How to Style Timberland Boots

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The verdict is in: Timberland boots are an instantly timeless piece for your wardrobe, whether you’re aiming for rugged casual or polished streetwear. With the right pairing of clothes and accessories, Timberlands can effortlessly elevate any fit while maintaining their heavy-duty appeal. Plus, welded seams and weatherproof features keep feet dry and comfy whether you’re walking through snow, stomping in puddles, trekking up a hill or dancing in the club. Yeah, they’re great work boots, too, but here’s how to style Timberlands for the everyday wear or those special occasions.

Street Smart

Pair your men’s classic Wheat Nubuck Timberlands with slim-fit jeans or joggers for a laid-back vibe. Layer on a hoodie or oversized sweatshirt in neutral tones like black, gray or navy. For extra edge, top it off with a bomber or denim jacket.
Or wear Timberland boots with a cropped sweatshirt or graphic tee for a streetwear feel. Finish the look with an oversized coat, plaid shirt or distressed denim jacket. Sunglasses and bold makeup, like a red lip, can enhance the edgy aesthetic.

The Mountains Are Calling

You don’t have to be a mountaineer to style those Timberlands like you’re going on some grand adventure. Stay outdoor adventure-ready with waterproof “Espresso” Timberland boots paired with cargo pants, flannel shirts, and a puffer or utility jacket. Layer with a thermal undershirt for extra warmth. This practical look is perfect for hiking or exploring, providing both comfort and style.

Workwear-Inspired Aesthetic

Women’s Timberland boots and wide-leg jeans or cargo pants, along with a cozy cardigan and tucked-in fitted tee give off an eclectic vibe. Wear this versatile look to class, to work or just out for dinner for a trendy take on workwear. For a similarly relaxed but more polished look, men can style Timberland boots, like the Field Mid Lace-Up waterproof style, with a button-up shirt and tailored denim pants or cargos. Add a quarter-zip or full-zip jacket for a little more prep in your step.

Flowy Yet Chic

Contrast the light ruggedness of Timberland chukka boots with a soft, flowy dress or skirt. A floral or pastel dress with tights works well for fall or winter. Add a leather or suede jacket for a chic, layered look. Accessories like a scarf or minimalist jewelry can further soften the look.

Styling Timberland boots is simple with the help of Hibbett. Shop our online selection of men’s and women’s styles, or visit us in stores.