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Men wearing boots

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The Dummies’s Guide to Men's Boots

WTF is a Chukka, anyway?

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You need a pair of boots over the next couple months. It is simply too cold, too wet, too slushy, and even if you live in a warmer climate, too winter to be without a pair. That part is easy. The more difficult question to answer is: What kind?

All that will depend on where you live, what purpose you need your boots to serve, and how much of a child you are (or as I like to say, how much childlike wonder you have). The last part is important only because I require a pair of boots that will prepare me for any puddles or large piles of snow that must be jumped on/around/into. Here are the broad categories of boots to get familiar with before making your decision.

Hiking boots

Hiking Boots

Stylish hiking boots, like Sasquatch, are often spotted in the woods. Stylish hiking boots, unlike Sasquatch, are not folklore; they are real. More designer brands, like Off-White, Visvim, and Rag & Bone, are remaking the hiking boot while heritage labels, like Danner, are trying to keep up with the trend by creating more city-friendly capsule collections — the brand has one not-so-subtly titled “Portland Select.”

The best thing about hiking boots is that no matter how fashion-y they get, they almost always retain some functionality: the gripping sole, the weather-proof material, the indestructibility.

The Hiking Boot’s defining qualities:

  • Typically made out a durable material like leather.
  • It should be waterproof — usually thanks to Gore-Tex “membranes,” an inner layer that work to keep feet dry.
  • Those D-ring eyelets are the best lacing option for a hiking boot. They offer a snug fit that won’t break down.

Work boots

Work Boots

The classic Timberland 6-inch might be the work boot in its purest form. It was created for New Englanders who were described as “honest working people" looking to stay dry and comfortable by the company’s former CEO. The shoe’s functionality and design is inspired by what those people needed out of a shoe.

The Work Boot’s defining qualities:

  • Padded leather collar to prevent your ankles from getting rubbed raw.
  • Rubber lug soles are essential — the chunky grooves on the bottom of the boot provide traction.
  • Almost always made out of leather.

Chelsea boots

Chelsea Boot

The dressier Chelsea boot isn’t recommended if you’re hiking or an honest hard-working New Englander, but if you want to wear the same shoe made famous by The Beatles, the Chelsea is what you’re looking for. Not to be confused with its cousin the Jodphurs (which have an ankle strap) or its more distant cousin the biker (which features a harness around the ankle).

The Chelsea Boot’s defining qualities:

  • Elasticized panels on the ankles.
  • Subtle heels.
  • Pull tabs at the top to help you get in and out of the shoe easily.
  • A more slender and pointed toe.

Desert boot

Chukka/Desert Boot

The desert boot is a type of Chukka boot. They’re the same shape you see above, but the desert exclusively comes with crepe rubber soles because that was the style that 1) British soldiers in WWII wore to avoid sinking into sand, and 2) inspired Clarks to create the desert boot. Chukka’s materials are more up for interpretation.

The Chukka/Desert Boot’s defining qualities:

  • Always either a two- or three-eyehole boot.
  • Ankle-high.
  • The upper (top part of the shoe) is made up of two halves typically from the same leather.

Combat boot

Combat Boot

The use of combat boots dates all the way back to the Roman empire. They are still made for very specific reasons for the actual military — whether that’s stomping through the arctic or extreme heat — and designers make their own versions to give our outfits an edge.

The Combat Boot’s defining qualities:

  • Mid-calf length.
  • Lace-ups without the need to knot the top.
  • Chunky rubber soles to provide traction.

Rain/snow boots

Rain/Snow Boots

The boot you need to tackle all the elements. We’re clumping these two together because they’re multi-purpose and because, well, as my coworkers now know, I am a moron. (Or am I?)

The above is a duck boot. It serves the best of both worlds: It has a sole made out of rubber (the go-to rainboot material on the bottom) with leather (a strong snow boot option) on the top. They’re both mid-calf length and...

The Snow Boot’s defining qualities:

  • You might expect to see laces strung through larger D-rings.
  • Potentially, but not necessarily, some sort of warm lining.

The Rain Boot’s defining qualities:

  • Traditional rainboots are made completely out of rubber.
  • They are smooth like a Ken Doll without any laces.

Brogue boots

Brogue Boots

The brogue boots are like if combat boots and work boots had a baby and that baby got dressed up in a tux to go to a fancy party. The brogue looks similar to a low-top dress shoe with a high top.

The Brogue Boot’s defining qualities:

  • Broguing — or those decorative perforations along the seams and on the tip — are the most obvious calling card of the style.
  • The soles can come in all styles: leather, lug, crepe, etc. etc.


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