We came across a pair of Timberland Graydon boots this week and we could not miss the chance to take a closer look and review its features. This model is one of the few sneaker boots from Timberland which sets it apart from the likes of White Ledge or Mt Maddsen that we’ve looked at recently. The brand has been experimenting for a while with such a design and the Graydon seems to have what it takes to be around for a while. From the looks of it it is pretty clear that Timberland wanted to have a stylish,affordable city boot in their lineup. The pair we got was one of the few colorways available, the one in brown and white. Out of the box the first thing you notice with these is how light they are given the leather construction and the fact that it is a Timberland shoe. This is because the boots have an overall slim silhouette, with thin leather upper and a low outsole. Size 9.5 weighs 11.5oz which is pretty outstanding even for a sneaker boot. 

How They Fit 

The Timberland Graydon boots fit true to size but they run a bit narrow in the toe box so those with wider feet may want to go at least half a size up. They are comfortable from the get go but they need a bit of break in period given the upper leather construction which is not the softest and the outsole which is not too flexible at the beginning.

Timberland Graydon brown white1

Timberland Graydon brown white4


The upper is made of leather material that has been treated to be water repellent. The leather is thinner than you would find at any of the other typical Timberland boots, likely to make the boots lighter and keep the cost low. They feature mesh material in the heel and tongue areas which are both lightly padded for a nice, cushy feeling. The boots come with Ortholite insoles which provide most of the cushioning and support. They feel ok at the beginning but they wear out after a while. The good news is that you can replace it with an even thicker one to add even more comfort. I walked around Chicago for this Timberland Graydon review and they did a good job in keeping my feet warm and comfortable in late November. 

Are Timberland Graydon Waterproof?

As mentioned previously the leather that these are made of has been treated to repel water with the proprietary Defender Repellent Systems. This comes in addition to the inherent waterproof  priorities of the leather. That does not mean, however, that they are fully waterproof like other boots from the brand, nor are they advertised as such. The tongue is not attached on the sides to the shoe so moisture will get in if you walk in deep snow. They are waterproof to an extent but proceed with caution, these are not the type of boots you can submerge your feet into a water puddle. 

Sole Unit 

The sole unit of the Timberland Graydon is very thin and simplistic, being made of a hardened EVA material. With these you get a very close to ground feeling which results in great stability. They do not provide much arch support, with the EVA insert being the main cushion in the sole. The outsole pattern makes it even more clear that they were made for the city streets rather than off trail trips. They provide decent traction for this purpose and they seem to be pretty durable. 

Timberland Graydon brown white2

Timberland Graydon brown white3

Bottom Line 

It was nice to try these on for my Timberland Graydon review. They are very stylish ,lightweight and easy to match with any everyday attire. These are perfect for those looking for a pair of modern city boots that can be worn casually or at office, mostly in the city. You can wear these at work but keep in mind that they do not provide much arch support so they are not ideal for standing up for long hours. They are quite versatile but they do not excel in other areas than in an urban setting. If taken care of properly they can last for a while, as long as you don’t treat them like hiking boots.