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The Multipurpose Hiking Boot

The Multipurpose Hiking Boot

Sabir M. Peele of Men's Style Pro in Timberland Hiking Boots 22

Hiking boots aren’t usually your first footwear choice when thinking of a versatile shoe, however; the Heston waterproof boots by Timberland (w/ plaid Pendleton wool lining) changed that idea for me. With a sleek silhouette through the toe box and a rich reddish brown color leather, these boot can take you from the woods to the street, seamlessly. This is truly an instance where fashion & function meld perfectly.

Below I’ve style two looks to show the versatility of these hiking boot that might change your mind about all-terrain footwear. First up, Let’s Go Hiking!  


Into The Wild 


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Heston Waterproof Hiking Boots – Timberland | Orange Parka – Uniqlo | Cargo Jogger – Wallace & Barnes x J.Crew | Grey Knit Shirt – Zara | Bandana – Hav-a-Hank via A.C. Moore | Aviators – James Dean Eyewear | Warner (Dog) wearing Mesh Camo Harness – Puppia


Unless you’re Bear Grylls, you’re probably not a professional outdoorsmen. That means that copping a pair of hyper technical boots that you’ll only wear the once a year when isn’t a necessity.  Luckily from a technical standpoint these boots are equipped with Goretex™ waterproof technology,  Sensorflex™ technology which allow the shoe to flex while you’re leaping across a rocking creek and Ortholite™ comfort insoles. 

There are a slew of brands creating high fashion version of the hiking boot, however; they’re really made specifically city wear. So don’t expect those tech features that you see in these boots.

Up Your Hiking Style

  • Find the right pants. Hiking is the right time to pull out a pair of cargos. Remember, a tailored fit is still important, even in a pair of cargo pants.  A cargo jogger pant in a twill is perfect because they create a tight seal over your socks for added warmth. And, you can actually use your cargo pocket to harbor your cellphone or a pocket knife
  • Adding a brightly colored parka could save your life in the woods! With hunting season in full swing, you never want to get mistaken for a deer 
  • Besides adding stylistic flair, a bandanna can come in handy in a variety of ways. Are you sweating like a beast? Dab off with your bandanna.
    • Injure yourself and need to make a make shift tourniquet while waiting for medical attention? Use your bandanna
  • Wear a watch. Modern technology can fail you in the woods. Always Be Prepared!

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City Scape 


Sabir M. Peele of Men's Style Pro in Timberland Hiking Boots 5

Heston Waterproof Hiking Boots – Timberland | Plaid Wool Vest, Navy Turtleneck & Selvege Jeans – Uniqlo | Grey & White Flannel Gingham Shirt – Men’s Style Pro x Oliver Wicks | P51 Limited Edition Watch – Fossil | Red Cotton Braided Belt – J.Crew 


A pair of jeans is the hallmark of quintessential city style, however; hiking boots don’t traditionally fall into that style equation. Stylistically these Heston boots offers popping red laces, exposed Pendleton plaid lining and a sleek sole that make them a solid choice for a day or night out in the city.

See Also
Greene Street Consignment Gateway x Men's Style Pro

Why You Should Wearing Hiking Boots In The City

  • With a pair of worn in jeans, pairing a sleek hiking boot will make your outfit look more rugged and sporty (sans sneaker)
  • Kick Mother Nature’s Ass! Rain & snow is inescapable this time of the year. A waterproof hiking boot will keep your feet dry and provide some extra grip when the sidewalk is a slick
  • You can bring in elements of actual hiking style like a puffer vest. You’ll be paying homage to your somewhat outdoorsy lifestyle while staying warm

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Photography: Marina T. Peele @cantwinklefty

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