Timberland US

How to wear hiking boots?

Before you hit the ground running on your next adventure, you need the best hiking boots out there. But, how do you know what to wear with your new pair of boots on any given day? The average temperatures in the United States can fluctuate rapidly by state

If you’re hiking the Pacific Crest Trail in California, you’ll need to dress for warm and temperate weather with plenty of rainfall. Trekking Acadia National Park? You’ll need to bring a thick pair of socks and a couple of extra layers when the weather cools down right off the bat.

Can I wear hiking boots everyday? Curious about how to wear hiking boots in men’s fashion? Whether you’re heading out for a day hike, backpacking, or are planning to travel long distances, how you style hiking boots is key. Let’s explore what to wear with a pair of your favorite Timberlands’ before you hit the trail.


The best way to style hiking shoes is to dress for the climate and activities you have planned. For everyday wear, pair your stylish hiking boots with skinny jeans and a laid-back plaid shirt. For a more intense day on the trail with hikers, wear shorts and a pair of waterproof hiking boots to avoid blisters.

Timberland Original Yellow Boots are a timeless addition to any collection. We built the original Timberland® waterproof "yellow" boots in 1973, but it's really those who've pulled them on year after year who’ve made them the iconic shoes they are today.


The best way to wear hiking boots, trail runners, backpacking boots, and hiking footwear is with skinny jeans because the boots fit right over the top of the boot. Round out the outfit with a bomber jacket or a leather jacket before you head out the door. 

Avoid boot-cut jeans or other less form-fitting denim alternatives. If you prefer an option with more freedom of movement, consider wide-leg trousers or boyfriend jeans that are cut off at the ankle for a more breathable fit. If a tall cut doesn’t fit well, simply roll the pants at the hem for a more casual ensemble.


Leggings are a versatile option to wear with hiking boots because they tuck seamlessly into the ankle of the boot. A pair of hiking boots with leggings can transition your wardrobe from spring to fall and even carry you through the winter months. 

As temperatures drop, a solid pair of SmartWool socks, hiking socks, insoles, and a padded leather collar offers a comfortable fit around the ankle. Plus, premium leather uppers in our classic Tan color work well with any pair of leggings.


Yes,  you definitely can wear hiking boots every day. All Timberland boots offer optimal support and premium leather uppers for lasting durability. As with any shoes, it will also take less time to break in hiking boots if you wear them often as you hike the backcountry on your next backpacking trip in cold weather.

The Men’s and Women’s Timberland Premium 6-Inch Waterproof Boots are specifically engineered with a direct-attach construction for optimal cushioning and durability. Plus, top-quality leather lining and rustproof hardware guarantee your shoes will last a lifetime. If you plan to tackle a cross-country hike, take advantage of an anti-fatigue Vibram sole, toe box, strong midsole, gore-tex construction, and superior ankle support, and a removable footbed for all-day comfort on long hikes.


Yes. Hiking boots have long been a style staple for any season. They strike the perfect balance between fun and functional and work for all seasons when styled well. The pursuit of chic yet comfortable everyday style is a universal goal, and that’s where Timberland comes in with our hiking gear. 

From a 2 mile hike to mountaineering, celebrities have worn Timberland boots in serious style. Take a page out of Pharrell William's book and design your own Timberland boots in a signature happy color. Then, pair them with a waterproofing bomber jacket and a sought-after pair of Chinos.

If the classic Original Yellow Boots are more your thing, take a tip from top model Karlie Kloss and keep it classic. Pair high-rise jeans in light denim with a crisp white tee for a timeless, laid-back look.


Yes. Shorts are a great alternative to long pants or leggings, especially when hiking in warm weather. While shorts and boots might seem like an odd combination, you can easily pull off this practical look with the right accessories. 

Wearing shorts with hiking boots have a range of benefits, especially if you’re always on the move. Hiking in the hot sun can be stifling, and shorts allow for optimal breathability. Plus, you don’t need to worry about your jeans or pants being too long or cuffing them at the ankle. 

The secret to wearing hiking boots with shoes involves carefully curating your look for day hiking. Pick ankle or crew-length socks for added comfort, and consider the width and length of your shorts. Pick shorts that taper on the edge and fall above the knee. 

Keep an eye out for key features including the type of terrain you're walking, the relevant weather conditions, as well as the length of your hike. Shop Timberland Boots today and tackle your next adventure in style.