Winsor Trail Outdoor Hiker For Men

Winsor Trail Outdoor Hiker For Men

Sale price R 2,240.00
Regular price R 3,199.00
Tax included. Shipping calculated at checkout.
Size (UK/SA)
Low stock - Selling Fast!
This men's hiker is designed for getting you outside and getting you moving. This outdoor-inspired casual hiker features enhanced grip on the outsole combined with the comfort of our GreenStride technology. The GreenStride sole foam is made using an EVA blend including 75% biobased materials derived from sugar cane and responsibly grown rubber. The boot is designed to be comfortable and supportive on any terrain. Timberland also supports responsible manufacturing of leather via the Leather Working Group.

Men's Footwear Size Chart

Not sure what size to choose? Find your perfect fit with our size guide.

6 6.5 39.5 24.5 
6.5 7 40 25
7 7.5 41 25.5
7.5 8 41.5 26
8 8.5 42 26.5
8.5 9 43 27
9 9.5 43.5 27.5
9.5 10 44 28
10 10.5 45 28.5
10.5 11 45.5 29.5
11 11.5 46 30
11.5 12 47.5 31
12.5 13 49 32


At, our goal is simple: We want you to feel as confident in your order as we do in our product. And you can, because we stand behind each product we make. If you require further assistance, reach out to us at

Upper in premium nubuck leather
Timberland supports responsible leather manufacturing through the Leather Working Group
Upper detailing and lining in durable ReBOTL™ fabric, containing at least 50% recycled plastic
GreenStride™ sole foam made using an EVA blend including 75% biobased materials derived from sugar cane and responsibly grown rubber
Lightweight and breathable OrthoLite® footbed
Protective rubber rand
Rubber lug outsole for gip

CleanerRenewbuck® Suede and Nubuck Foam CleanerSuede Restorer BrushDry Cleaning KitProtectorBalm Proofer™ All Purpose ProtectorSneaker Care Kit

We offer free shipping on all orders, and our standard delivery time is 5-7 working days.

Please note that deliveries are only made Monday to Friday, excluding weekends and public holidays.

Please be aware that delivery times may vary depending on your location and any unforeseen circumstances outside of our control that may occur. If you have any concerns or questions about your shipment, our customer service team is available to help Monday to Friday between 10am and 5pm.





Customer Reviews

Based on 4 reviews
Malesela Phihlela (Pretoria, ZA)
Winsor Trail outdoor hiker

Very comfortable and stylish.

Thamsanqa Manzana (Johannesburg, ZA)
Nice quality shoes

Nice quality shoes

Kabelo (Johannesburg, ZA)
Wrong size

They shipped wrong size. Disappointed

Brookes Makhongwane (Meyerton, ZA)

This is my 5th pair of Timberland since last year October and I know their quality standard.
With Timberland you will never go wrong and the online service is also quick and cost efficient, it also saved my time, thank you Timberland.

Wear it your way