Vintage Hiking Boots for Men and Women

Picture reaching that incredible lookout point on your favorite trail and putting your feet up to admire the view. Now take that Instagram perfect pic, while catching your stylish vintage boots in the shot.

This is no place for dull and ordinary shoes. Yes, hiking gear should be practical, but this doesn’t mean you need to sacrifice how you look. Why not embrace nature in old fashioned style.

Vintage hiking boots are the perfect marriage between retro style and functional footwear. Walk them hard or simply enjoy them for their classic, retro design. If you plan to explore the endless trails of your closest National Park, or simply take in the view from a boat on a lake, do it old school!

We have hand picked the best selection for men and women. Not only do they look fantastic with their tough brown leather, unmistakable metal eyelets and red laces, they are tried and tested footwear that will get you where you are going in style.

Reese Witherspoon Boots from the Movie Wild

Danner Hiking Boots, originally designed in the early 1970’s, came into the spotlight once again when Reese Witherspoon wore them in the movie “Wild”.

You may not be taking on the Pacific Crest Trail, but this timeless ladies design, with its red laces and metal eyelets shout classic outdoor style. They are an essential addition to any outdoor wardrobe. The leather has an antique look that wears beautifully over time, adding to their authentic vintage feel.

These US made, leather vintage hiking boots have a rubber sole and stitchdown construction, which means that it’s stitching goes through the upper and outsole for increased strength and stability. They also offer excellent arch support and have a Dri-Lex lining that provides increased breathability and comfort. They are ideal for both host and cold weather conditions.

If you are looking for a quality shoe for getting into nature without sacrificing on style, this classic style is a must and only look better are they get older.

Timberland Brown Waterproof Boot

The vintage inspiration behind the styling of these men’s Timberlands in unmistakable. The brown leather, red laces and D-ring lace ups finish off the look perfectly.

We love the additional detail in the stitching, the two tones sole and the wool lining at the collar of the boot. The Timberlands also has a Gore-Tex breathable, waterproof membrane.

The leather will show scuff marks, but this is a characteristic of the leather and with a light rub, marks can be removed.

These tough treaded Timberlands have that hipster style along with all the functional performance of a quality hiking shoe.

Kodiak Old School Hiking Boots with Red Laces

Like the Timberland men’s hiking boots, the Kodiak old school ladies design have a waterproof membrane and sealed seams. The rubber sole has a chevron design for improved grip on slippery surfaces.

For the classic old school look, the red lace and eyelets on the brown leather are our first pick, but if you are looking for something slightly different, this heeled hiking boot also comes in black, caramel and olive. The gray, padded detail at the back of the shoe is an attractive additional detail.

These are great go-to shoes if you like a style with a heel that can handle both cold and wet conditions.

Woolrich Men’s Retro Look

The Woolrich Mens winter boot is wool lined making them a warm and cozy winter hiking boot. Like the Timberland, it is also waterproof.

As with the other designs, this retro look has a leather outer, D-ring lace up and rubber sole with a deep tread for good grip. It has a thin tongue to avoid bulk on the arch of your foot and a wool lining at the cuff to avoid chafing.

It comes in 3 design finishes; a full grain ginger with tweed lining, full grain vintage black and the tin pan which has the traditional retro red laces.

It has a slightly stacked heel and felt-flex module that adds extra warmth and cushioning to the footbed.

It is a great traditional hiking boot, but it’s fashionable details and comfort also make it the perfect winter shoe for everyday wear.

Woolrich Women’s Vintage Style for Hiking

The Woolrich Women’s Rockies winter boot has that traditional vintage feel with an added wool fabric finish on the heel, this sets it apart from the other full leather looks in our selection.

It has a synthetic sole and a slightly raised heel. The outside of the shoe is water and stain resistant. The shoe inner is lined with Woolrich wool and has a felt flex midsole for added warmth and comfort.

You can choose from 3 finishes; Vintage black, Stucco/Blanket Red Wool which both come with red laces and Quill/Camo Wool with white laces.

These fashionable shoes are more about style than roughing it making them a good match for easy to moderate hikes or alternatively, completing that natural outdoor girl look when the occasion calls for it.

Wolverine Classic Leather Raider

One look at these rugged leather Wolverine’s for men will tell you they are tough! The double and triple stitching on the panels and the solid sole makes them look indestructible. They may not have the retro red laces (a detail that can be changed), but they are built to withstand the toughest of conditions and have a slip-resistant rubber sole for wet weather.

Designed primarily as a work footwear, the shoe it does not compromise on comfort and flexibility. The excellent cushioning and foot support make them comfortable to wear for long hikes or hours on the job.

This shoe design accommodates wider feet, but if you have a narrower foot, a thick pair of socks and lace adjustment will have them perfectly snug on your feet.

Wolverine is an established American brand that pride themselves on superior materials and craftsmanship. If you are looking for a super tough and comfortable footwear for outdoor adventuring or a harsh work environment, these are the guys for the job.

Dr. Martens for Ladies

The Dr. Marten’s say glamping more than camping, simply, they look great, but we’d keep these pretty girls off the hiking trail. The suede leather finish, brass lace-ups and faux fur trim are more cute than tough, but the leather finish and semi transparent sole still maintain that old school vibe.

Dr. Martens have a reputation for quality products and this stylish design is no exception. The heel is higher that any other in our range, this makes them less ideal for hiking. But if you’re looking for a little extra height and fashion from a boot, they’re perfect.

They are fully lined and perfect, warm, winter boots. They’re the ideal accessory to finish of that outdoor-girl look.

How to Choose Classic Outdoor Footwear

To get that “vintage” look, you’ll probably need to go for brown leather, red laces and copper/steel eyelets. But these are merely guidelines. Let your heart decide what’s vintage and what isn’t.

First, know your size. (The reviews on the supplier’s website will let you know if they run smaller or larger.)
Ankle support. The higher the boot rises above the ankle, the more support it will provide. If you want a wider range of movement, choose a shorter ankle support or lace the shoe to a comfortable height.
Choose a snug fit. Hiking footwear should never be tight, but should fit comfortably, allowing your toes room to move.
Test them out with the socks you plan to wear. You may have to select a half size up to compensate for thicker winter socks.
Leather should be “broken-in” on shorter hikes so they have time to soften and mold to the shape of your foot.

One of the biggest benefits of wearing boots over shoes, is the ankle support. If you plan to carry a heavier pack, or walk uneven ground, the additional ankle support makes these tasks so much easier.

The natural durability of leather is ideal for use on almost all terrain and are a great addition to complete any stylish wardrobe.

Getting out into nature is about that serene feeling of soaking up your environment and becoming one with your surroundings. When you capture that perfect Instagram moment, you may as well look the part.