Start with the ground under your feet

British walking is rarely a single surface. A morning on a limestone dale might mean wet grass, a slippery rock slab, a boggy patch where a path should be, and a stony track that rattles your knees on the way home. Then the weather changes its mind twice before lunch. A boot that suits all of that is a compromise, but it is a compromise worth getting right, because cold, wet feet turn a good day out into a trudge.

Before you look at price tags, think honestly about where you walk. Flat riverside paths and well-drained downland ask far less of a boot than peat moorland, Lakeland passes or a winter round of a windswept ridge. Buy for the hardest day you realistically expect, not the gentlest.

Ankle support: how much do you actually need?

Ankle support is the first thing most people think about, and it is worth separating two ideas: height and stiffness. Height protects against knocks, scree and heather, and gives a bit of stability when you are tired. Stiffness is what stops the ankle rolling on a rutted path or a tussock hidden in long grass.

• Low shoes are light and cool, and perfectly adequate for towpaths, forest tracks and gentle field paths in dry weather.
• Mid boots suit most UK walking: enough support for rough paths and a day pack, still comfortable on tarmac and lanes.
• Higher, stiffer boots come into their own on rocky ground, steep descents and when you are carrying a heavier pack or walking in winter.

Bear in mind that no boot strengthens your ankles. If you roll them often, a stiffer boot buys you time but the real fix is a lighter pack, poles on descents, and a bit of balance work.

Waterproofing, and its limits

Most fabric boots use a waterproof membrane sandwiched inside the upper, while leather boots rely more on the hide itself plus a treatment. Both work, and both fail in the same predictable ways. Water gets in over the top through your socks, through a worn-out lining, or through a fabric upper that has soaked up so much water that the membrane can no longer breathe.

That last point matters. A soggy outer is a heavy, cold outer. Keep the upper clean and re-proof it regularly with a suitable wax, cream or spray, and your boots will stay lighter and warmer as well as drier. Full-grain leather is more forgiving of abuse and easier to revive, but it is heavier and takes longer to break in.

Gaiters are not a fashion statement. On wet heather, deep mud and long grass they keep water out of your socks and stop the tops of your trousers wicking it down into your boots. Tucking waterproof trousers over the boot cuff helps too.

Breathability: the bit people forget

Every waterproof boot traps some sweat, and damp feet get cold quickly once you stop moving. If you run hot, look for a boot with fabric panels and a mesh tongue rather than a fully leather upper. It will breathe better, though it will scuff and soak through sooner.

• Wear one pair of well-fitted wool or synthetic socks rather than two thick pairs that bunch.
• Take spare socks and change them at lunch if your feet are damp — it resets the whole afternoon.
• Pull insoles out overnight so the boot can dry from the inside as well as the outside.
• Never dry boots on a radiator or beside a fire; the heat cracks leather and delaminates linings.

Grip: tread, rubber and where it lets go

Grip is where cheap boots betray you. Look for lugs around four to five millimetres deep, widely spaced enough to shed mud rather than clog. A defined heel brake helps enormously on steep, greasy descents, and a slightly rounded toe gives you purchase on rock.

Rubber compound matters as much as pattern. Softer rubber sticks to wet rock but wears faster; harder rubber lasts but slides. No tread, however aggressive, will save you on wet wooden boardwalks, polished limestone, or green algae-covered rock beside a stream. Treat those with respect and take them slowly.

Check your soles each season. Once the lugs are rounded off in the middle, you have lost most of your grip on mud — that is the moment to resole or replace, not when a hole appears.

Fit, socks and buying sensibly

Fit beats every feature on the box. Try boots on late in the day, when your feet are at their largest, and wear the socks you actually walk in. You should be able to wiggle your toes without them touching the front, and your heel should stay put when you walk uphill on the shop's ramp. A boot that slips at the heel will rub, no matter how good the membrane.

Allow a little extra length if you wear thicker socks in winter, and remember that feet swell over a long day. Buy from a shop that will let you return boots worn indoors, walk in them on carpet for an hour at home, and break them in gradually — short local walks before a big hill day. Looked after properly, a well-chosen pair will keep your feet dry through many a British summer shower, and quite a few winters besides.