This sporty lace-up shoe is from the well-known Timberland brand. Crafted from premium nubuck leather, the Timberland Bradstreet Chukka features a comfortable lining that lets your feet breathe and is made from 100% recycled materials. The shoe is equipped with a special SensorFlex technology that provides good support, as well as optimal suspension and flexibility. It is completely waterproof thanks to the Gore-Tex membrane and the shoe also has an OrthoLite PU footbed. This footbed offers cushioning and extra support while walking. The shoe also has durable laces that are made from recycled materials, is lightweight and has a soft edge for extra comfort. The sturdy rubber sole offers you a good grip on all surfaces. The Timberland Bradstreet Chukka is the ideal combination of style, comfort and quality.
This sporty lace-up shoe is from the well-known Timberland brand. Crafted from premium nubuck leather, the Timberland Bradstreet Chukka features a comfortable lining that lets your feet breathe and is made from 100% recycled materials. The shoe is equipped with a special SensorFlex technology that provides good support, as well as optimal suspension and flexibility. It is completely waterproof thanks to the Gore-Tex membrane and the shoe also has an OrthoLite PU footbed. This footbed offers cushioning and extra support while walking. The shoe also has durable laces that are made from recycled materials, is lightweight and has a soft edge for extra comfort. The sturdy rubber sole offers you a good grip on all surfaces. The Timberland Bradstreet Chukka is the ideal combination of style, comfort and quality.
in 2 offers
The lowest price for Timberland Bradstreet Chukka Boots, Brown, Size 43 right now is $188.78 at 4Feetshoes.
The all-time low was $155.49 on 30 Sept 2024 — today's price is 21% above the lowest ever. It has been notably cheaper before — worth setting a price alert.
Prices last updated 7 May 2026.
Timberland Bradstreet Chukka Boots, Brown, Size 43
This sporty lace-up shoe is from the well-known Timberland brand. Crafted from premium nubuck leather, the Timberland Bradstreet Chukka features a comfortable lining that lets your feet breathe and is made from 100% recycled materials. The shoe is equipped with a special SensorFlex technology that provides good support, as well as optimal suspension and flexibility. It is completely waterproof thanks to the Gore-Tex membrane and the shoe also has an OrthoLite PU footbed. This footbed offers cushioning and extra support while walking. The shoe also has durable laces that are made from recycled materials, is lightweight and has a soft edge for extra comfort. The sturdy rubber sole offers you a good grip on all surfaces. The Timberland Bradstreet Chukka is the ideal combination of style, comfort and quality.
This sporty lace-up shoe is from the well-known Timberland brand. Crafted from premium nubuck leather, the Timberland Bradstreet Chukka features a comfortable lining that lets your feet breathe and is made from 100% recycled materials. The shoe is equipped with a special SensorFlex technology that provides good support, as well as optimal suspension and flexibility. It is completely waterproof thanks to the Gore-Tex membrane and the shoe also has an OrthoLite PU footbed. This footbed offers cushioning and extra support while walking. The shoe also has durable laces that are made from recycled materials, is lightweight and has a soft edge for extra comfort. The sturdy rubber sole offers you a good grip on all surfaces. The Timberland Bradstreet Chukka is the ideal combination of style, comfort and quality.
Last updated at 07/05/2026 23:03:23
Timberland A1989 Bradstreet Chukka Boot In Wheat For Men
Delivery $19.20
Timberland A1989 Bradstreet Chukka Boot In Wheat For Men | 8.5 UK - 43 EU - 9 US
Delivery $13.71
originally posted on shopee.sg
Value for Money:GoodQuality:GoodWearing Comfort:Very comfortableNote as this is not wide fitting, those have wide foot may consider to order half or one size bigger. I order half size bigger and is JUST nice for fit my wide foot. As expected, 1st wear cause blister on wider end of my foot. After that it's fine already.
originally posted on timberland.co.uk
These are the right size shoe, they are light and comfortable but need breaking in.Also worth noting, the colours shown on these shoes is completely inaccurate.Grey is not dark grey as shown in the photos. Actual shoes are a lot lighter more accurately mid grey, which could be questionable with Darker jeans. Unfortunately these are the only colour that comes with a black sole.May return for a darkest brown or black.
originally posted on timberland.co.uk
I kept checking for a grey 10.5 Mens great size for a couple of weeks on the site and brought them straight away when I revived a notification from Google lolHesitant as buying an online product after reading reviews but I believed in the brand. When I revived them couldn't be happier ! Wearing them on every occasion during winter and thinking about a second pair already! LolI've recommended to their friends who've brought online too in time for Xmas.Revived our orders in nicely presented bixes and prompt delivery too
| Cut | Mid cut |
Timberland A1989 Bradstreet Chukka Boot In Wheat For Men
Delivery $19.20
Timberland A1989 Bradstreet Chukka Boot In Wheat For Men | 8.5 UK - 43 EU - 9 US
Delivery $13.71
Value for Money:GoodQuality:GoodWearing Comfort:Very comfortableNote as this is not wide fitting, those have wide foot may consider to order half or one size bigger. I order half size bigger and is JUST nice for fit my wide foot. As expected, 1st wear cause blister on wider end of my foot. After that it's fine already.
These are the right size shoe, they are light and comfortable but need breaking in.Also worth noting, the colours shown on these shoes is completely inaccurate.Grey is not dark grey as shown in the photos. Actual shoes are a lot lighter more accurately mid grey, which could be questionable with Darker jeans. Unfortunately these are the only colour that comes with a black sole.May return for a darkest brown or black.
I kept checking for a grey 10.5 Mens great size for a couple of weeks on the site and brought them straight away when I revived a notification from Google lolHesitant as buying an online product after reading reviews but I believed in the brand. When I revived them couldn't be happier ! Wearing them on every occasion during winter and thinking about a second pair already! LolI've recommended to their friends who've brought online too in time for Xmas.Revived our orders in nicely presented bixes and prompt delivery too
I got these recently together at the same as another much cheaper pair of similar looking boots.These were far more comfortable and smart looking (there's a reason Timberland are a well-known brand). I was out all day in them walking around town, and didn't feel any discomfort at any point.One bit to be aware of: I normally wear size 9 trainers, but the size 9 boots were massive. I went for the 8.5 instead.
I saw these online and instantly wanted a pair.. they are a great fit and do comfortable with the quality you expect from Timberland. Delivered quickly, very impressed with the service, so much so I will be buying another pair, different colour of course. 10/10
First month of wearing was absolutely fine, I had no issues. But after week 5 or so, I started to notice wearing around the padding, at the ankle. I thought this was really strange, considering I had only had these for several weeks. Around 6 weeks in and the threading around the ankle has completely come loose.I now have zero support around the ankle, which makes my foot constantly slip up and down inside the shoe when walking. It's also an eye sore, as the padding sticks out and just looks unsightly. I use these regularly, but only for general walking. I could understand if I was hiking in these everyday.I was really happy up until this point which is such a shame. This is my first time purchasing a Timberland Chukka and my first impression are one of ... MoreFirst month of wearing was absolutely fine, I had no issues. But after week 5 or so, I started to notice wearing around the padding, at the ankle. I thought this was really strange, considering I had only had these for several weeks. Around 6 weeks in and the threading around the ankle has completely come loose.I now have zero support around the ankle, which makes my foot constantly slip up and down inside the shoe when walking. It's also an eye sore, as the padding sticks out and just looks unsightly. I use these regularly, but only for general walking. I could understand if I was hiking in these everyday.I was really happy up until this point which is such a shame. This is my first time purchasing a Timberland Chukka and my first impression are one of disappointment. I had always associated this brand and their products, with long lasting quality, that really stand the test of time. Clearly, I was wrong.
18 years ago I broke my back in a motorcycle crash and I have drop foot in both feet as a result of my troubles. I have to wear AFO's to walk and 3/4 years back Otto Bock invented the GoOn ankle-foot orthosis, great if you have drop foot. My next challenge was finding the right shoes to wear with them, I tried trainers, shoes, boots and I eventually purchased a pair of Bradstreet Chukka boots - wow. they are so comfortable, the highish ankle offers me additional support and the number of eyelets means my AFO's are properly secured in the shoe. They also keep my feet warm and dry. I will now only wear these boots and will be buying more pairs in the coming months - just in case Timberland stop making them :)
These are great boots. Several reviewers appear to be giving a poor ratings based on their perception of size and colour. I'm a 9 in Lacoste, 8.5 in Timberland and 8 in Clarks and Sketchers! You can't blame Timberland for that. Also, Bradstreet comes in at leat 8 colours so you need to research this. If you find your boots are too big or the wrong shade of brown you only have yourself to blame! I have 2 pairs of these, great quality and comfortable.
| Cut | Mid cut |
