Verdict from 20 user reviews

6 reasons to buy

  • Light: Compared to other sneakerboots, the Timberland Davis Square Chukka will not weigh you down.
  • Instant comfort: Lots of reviewers say that this shoe offers cozy strides from day one.
  • Versatile: "The perfect casual shoe," this chukka boot can be worn for work, outings, and even date nights. One even used this as his motorcycle boot.
  • Stylish: Many Timberland fans like the shoe's look which they described as "dope" and "fire."
  • Supportive: Its mid-top construction keeps the ankles from twisting.
  • Warm: Feet feels snug and toasty making this hiking-inspired kick a great cold-weather season boot. 

1 reason not to buy

  • Uneven stitching: One was bothered by the lumpy seam inside one of the boot's.

Bottom line

Timberland has always impressed sneakerheads with its collection of rugged yet fashionable kicks. And Timberland's Davis Square Chukkas are no exception. Its streamlined styling and homey interiors make this sneakerboot the perfect choice for busy gals and guys. What's more, it's made of recycled materials. 

Tip: see the best sneakers.


How Timberland Davis Square Chukka Boots ranks compared to all other shoes
Top 29% sneakers
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Top 24% Timberland sneakers
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Top 27% mid sneakers
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The current trend of Timberland Davis Square Chukka Boots.
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Danny McLoughlin
Danny McLoughlin

Danny is a sports nut with a particular interest in football and running. He loves to watch sports as much as he loves to play. Danny was lead researcher on RunRepeat and The PFA’s report into Racial Bias in Football Commentary. His football and running research has been featured in The Guardian, BBC, New York Times and Washington Post.