The Multipurpose Hiking Boot

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 


Sabir M. Peele of Men's Style Pro in Timberland Hiking Boots 26

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 


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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.

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

Sabir M Peele

Founder & Creative Director

Founder & Creative Director of Men's Style Pro, Sabir has a deep passion for menswear and all things manly. Selected as one of the "5 Best Dressed Men In America" by Esquire Magazine in 2010 & as #GQFall 2013 Best Dressed Man. As of 2014, Sabir serves as a freelance brand ambassador & executive stylist for GQ Magazine & GQ Report. Outside of that partnership, Sabir serves as an independent brand consultant as well. Reach me directly at SABIR@MENSSTYLEPRO.COM

  • sanochu

    Wow, great idea! I never thought of looking for style in my hiking boots.. Thank you for these great advices!

  • DJ

    Both hiking boots work boots are actually two of my favorite styles. Chelsea boots of course look the best aesthetically, but there’s nothing better comfort wise than a pair of boots like these with rolled up jeans/chinos. Still looks just as good to me

    DJ | http://www.collegestyleguy.com

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