Verdict from 1 expert and +100 user reviews

9 reasons to buy

  • The Keen Grayson Chukka is an exceptionally comfortable sneaker-boot, based on several commenters.
  • Majority of buyers are happy about the durability of this shoe.
  • Many users find this shoe to be very good looking.
  • Some wearers can attest that the Keen Grayson is light on the foot.
  • The midsole support given by this shoe is appreciated by several reviewers.
  • A lot of people commend the stylish design of the Keen men’s Grayson Chukka.
  • Several sneakerheads like the cushioned footbed of this kick.
  • A good number of reviewers mention that this shoe looks good when worn with either business casual slacks or rugged jeans.
  • A few reviews mention that the leather used on this shoe is very soft. 

3 reasons not to buy

  • Most wearers are disappointed that it felt narrower compared to other Keen shoe models.
  • This shoe feels stiff at first and needs a bit of break-in time, based on some reviews.
  • Some complain about getting blisters in the heel area after wearing the Keen Grayson Chukka.

Bottom line

True to its claim, the Keen Grayson Chukka is a lightweight sneaker-boot that has a versatile style. It can be dressed up and down, depending on the user’s need. This shoe also received a lot of positive feedback for being comfortable, thanks to its cushioned footbed and soft leather upper.

Tip: see the best sneakers.

Good to know

Fit & Sizing

Despite its mid-top profile, the Keen Grayson Chukka offers a comfortable fit, thanks to its leather upper and footbed. Also, its fabric laces allow the users to customize the fit to their liking. 

The Keen Grayson Chukka is one of the high-top sneakers with a leather upper. Its handsome aesthetic can be smoothly transitioned from the office to a night out in town.  It has the right combination of being laid back and rugged. The shoe can be paired with jeans and shirt as well as khakis and button-ups. 

This high-top shoe features the Luftcell dual-density PU outsole that is responsible for its lightweight comfort. Also, it comes with sturdy metal eyelets and fabric laces for a secure fit.

Everyone who loves Keen shoes has Martin Keen to thank for for founding this globally acclaimed shoe manufacturing company. Keen has worked with popular shoe brands, such as Saucony and Timberland, as their shoe designer. Equipped with his skills and experience, he set out to design a hybrid shoe that can be comfortably worn on boats and outdoors.

In 2003, a shoe with a thick toe bumper was invented. That was the first ever Keen shoe. Most of the shoes from Keen have the iconic rubber toe bumper that works effectively in protecting the toes. These hybrid sandals also have a beefy outsole and a webbing pattern on the body.

When Keen shoes debuted in a 2003 shoe trade show, they were named as the Launch of the Year by the Footwear News. Despite being the subject of several fashion debates when it comes to style and aesthetic, Keen shoes have proven to be great shoe investments when it comes to outdoor activities. 

Aside from the hybrid sandals, Keen also released several other shoe designs and products, including cold-weather footwear, casual kicks, socks, and bags. Despite their increasing sales and international success, Keen has remained true to its roots in Portland. Their headquarter is stationed in Portland, thereby helping increase the economy of the state. Their first Keen Garage was also opened in Portland. 

What used to be a brand of outdoor shoes, Keen is slowly becoming a household name for casual wear. To date, the company has had hundreds of shoe, boot, flip-flop, and sandal models not only for men but also for women and kids.

One of their releases is the Keen Grayson Chukka. It still has the oversized toe bumper, but it has veered away from the peculiar style for its upper. The leather is fused directly to its insole, eliminating the need for shoe adhesives. 

  • The Keen Grayson Chukka weighs 467.8 grams.
  • Remove loose dirt and debris from the shoe by using a soft-bristled brush.
  • Rub a gum eraser in a circular motion to remove stains from the leather upper of this shoe.
Danny McLoughlin
Danny McLoughlin

Danny McLoughlin is a researcher for RunRepeat covering football, sneakers and running. After graduating with a degree in computer science from The University of Strathclyde, Danny makes sure never to miss a game of his beloved Glasgow Rangers or the Scotland national football team. He has been featured in prestigious publications such as The Washington Post, The Irish Times, Footwear News and the like.