We spent 9.4 hours reading reviews from experts and users. In summary, this is what sneaker fanatics think:

8 reasons to buy

  • The Timberland Bradstreet Chukka provides excellent comfort for the foot, as most of the reviewers have said.
  • Many users have claimed that they love the quality of the shoe as it is quite durable.
  • The shoe feels lightweight, according to some of the purchasers.
  • Like other Timberland Bradstreet iterations, it has a stylish design that is appreciated by a good number of buyers.
  • Several reviewers are highly appreciative of the shoe being weatherproof.
  • A lot of the buyers say that they would recommend this kind of Timberland shoes to others.
  • A buyer can choose among the various colorways offered for the shoe.
  • The shoe fits true to size, as per most buyers.

3 reasons not to buy

  • The Timberland BradstreetChukka is offered at a slightly expensive price.
  • A couple of users have complained that the shoe is hard to clean.
  • A few buyers have said that there was a squeaking sound in the soles of the shoe.

Bottom line

A line of work cleats that successfully shifted into casual footwear is what the Timberland brand also offers. Among these shoes is the Timberland Bradstreet Chukka. Though this mid-top footwear wraps the foot in great comfort as well as keeps the foot protected from different weather types. It also displays a stylish appeal that suits best with one’s trendy style.


Top: Mid
Inspired from: Hiking
Collection: Timberland Bradstreet
Closure: Laces
Material: EVA, Leather, Nubuck, Rubber Sole
Price: $135
Colorways: Beige, Black, Blue, Brown, Green, Grey, Multi, Red, Yellow
Small True to size Large
Tight Loose
Neutral Stable
Stiff Flexible
Warm Breathable
Firm Plush
Durability 9/10
Comfort 9/10
Traction 9/10
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A top rated sneaker
A top rated Timberland sneaker
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The Timberland BradstreetChukka is a mid-top silhouette that features the lace-up closure system that offers the wearer the opportunity to lock down their foot in a snug yet comfortable fit. It is available in men’s sizing. 

Though Timberland originally created shoes to provide hardworking outdoorsmen quality work cleats that meet their needs, the brand has successfully transitioned their work cleat silhouettes into casual fashion footwear.

The Timberland Bradstreet Chukka displays a combination of functional and aesthetical appeal with its design. The clean and sleek look of this mid-top shoe offers the wearer a trendy appeal that would suit different attire choices.

The shoes may be best with a pair of regular jeans, fitted jeans, cuffed jeans, chinos, and combats. Women may be creative and fun and pair the shoe with a pair of skinny jeans or with the kind dress that would suit and match it best.

The clean and sleek design of the Timberland Bradstreet Chukka is what carries the image of the silhouette. The less bulky appearance of this mid-top shoe adds more to its stylish appeal, keeping it on-trend. It also allows the shoe to be able to match with different attire combinations.

Way back in 1933, the beginning of the company’s history, it was then known as the Abington Shoe Company which produced wholesale hand-stitched shoes. In 1952, half of the company was bought by Nathan Swartz and continued to do contractual works with other manufacturers. By 1955, he bought the other half of the company as he saw its potential.

In 1965, the company incorporated injection-molding in constructing their shoes which makes their shoes waterproof. By the year 1965, the company was moved to Newmarket, New Hampshire. It was in 1973 that the company made a name change from Abington Shoe Company to Timberland Company.

Also in 1973, the classic and iconic Timberland 6 Inches Work Cleats was first introduced to the world. It was originally designed as working cleats for blue-collar workers. During the ’90s, a peculiar thing happened around New York City as rappers, and the likes began wearing the cleats as a part of their cultural outfit.

Timberland said that during the 90’s their sales more than tripled as their cleats became a significant part of the hip-hop and urban culture. It was the 6-inch-boot that the 90’s era was all about. The silhouette can be seen on the foot of Das EFX, Mobb Deep, DMX, Notorious B.I.G., and Kanye West. They rocked the shoes in both their videos and performances. Soon, almost everyone is rocking the cleats, and it made the silhouette to enter the fashion world successfully.

At first, Timberland tried to disassociate itself from their new market and their new street identity, and they tried to deter the cleats fans. But soon they realized that the cleats’ new credentials couldn’t be denied, and they accepted it with open arms. Now, the cleats have become a significant part of modern fashion.

Timberland started to create more silhouettes that still displays the brand’s roots and elements, and its classic and signature design. Among these is the Timberland BradstreetChukka which features a sleek yet trendy design that fits perfectly with both the semi-formal and street-style appeal. Aside from the traditional tan leather, the brand also produced more colorways for the silhouette, allowing the buyers to have more options that would suit their taste best.

  • The minimal rubber pods of the Timberland BradstreetChukka are made of Green Rubber compound which is 42% recycled rubber.
  • The laces of the shoe are 100% organic cotton.
  • The lining and the footbed cover of the shoe are made of extra soft 100% recycled PET.
  • The upper of the shoe is covered with premium full-grain and nubuck leather which is from an LWG Silver-rated tannery.
  • A padded collar can be observed on the shoe.
  • The signature Timberland logo is displayed on the sides by the heel of the shoe.


Danny McLoughlin

Danny is a sneakerhead turned sneaker industry expert that believes a good outfit begins from the feet up. His aunt currently isn't speaking to him for wearing a pair of kicks at his cousin's wedding. He spends most of his time trying to keep on top of the latest releases, hitting up his contacts and doing what needs to be done to secure his next pickup. Danny has been featured in prestigious publications such as The Washington Post, The Irish Times, Footwear News and the like.