether you’re venturing to a scenic peak or navigating wet streets. There are plenty of options that offer solid traction with multi-directional lugs so you feel confident in your moves along the trail or through town, no matter what the weather conditions. Make this a priority along with style, and you’ll find the best combination of trail-to-town shoes that fit your needs.

Consider wardrobe versatility

Thinking about the main situations you’ll be using your stylish hiking shoes or boots can help narrow down your search, and finding something that can go the distance as far as usage is crucial. Rather than packing different shoes for various situations, it’s best to find a pair that can do well with all your activities. Purchasing shoes that compliment hiking pants or leggings as well as jeans or even a dress or skirt is the ultimate goal for a trail-to-town shoe. 

Frequently Asked Questions
  • Should I wear boots or shoes for hiking?

    It all depends. The decision to wear hiking boots versus shoes is really a personal preference, but also relies on experience, features of the footwear, difficulty of the trail, and conditions you’ll be exploring. Beginner hikers that stick mostly to less technical trails and casual outdoor activities should feel confident exploring in lighter weight hiking shoes or trail runners as long as they offer some grip, support, and water resistance. The more lengthy or technical the trail, the more you may want to veer towards a heftier boot that will give you extra cushioning and stability, as well as waterproofing and superior traction for varied terrain so you don’t feel pesky rocks as you move along the trails.

  • How should hiking shoes fit?

    Hiking shoes should fit snugly without feeling too cramped or tight. You don’t want them slipping off your heel as you wander around, as that will cause blisters, but you also need to allow your toes a bit of room to move—it’s a delicate balance. Keep in mind that your feet may swell naturally throughout the day, especially with physical activity, and the thickness of the socks you plan to wear with your hiking shoes or boots will affect fit. When you try your prospective shoes on, spend some time walking around in them, lace them up properly, and take note of any hotspots that seem to rub or poke your foot in an uncomfortable way. Although some boots or shoes may need time to break in, you’ll get a solid feel for if there might be problem areas of discomfort. If you’re able to visit a store where you can get your foot measured professionally, that’s your best bet for the most honed in fit. 

Why Trust Travel + Leisure

A hiking enthusiast and travel writer, Lauren Breedlove used her personal experience with finding the right hiking boots and shoes as well as using them on a variety of trails all over the world to write this article. She also scoured the internet, researching and selecting the best women's stylish hiking footwear that can easily go from trail to town. With all these factors, she curated this list of cute hiking shoes and boots for women.

Related: The Best Winter Hiking Boots for Women and Men

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