Men's Winter Boots: Four Shapes Worth Buying, and How to Wear Them

Men's boots come in roughly a hundred names and about four actual shapes. Once you know which shape you're after, the rest is just colour and price. Below is each one and what I'd wear it with.

The short version: a Chelsea if you want one pair for everything, a chukka if you mostly wear jeans, a lace-up leather boot if you want something tougher, and a hiker if your winter involves actual mud. FashionBeans has hiking boots and chunkier soles on its autumn/winter trend list this year, so the last two are having a moment. None of these four is going anywhere, though.

1. Chelsea boots

Elastic sides, no laces, pulls on in two seconds. The Chelsea is the most adaptable boot there is: a sleek leather pair works with tailoring, and a pair with a chunky cleated sole looks right with jeans and a parka. If you only buy one pair this winter, it should probably be this. Black is smarter. Dark brown is easier with denim.

2. Chukka and desert boots

Ankle height, two or three eyelets, usually suede, often on a crepe or gum sole. A chukka sits halfway between a shoe and a boot, which is why it suits people who don't think of themselves as boot people. It goes with jeans, chinos and cords without trying too hard. The catch is suede and British rain, so spray them before the first wear and keep a leather pair for wet days.

3. Lace-up leather boots

Higher up the ankle, more eyelets, a thicker sole. This is the workwear boot, and it's the one to buy if you want something that looks better the more battered it gets. Brown leather with straight-leg jeans and a chore jacket or a heavy knit is the classic way in. Black lace-ups lean tougher and go well with dark denim and a black coat.

4. Hiking boots

Padded collar, chunky tread, often a mix of suede and fabric. Hiking boots were made for hills, but they've moved into everyday wear, and they make sense in a British winter that's mostly wet pavements. The way to keep them from looking like you're off up Pen y Fan is to wear them with normal clothes: straight jeans, a wool coat, a plain jumper. Let the boot be the one practical thing in the outfit.

What to wear with men's boots

Most boot outfits go wrong at the hem. Skinny jeans bunch on top of a boot, and very wide trousers swallow it. Straight-leg jeans that just touch the top of the boot, or turn up once, are the safest bet with all four shapes. And thick socks matter more than people think, especially in a boot with a bit of room in it.

Sizes in the popular colours go first once the cold sets in, and prices move. If you've found the shape you want, buy it now.