The Best Hipster Boots

Boots are a staple in hipster fashion. They have to balance that not-trying-too-hard look, but still provide enough style that you get asked on the street, “Hey! Where’d you get those amazing boots?”

Fashion-forward hipsters know that relying on one kind of boot isn’t going to cut it, so here are our top picks for the best hipster boots for your collection. They’re high style, have plenty of conversation-piece details, and give you plenty to humble-brag about when it comes to the story.

The Best Hipster Boots to Keep Your Feet Moving

These boots are durable, long-lasting, and offer plenty of styles. Whether you need that perfect boot for your office-wear or you’re heading into the wild to find yourself, we’ve got a boot to help you get your hustle done.

Let’s take a look.

Grenson Fred Boot – Old English Style

hipster boots

Grenson boots have been handmade in England since 1866. Can you say that about those Walmart boots your frenemy bought on the cheap? Not a chance.

They’re durable, beautiful boots that age gracefully and hold up to a lot of wear and tear.

The Fred Boot comes in this gorgeous brown with details such as alpine grain leather and attractive stitching across the ankle and toe. It’s the perfect brogue style boot with a chunkier bottom designed to handle a little inclement weather.

Leather lining and Goodyear welted rubber soles keep them comfortable and ensure that they last through the years without losing their glorious color.

They age well with fine leather details and are an adjustable lace-up boot. They’re definitely an investment, but you’re paying for a wonderful, small company with handmade details.

Grenson boots are definitely an investment, but they’re a versatile style with lots of class and conversational details everyone is going to notice.

The color is beautiful and ages with a bit of grace with unique details formed around your foot. Unique and timeless at the same time.

Wolverine Evans 1000 Mile Boot – Working Class Hero

hipster boots

Wolverine shoes have a tough reputation, and their boots definitely live up to that name. The Evan 1000 mile boot offers a work boot that’s both durable and stylish with no weird embellishments. Instead, durable stitching and fine grain leather do all the talking.

The leather upper comes from a small batch company, Horween Leather, and the Vibram rubber forepart and heel offers plenty of traction for inclement weather. The construction is a high top lace with a smaller heel, and the waxed cotton laces are an archival pattern.

When even the laces are considered “archival,” you know you’ve got the ultimate hipster work boot.

It’s durable and stylish with all the features you expect from Wolverine and an American made, small-batch boot. It’s durable and a subtle style.

Wolverine comes with a guarantee. Even though it’s a bit of an investment, their work boots offer a clear advantage to cheap work boots along with a singular style that makes Wolverine famous, hipster or not.

This pair can go from your side hustle to your underground show in a heartbeat and protect your feet along the way.

Tricker’s Chelsea Boot – Subtle Luxury

hipster boots

If you’ve got the budget and you want in on an elegant and traditional boot, Tricker’s option is an excellent choice.

Their slip-on Chelsea boot features fine-grain leather in a neutral brown with subtle side details. The sole is a waffle style for easy traction, even in inclement weather.

Tricker’s has a 190-year history of crafting boots with elegant details and rugged features. Tricker’s is credited for designing the first country boot in 1840, ushering in a boot reign that lasts till today. They might be expensive, but they’re definitely going to be one of the most luxurious boots you could bet.

They’re five generations into building the perfect boot, and each one is designed to the exact specifications that make them famous so many years ago.

This dark brown suede will age beautifully and gain the subtle unique details of boots that are well-loved and well worn.

You’re guaranteed a boot that can fit with just about everything you have to wear and will never let you down. And with a simple slip-in design, you can get them off and on quickly for whatever you need.

Tricker's Luxury Fashion Man HENRYCAFFEVLT Brown Suede Ankle Boots | Fall Winter 19
  • ANKLE BOOTS TRICKER'S, SUEDE 100%, color BROWN, Rubber sole, FW19, product code HENRYCAFFEVLT

Clark’s Original Desert Chukka – An Exotic Classic

hipster boots

Clark’s boots take their inspiration from the boots military men wore when in the foreign service. Their simple design is made for work and comfort and harkens back to those desert bazaars in Cairo.

The Chukka is a hipster staple with simple lacing and subtle details. This deep brown leather option offers the chance for unique aging based on your particular foot and gait.

It has a durable sole with good tread and traction and simple leather lacing.

If you want more of a pop, you also have the option of a fun red color that stands out with your outfit. With enough confidence, you could pull off any color.

Each one ages with the same grace as the classic brown leather.

Clark’s has been in business for over 100 years, and you’re the recipient of all that glory. They design both contemporary and classic boots.

They’re a bit more affordable than some of the small-batch boots on our list, but they sacrifice none of the style.

Clarks Men's Desert Chukka Boot, Beeswax, 115 M US
  • Heel Height .94 inches
  • Boot Shaft Height 4.21 inches
  • Boot Shaft Circumference 13.38 inches

Dr. Martens Men’s Church’s Chukka Boot – A 90s Revival Boot

hipster boots

Does your 90s heart sing with joy that the decade is officially back in fashion? Hipsters say it never left, and a classic footwear staple of that decade is the Doc Marten.

These even have a slight wine color to help you fully embrace your 90’s dreams.

It features 100 percent leather for a durable and well-aging material that offers subtle details as you wear them in. The synthetic sole provides plenty of long-lasting wear with lots of traction for inclement weather.

The air-cushioned sole is super comfortable, and the platform is just enough to give you a boost without being an obvious platform. The classic Doc shape gives you plenty of hipster-cred while ensuring your feet are protected.

Dr. Marten always has a versatile style that moves well between work and play. It goes back to the 1960s with that English aesthetic that demands practicality and good value.

For hipsters, this is a great way to get around.

Dr. Martens Men's Church Vintage Smooth Chukka Boot, Oxblood, 7 UK/8 M US
  • 5-eye church monkey boot
  • Air-cushioned, synthetic sole
  • Slip resistant

Ugg’s Butte Men’s Snow Boots – The Ironic Choice

hipster boots

Uggs has a terrible reputation with basic girls and pumpkin spice lattes, but their men’s boots are a well-designed snow boot built for comfort. You can wear them in the ultimate ironic nod to subverting mass fashion for your own self-expression.

They feature waterproof leather and suede upper with a synthetic reinforced toe and heel. It uses a faux fur detail for both warmth and a pop of style.

These offer the perfect ironic conversation piece for confident hipsters. The sole is durable and provides excellent traction for terrible weather so you can get through your commute or your day to day outdoor activities with minimal chance of slipping.

They’re fully seam-sealed and entirely waterproof. Your feet are protected, warm, and full of conversational irony with a side of humor.

UGG Men's Butte Boot, Worchester, 12 M US
  • By UGG
  • UGGpure wool lining
  • Vibram outsole with lug tread. Cuffable shaft

Thorogood Men’s American Heritage Boot – A More Affordable Option

hipster boots

Our final boot is slightly more affordable than some of the luxury options on our list but offers a well made, durable boot in beautiful leather. The style is a throwback with lacing and a simple treaded sole to protect your feet and offer traction.

It has a removable shock absorption footpad with a fiberglass shank. It has a Goodyear storm welt construction bottom and reinforced stitching across the front and sides.

As a bonus for the next time you need party conversation, it can withstand up to 18,000 volts at 60 hertz for one minute with no leakage.

Tobacco oiled leather will age well and uniquely depending on your foot and gait. They’re made in the USA by union workers for those of you with political leanings, and each one offers a durable yet stylish accessory, whether working or in leisure.

Thorogood Men's 814-4200 American Heritage 6" Moc Toe, MAXwear Wedge Non-Safety Toe Boot, Tobacco Oil-Tanned - 9 D US
  • Polyurethane MAXwear Wedge sole
  • Ankle-length work boot with handsome moccasin toe and cushioning wedge sole
  • Slip- and oil-resistant outsole, Tobacco Gladiator Oil-Tanned Leather. Cotton drill vamp lining

Building Your Hipster Boot Collection

Boots are a hipster staple, but to pass the test, they must offer that unique something that you can’t get from the mall. The boots on our list offer durable and stylish details from companies with good stories and long histories of making excellent boots.

Building your boot collection can give your feet protection and ensure that wherever the whim takes you, you’re ready to go. Hiking, commuting, or walking all day to find the best coffee and craft beer, you’re covered with boots from our list, and you’ll get the pleasure of knowing they’ll all wear with unique details made possible by your foot and gait.

Get a good pair of throwback, classic boots with excellent details, and consider your outfit made — every single time.

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