Search  for anything...

Timberland Men's Graydon Sneaker Boot

  • Based on 1,308 reviews
Condition: New
Checking for the best price...
$88.00 Why this price?
Save $12.00 was $100.00

Buy Now, Pay Later


As low as $14.67 / mo
  • – 6-month term
  • – No impact on credit
  • – Instant approval decision
  • – Secure and straightforward checkout

Ready to go? Add this product to your cart and select a plan during checkout.

Payment plans are offered through our trusted finance partners Klarna, PayTomorrow, Affirm, Afterpay, Apple Pay, and PayPal. No-credit-needed leasing options through Acima may also be available at checkout.

Learn more about financing & leasing here.

Selected Option

Free shipping on this product

This item is eligible for return within 30 days of receipt

To qualify for a full refund, items must be returned in their original, unused condition. If an item is returned in a used, damaged, or materially different state, you may be granted a partial refund.

To initiate a return, please visit our Returns Center.

View our full returns policy here.


Availability: Only 3 left in stock, order soon!
Fulfilled by Amazon

Arrives Wednesday, Aug 6
Order within 3 hours and 25 minutes
Available payment plans shown during checkout

Color: Wheat Full-grain


Size: 12


Description

Made to be super comfortable with an OrthoLite Impressions memory-foam footbed and the Hoverlite comfort outsole, these men's chukka boots are also responsibly constructed with environmentally sensitive materials.

Department ‏ : ‎ mens


Date First Available ‏ : ‎ May 20, 2025


Best Sellers Rank: #237,401 in Clothing, Shoes & Jewelry (See Top 100 in Clothing, Shoes & Jewelry) #115 in Men's Chukka Boots


#115 in Men's Chukka Boots:


Customer Reviews: 4.5 4.5 out of 5 stars 1,308 ratings


Frequently asked questions

If you place your order now, the estimated arrival date for this product is: Wednesday, Aug 6

Yes, absolutely! You may return this product for a full refund within 30 days of receiving it.

To initiate a return, please visit our Returns Center.

View our full returns policy here.

  • Klarna Financing
  • Affirm Pay in 4
  • Affirm Financing
  • Afterpay Financing
  • PayTomorrow Financing
  • Financing through Apple Pay
Leasing options through Acima may also be available during checkout.

Learn more about financing & leasing here.

Top Amazon Reviews


  • Functional Life Style
Color: Wheat Full-grain Size: 11
I really enjoy these shoes. They are lightweight and comfortable. I can walk around all day in them and when at a gathering with family and friends it allows me to be athletic and stylish. I can dress them up and dress them down, very functional and fitting to my life style.
Reviewed in the United States on June 10, 2025 by Jonathan Townsend

  • Casual/Dress shoes
Color: Wheat Full-grain Size: 11
I love these shoes! I wear them with my suits and casual apparel. I bought the black ones too. Fit perfect and are very comfortable. I also love that my dress pants fit perfectly over them.
Reviewed in the United States on December 18, 2024 by Jason Kallam

  • NOT your Avg looking ortho kicks!
Color: Black Nubuck Size: 9
Purchased for a family member who has neuropathic pain due to chemotherapy, arthritis and chronic back pain. We’ve tried every conceivable shoe/sneaker combination and had little luck finding anything that’s made much of a difference. It’s too early to know if these are going to make him more comfortable but the pros are they are ULTRA light weight. They have a memory cushion insole and good support. They also don’t look like orthopedic shoes, which is a bonus. And, supposedly waterproof. They are sturdy construction so fingers crossed.. but so far, so good. ... show more
Reviewed in the United States on October 25, 2023 by iamkristinc

  • Much shorter height wise than the picture.
Color: Black Nubuck Size: 10.5
The picture was quite deceiving, they look taller. I bought these specifically for motorcycle riding, so I was hoping they would be taller. However they do have decent ankle support. Very light weight, and grippy on metal bike pegs. Wish I would have gotten a half a size bigger but they feel nice overall. The laces haven't come untied yet with a double knot. ... show more
Reviewed in the United States on June 8, 2025 by Eric Mattox

  • Good buy
Color: Wheat Nubuck Size: 10
Good quality husband was happy
Reviewed in the United States on June 6, 2025 by miranda

  • Amazing and comfy
Color: Black Nubuck Size: 12
I’ve worn timberlands exclusively for years and these are one of the best pairs I have ever owned
Reviewed in the United States on July 21, 2024 by Owen Files

  • Worth the money, comfy, great looking!
Color: Black Nubuck Size: 12
Usually don’t take the time for reviews but these boots deserve one. I’ve worn them for just about a week now and a huge fan so far. I work in the office half the time but also out in the field from time to time to do site visits and wanted something that was good looking, light, comfy, but also had some ankle support. These are perfect! I don’t believe they are waterproof but definitely water resistant and used in a few inches of snow with some wool socks and didn’t have any issues with feet getting wet. Was nervous about the fit and wasn’t sure if they were true to size. But they definitely are spot on! Definitely recommend if you’re looking for a nice lightweight boot/sneaker that is comfy, stylish and useful. Will update in a month or two for the durability factor. ... show more
Reviewed in the United States on March 14, 2020 by Josh

  • Good looking but not comfortable
Color: Wheat Full-grain Size: 10.5
This shoes are not meant for walking, which is too bad… The leather is high quality, the stitches and sole as well. But to walk in this shoes is a real challenge
Reviewed in the United States on October 3, 2024 by Kateryna

Can't find a product?

Find it on Amazon first, then paste the link below.
Checking for best price...