For more than 30 years, Chatham Footwear has created shoes and boots that are well-suited to active lifestyles. The family-run business has its roots firmly planted in nautical and countryside life, and Chatham’s newest autumnal arrivals are precisely what you’ll need for getting out and about this season. From boggy dog walks to supermarket runs in the rain, these boots can handle anything that is thrown at them.
Cockley waterproof Chelsea boots
£170
Chatham took the Chelsea boot’s everyday style and made it more. More rugged, more hardwearing and, testing pending, more waterproof. The thick, cleated Vibrum rubber soles will keep you sure-footed through rain, snow, and muddy ground, while the Sympatex lining promises 100% waterproofing. We’ve not thoroughly tested that part out yet, but they certainly look like they will do the job well.
Inside, there’s a well-cushioned sole that is very comfortable underfoot, and the elasticated sides make them easy to grab and pull on, ready to head out.

Available in dark brown or tan, the uppers are made from premium leather, which is hardwearing and easy to clean (although we think the worn look adds some great character), so they should last for many seasons to come.
Windsor Women’s waterproof mid-calf boots
£210
There are plenty of stylish women’s boots around, but finding a pair that is as at home in a muddy wood as with a thick winter maxi dress is much more of a challenge. Windsor is a great addition to the Chatham Footwear range and fits both briefs nicely.
These mid-calf boots, made of tan-coloured premium leather, have a thick rubber sole to keep feet well insulated and dry. The waterproof Sympatex lining adds another layer of protection from the elements.


The Sole Spring Poron cushioning is soft yet supportive, so all-day wearing won’t fatigue feet, while the breathability of the materials will keep them feeling fresh.
Style details like the raised seams and side buckle elevate Windsor from run-of-the-mill waterproof boots to everyday essentials with style and character. A great-looking pair of boots that will undoubtedly become an easy-to-wear go-to choice.
What: Chatham waterproof autumn/winter boots
How much: from £170
Average Joes Rating: ★★★★★
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