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A guide to finding comfortable boots

2024-04-11

A guide to finding comfortable boots

Model standing on orange block in Timberland boots

From the trailhead to your own backyard, comfortable ankle boots are a must for any adventure. As the gear that keeps you moving forward, the right footwear can make or break your experience on the trail.

When it comes to finding the most comfortable hiking boots, pay close attention to fit, style, and overall size. Plus, keep an eye out for key features including a waterproof membrane and durable rubber outsole with a lacing system to help you get a grip on uneven terrain.

Timberland boot sole

Let’s explore how to find the most comfortable hiking or mountain boots for you this season in a few simple steps.

How do I choose hiking boots?

Before you tackle the trail, pick a pair of boots with the right fit, function, and components for the type of hiking you’re tackling. For instance, boots for day hikes tend to have a mid to high-cut that requires little break-in time, while backpacking boots have a high cut and are designed for heavier loads.

With that in mind, what are the most comfortable boots for men? What about the best walking boots for women? Here are a few key things to keep in mind when choosing the right footwear for you:

First, choose the right type of shoe

From day hikes to mountaineering adventures, there are endless styles of boots for different needs. For instance, hiking shoes have flexible midsoles and are ideal for ultralight backpackers on short trips. Day hiking boots also flex very easily, but may not offer as much support for expert backpacking in harsher environments.

If you’re planning on a morning jog through the woods, standard running shoes might be your best bet. Consider the length of your trip and the nature of the terrain you're trekking and go from there.

Pick the right size

Size is perhaps the most important element to consider when finding comfortable boots. Generally, hiking boots should fit snugly around the foot with just enough room to easily flex your toes. If your big toe touches the front toe cap while you’re standing up straight, definitely size up.

If you’re ever in doubt, you can easily measure your foot length at home with a measuring tape. Use our Timberland Sizing Guide for reference.

Try them on with socks

Pay close attention to the thickness of the socks you’re likely to wear out the door. Boots that seem to fit well with thin socks will instantly be too tight if you opt for thicker, wool alternatives. Remember to always opt for a pair of quick-drying boot socks in a polyester blend for added comfort.

Test fit at the end of the day

Your feet can swell up to a half size larger than normal over the course of a long day. Consider trying on your Timberland 6 inch Premium Yellow boots towards the end of the day to avoid picking a pair that’s a bit too tight for you.

Be sure to break in your boots

As excited as you may be to test out your new favourite Timberlands, be sure to wear your boots in the house or for a short trip to the shops before embarking on a long hiking trip. This will wear in the leather upper and help the boot conform to your fit for optimal ankle support. Read more about stretching and softening leather boots.

Invest in EVA midsoles for added comfort

Go for midsoles or footbeds to guarantee comfort and support on all-day adventures. While EVA is currently the most widely used midsole for shoes globally, a range of midsoles is available for hiking boots.

What are the most comfortable women’s hiking boots?

The most comfortable walking boots for women are lightweight, waterproof, and offer extra support while keeping your feet dry in any weather. The best walking boots for women are made of high-quality leather and engineered with modern footwear technology for long-lasting protection.

What are the most comfortable ladies walking boots? Whether you’re looking for women’s walking shoes or a solid pair of women’s waterproof hiking boots, here are the best hiking boots out there:

  • Best Waterproof Boot: The Chocorua Gore-tex® Hiker For Women In Brown is our top-rated women’s hiking boot, and it’s easy to see why. Equipped with a durable rubber lug outsole designed for optimum traction, these boots guarantee your feet stay dry with breathable, waterproof GORE-TEX™ technology. With functional features like rustproof hardware and a durable rubber outsole, these boots only get better with age.

  • Best Anti-Fatigue Boots: The Mount Maddsen Gore-tex® Hiker For Women In Brown offers a removable anti-fatigue footbed so you never slow down on the trail. Plus, a compression-moulded EVA midsole and custom rubber lug outsole ensure you’ve got a strong grip both inside and out.

  • Best Low-Top Hiker: If you prefer a bit more flexibility around the ankle, then the Greeley Gore-tex® Low Hiker For Women In Grey is the ultimate pair for you. Made exclusively from Better-Leather suede, these shoes are sustainable and stylish. Plus, a lightweight OrthoLite® footbed and EVA-blend cushioning offer ample cushioning minus the bulk. Similar to the Salomon x Ultra Collection or La Sportiva hiking shoes, these low-top hikers are ideal for more technical hiking adventures.

Female model in beige Timberland boots

What are the most comfortable boots for men?

The most comfortable hiking boots for men offer all-day comfort and long-lasting protection in any climate condition. From waterproof hiking boots to walking boots, all-terrain footwear made of nubuck or leather are the best option.

Here at Timberland, we take pride in building footwear with comfort and rugged good looks to boot. A seamless Goodyear Welted Construction™ and customised Vibram® outsoles give your shoes a longer life as you take it all in stride.

  • Best Mid-Hiker For Men: If you’re looking to level up your look without sacrificing function, go for the Euro Sprint Mid Hiker For Men In Yellow/Black. A durable rubber lug outsole offers superior grip while sustainable leather and brass hardware add an industrial touch.

Male model in brown Timberland boots

Should I buy walking boots a size bigger?

Yes, many people actually prefer walking boots to be a half size or even a full size bigger than their standard shoe size. Sizing up offers ample room to accommodate thick hiking socks or unexpected foot swelling after a long day on the trail.

Plus, your feet tend to slide within the shoe when you’re hiking downhill. If your toes already touch the toe cap, the natural shift of your feet due to gravity may be uncomfortable. At Timberland, all of our footwear is engineered to American size standards, but you can easily take a look at our convenient Adult Footwear Size Chart to convert to your international size.

The next time you buy hiking boots, consider standing at an angle on an inclined plane to mimic uneven terrain on the trail. Then, jump a few times to allow your feet to shift. If your toes immediately hit the top of the boot, go up a half size or even a full size just in case.

If you’re buying for a loved one and not quite sure of their preferred size, give them the gift of choice with a Timberland digital gift card.

Which walking boots are best for wide feet?

If you have wide feet, the best walking or hiking boots for you are medium-width that is constructed with a wide last, which is the mould around which the shoe is formed. While some brands use narrower lasts, Timberland tends to run wide to accommodate all explorers.

Here are a few of the best walking boots for wide feet:

  • Best wide-fit lightweight boot: If you’re looking for an all-leather waterproof hiker that won’t weigh you down, we’ve got you covered. The Timberland White Ledge Hiking Boots offer a wide fit with a seam-sealed waterproof construction with a shock-absorbing midsole and outsole for added traction on rough surfaces.

  • Best wide-fit waterproof boot: The Chocorua Gore-tex® Hiker For Women In Brown is an all-leather hiking boot with our proprietary Timberdry inner layer. Available in both regular and wide widths, this boot offers two unique yet durable layers of moisture protection.

When it comes to how to choose walking boots, you can't go wrong with a pair of our classic, timeless Timberland 6-inch Premium hiking boots that are stylish, iconic, and built to last a lifetime. From comfort to durability, all of our boots are built to go the distance so that you can, too.