Verdict from 11 user reviews

8 reasons to buy

  • The majority of the reviewers are one in saying that the Timberland Cross Mark Waterproof Chukka delivers when it comes to comfort and style.
  • Many fans of Timberland sneakers express that the comfort level on this kick exceeds their expectations.
  • Plenty of individuals point out how this chukka keeps their feet warm and dry on rough and rainy weather.
  • Numerous wearers describe how this sneaker boot allows them to wear it dress up or dress down, much like the rest of the Timberland mid-cut shoes.
  • Most of the wearers notice that the overall construction of this Oxford boot is very durable.
  • According to a few testers, this sneaker requires only a short break-in period.
  • Many of the working people emphasize that this enables them to stand in long hours on feet comfortably.
  • The materials, quips many users, are made of premium quality.

3 reasons not to buy

  • Several reviewers share that this casual footwear feels narrow on the forefoot.
  • A couple of purchasers express their disappointment that this shoe is not available in the wide option. 
  • Some customers declare that the Cross Mark GTX Waterproof Chukka Boot easily gets dirty.

Bottom line

This waterproof mid-top version of the Timberland Cross Mark boasts of its versatility, making it easy to wear from the office to casual activities. Possessing quality craftsmanship with additional Gore-Tex® lining, this all-around chukka enables the wearer to brave the harsh city elements.

Superior cushioning is highlighted through the Aerocore™ Energy System, providing maximum comfort and flexibility.

Tip: see the best sneakers.

Good to know

The Timberland Cross Mark Chukka GTX® is exclusively available in men’s sizing only. Timberland uses a mid-top construction for added support and comfort.

Combining together the triple-cushioning Aerocore™ technology and the OrthoLite® detachable insole creates maximum comfort. Possessing breathable material and anti-microbial properties ensure a healthy feet environment.

At a glance, this sneaker boot looks similar to the Timberland Adventure Cupsole Chukka, especially the brown color variation. However, the midsole is one visible difference, where the Timberland Cross Mark GTX features the Aerocore™ cushioning.

The neutral color options in dark brown, wheat nubuck, and gray is well-received by shoe aficionados who either use this for work or laid-back shenanigans because one can easily match this with any outfit to match one’s purpose. 

Unassuming in design, this waterproof chukka boot makes a great match to any piece/s of clothing, especially when going about one’s grueling daily grind of rushing to a business meeting in khaki or doing personal errands in jeans.

One major stand-out detail of the Timberland Cross Mark WP Chukka is more felt than seen -- the revolutionary Gore-Tex® membrane. This internal lining is built into the shoe to create a breathable and water protection, keeping the wearer’s feet dry, while allowing sweat vapor to pass through. To identify this crucial feature is a metallic embellishment with an engraved “GORE-TEX” on the lateral heel side.

The trio cushioning combination of the textile-lined padded cuff and tongue, anti-microbial OrthoLite® footbed, and Aerocore™ technology keeps feet protected and supported at all times.

Originally known as the Abington Shoe Company in 1952, Timberland gained popularity in 1962 when it released the first waterproof cleats - more commonly known as the “6-inch Yellow Cleat” - by incorporating injection-molding technology. 

Due to its popularity and its waterproofing effectivity, the shoe manufacturer garnered a vast following and officially changed its name to The Timberland Company in 1978.

Deciding to expand to other footwear, Timberland started crafting sneakers that same year and has never stopped infusing the makeup of outdoor adventure in every design.

Part of the growing Cross Mark Collection, the Timberland Cross Mark GTX Waterproof Chukka Boot, is the only model with waterproofing features. Consistent across all designs is the durable urban outdoor vibe that the manufacturer is known for.

  • TPR (thermal poly rubber) welt with stitching details sits atop the midsole for added durability.
  • A tonal strip of leather with stitching details is visible on the tongue.

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.