New Yorkers Are Obsessed With These Classic Boots—9 Ways to Wear Them in 2024

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(Image credit: @malonnie.j)

When we all made our "ins and outs" lists for 2024, I listed "closet staples" as in and "one-time wear" as out. And nothing says "closet staple" quite like a pair of Timberland boots. For 50 years (literally), these shoes have reigned supreme among native New Yorkers and transplants alike as the quintessential city boot that anyone can wear in any kind of weather to just about any job. New York City is one of the most unpredictable places, but one thing I can always count on is spotting a pair of Timberland original six-inch work boots on the subway, in the park, or at the crosswalk. Even when I don't spot them on my daily commute, I see them in paparazzi photos of Jennifer Lopez, Rihanna, and Emily Ratajkowski. As corny as it sounds, I feel most like a New Yorker when I'm wearing a pair of Timberland boots.

Cult-classic status clearly isn't enough for the team at Timberland because they continuously launch new and exciting variations of this iconic shoe, including collaborations with Jimmy Choo and Veneda Carter and an upcoming collab with Louis Vuitton. Let's just say Timberland already has all of my attention (and money) in 2024. My latest obsession is the Indigo Suede Icons Collection in partnership with C.F. Stead, a renowned English tannery best known for producing the world’s finest leathers and suedes. These are comfortable, waterproof, and the perfect twist on the original yellow boots. You're going to continue to see these shoes dominate this year, so I figured I'd leave you with some inspo. If you're looking for fresh ways to style Timberland boots that feel so 2024, just keep scrolling.

But First, Fur

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(Image credit: @anetegludite)

How to style: Oversize fur coat + white tee + baggy, medium-wash denim

All in on Overalls

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(Image credit: @nataliegrayherder)

How to style: Denim overalls + structured wool coat + baseball cap

Back on Track

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(Image credit: @malonnie.j)

How to style: Faux-leather jacket + track pants + leather purse

Put It in Neutral

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(Image credit: @indyabrown)

How to style: Trench coat + white oversize button-down shirt + white cotton midi skirt

Next-Level Layers

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(Image credit: @lunaklestrup)

How to style: cobalt-blue sweater + wool coat + trench coat + dark-blue denim + oversize sunglasses

The Gr-outfit

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(Image credit: @aniyahmorinia)

How to style: Gray cardigan and knit skirt set + gray coat + mini crossbody bag

Cabin Chic

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(Image credit: @danie.sierra)

How to style: oversize cable-knit sweater + vintage denim + printed beanie

Denim Diary

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(Image credit: @courtneyhollins)

How to style: Dark-wash denim jacket + light-wash straight-leg jeans

Cue the Comfort

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(Image credit: @badkidhq)

How to style: Bomber jacket + parachute pants + cashmere sweater + beanie

Aniyah Morinia
Associate Branded Content Editor
Aniyah Morinia is an NYC-based associate beauty and fashion editor at Who What Wear. She has worked in fashion media since 2018 and joined WWW's branded content team, where she not only writes for some of her favorite brands but also creates content for them. Aniyah will find any excuse to get a photo of her outfit and absolutely loves taking photos. She graduated from the University of Florida in 2020 with a bachlor's degree in public relations and started post-grad life freelancing for EveryStylishGirl, Riot Swim, and Baby Tress. Since starting at Who What Wear, Aniyah has developed a passion for hosting livestreams, working red carpets, and creating TikToks in addition to writing fashion and beauty stories. When Aniyah's not writing or creating content, you can find her exploring Brooklyn and eating her way through the city. She'll never pass up the opportunity to uncover an NYC hidden gem or mix and mingle with her friends (all while swapping holy-grail products, of course).