4 Best Timberland Sneakers For Men, 20+ Shoes Tested in 2023

Sheena on

No matter your station in life, whether you belong to a fashion-savvy society or a regular dude working in the construction business, the men’s Timberland sneakers are a favorite casual or streetwear staple that are beloved by many in the active lifestyle shoe scene.

Since its inception in the 1950s in Boston, Massachusetts, Timberland has built an amazing collection of hiking-inspired lifestyle shoes that deliver excellent versatility and comfort, allowing you to socialize and attend formal events, and then go for a short hike in the local park thereafter.

We considered 10+ pairs of the best men’s Timberland sneakers currently available out there. We picked our favorites in the bunch that really stood out based on our rigorous performance tests. Check out the top picks below.

How we test sneakers

We identify the stand-out models from the Timberland brand through a meticulous analysis. The whole process involves a thorough go-over inside our independent RunRepeat shoe lab. After which, the wear-testing team takes over by subjecting all the sneaks to the acid test of wear and tear usage.

The entire procedure includes:

  • Putting in the hours and our personal resources to perform all the tests. This means buying the men’s sneakers from Timberland from our own pocket to ensure complete objectivity.
  • Wearing the sneakers to thoroughly assess their material quality, actual fit and comfort, support, outsole traction, durability, versatility, and a lot more.
  • Slipping into the shoes for all-day wear at work, or donning the kicks in more formal environments. We take note of the sneaker’s strengths and weaknesses.
  • Scouring multiple sources on the internet to gather more data from customer reviews and expert opinions.

To end this guide, we give each pair of the men’s Timberland sneakers its final rating. Check the CoreScore to view all the ratings of the models in the selection.

Best men's Timberland sneakers overall

Timberland Bradstreet Ultra Oxford
Timberland Bradstreet Ultra Oxford


4.8 / 5 from 78 users


  • Clean and sharp look
  • Versatile for casual wear
  • Keeps feet cool on hot days
  • Super lightweight
  • Grippy for different surfaces
  • Supportive and stable
  • Supple upper of leather variant
  • No break-in time


  • Dark colorways stain badly
  • Not well-cushioned
  • Pricey


The Bradstreet Ultra Oxford from Timberland makes great casual looks as easy as 1-2-3. With its sleek look, it matches different casual styles exceptionally well, elevating outfits with a subtle classy vibe. In addition, it has everything needed to stand with poise, refinement, and composure for any occasion.
Timberland Bradstreet Ultra Oxford full review

Best Timberland mid top sneakers for men

Timberland Groveton Chukka
Timberland Groveton Chukka


4.5 / 5 from 5,151 users


  • Classy silhouette
  • Gets compliments galore
  • Quality materials and construction
  • Super lightweight
  • Great durability
  • Breaks in fast
  • A good investment


  • Upper is prone to stains
  • No arch support


The Groveton Chukka from Timberland is a shoe that blows away people’s expectations of it. While many have bought it for a specific purpose, it has quickly become an everyday shoe for them because of the sheer amount of style and utility it brings to the table. In addition, its quality construction means that its brilliant looks and refined feel are here to stay.
Timberland Groveton Chukka full review

Best value

Timberland Davis Square Mixed-Media Chukka
Timberland Davis Square Mixed-Media Chukka


4.5 / 5 from 11,182 users


  • Perfect balance of style
  • Comfortable for all-day wear
  • Timeless and clean look
  • Runs true to size
  • Lightweight
  • Unique construct
  • Easy to style
  • Matches any outfit


  • Causes blisters
  • Lacks cushioning
  • Narrow


This Timberland Davis Square Mixed-Media Chukka has treated nubuck repels oil, water, and stains, while the Cordura® fabric resists abrasions. This mid-profile sneaker boot features eco-friendly materials of Cordura® EcoMade fabric and soft fabric lining made from recycled plastic bottles.
Timberland Davis Square Mixed-Media Chukka full review

Sheena is a wordsmith turned sneaker addict. Her sneaker fixation intensified as her passion for writing grew. A hands-on mom of two sweet yet spunky kids (plus three dogs and two cats), she finds solitude in leafing through shoe catalogs to find the next "it" sneaker. Scrutinizing hugely popular and underrated kicks is her favorite pastime.