British winter has a way of finding every gap in your footwear. One wet walk and you learn the difference between boots that look waterproof and boots that actually are. With the rainy months ahead, here's what we'd check before buying a pair that has to earn its keep.
Check the waterproofing, not just the look
"Water-resistant" and "waterproof" aren't the same thing. A proper waterproof boot uses a membrane and sealed construction — our Chicago Waterproof Boots (£129.00) use a Wil-Tex waterproof membrane with a gusseted lace system, so rain stays out from every angle, not just the top.
Comfort decides whether you wear them
The warmest, driest boot in the shop is useless if it lives in the hallway. Look for cushioned, removable insoles (handy if you use your own orthotics), a padded collar that doesn't bite the ankle, and a fit you can adjust — speed-hook lacing and a rear pull loop make the Chicagos easy to get on and off when your hands are cold. They're made in soft Italian suede, in EU sizes 36 to 42.
Match the boot to the walk
For school runs and town errands, a shorter boot is easier to live with. For muddy dog walks and country paths, you want the full weather protection and grip. Think honestly about where your boots will spend most of their time — the right pair for a commute isn't always the right pair for a field.
Look after them and they'll last
Knock off the mud after wet walks, let them dry naturally away from radiators, and treat the suede now and then. A little care after each outing is what turns a good pair of boots into a great investment. Pair them with the right kit — our guide to choosing an everyday backpack covers the carry side of wet-weather days.