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How to Wear Boots With Literally Everything in Your Wardrobe

Which boot goes with which hem.

Woman in a belted khaki trench and burgundy heeled boots walking under a black umbrella on a rainy street

Nine pairs of boots might sound excessive. It isn't. Each one does a specific job, and once you know which boot goes with which hem, getting dressed in winter gets so much easier. Here's the cheat sheet.

The workhorse

Ankle boots

These go with jeans, trousers and midis. The only rule is that your hem should either cover the top of the boot or stop well above it. That awkward gap of shin in between? Not the one. Russell & Bromley and Kurt Geiger for leather that lasts, Dune for a cheaper fix, Vagabond for chunky Scandi soles, and Hush if comfort comes first.

Skirt season

Knee-high boots

Made for midi skirts and dresses. The hem should overlap the top of the boot so no leg shows. Pop them over skinny jeans too, if you're brave enough to bring those back. Toteme is the splurge everyone wants, Sézane does lovely slouchy suede, & Other Stories sits in the middle, and M&S has wide-calf fits that actually fit.

Dark brown croc-effect knee-high boots with a kitten heel worn with a denim skirt
Croc knee-highs and denim. Works every time.
Hem over the boot, or well above it. Never the awkward bit of shin in between.

Off duty

Chunky lace-ups

These are what make a floaty summer dress work in November. Add thick tights and a big knit and you're there. Dr. Martens are the obvious ones (wear them in at home with thick socks, trust us), and Ganni if you want something a bit more fashion. Office and Schuh stock loads of brands, so they're the place to try on a few.

Having a moment

Western and slouch boots

Cowboy boots are still going strong. Wear them with straight jeans tucked in or a mini and an oversized blazer. Revolve is brilliant for these, stocking everything from Larroudé to Isabel Marant. Free People leans boho, and Zara is the place to test the trend before committing.

Woman in white wide-leg jeans and a cropped black leather jacket carrying a coffee
White jeans, black leather, boots hidden under the hem.

Big-ticket browsing

Designer boots, all in one place

For Khaite, Gianvito Rossi, The Row and the rest, Net-a-Porter, Selfridges and Mytheresa are the big three. The shoe hall at Harrods is worth a visit even if you buy nothing. Farfetch pulls from boutiques all over the world, so it's good for sizes that have sold out elsewhere.

The fit

Getting boots that actually fit

For knee-high boots, measure the widest part of your calf before you order anything online. Most brands list the calf width, and it saves a lot of returns. Duo is brilliant for this, with boots in several calf widths per size, and plenty of high street brands now do wide-fit versions too.

Try boots on with the socks or tights you'll actually wear. Thick wool socks can take up half a size. And walk around on a hard floor. If your heel lifts or your toes hit the end on a slope, they're not the ones.

The colours

Black, brown or something else?

Black is the safe first pair and goes with almost everything. Chocolate brown is softer and looks lovely with navy, cream and denim. If you already have both, try burgundy or a suede in tobacco. Suede looks richer than leather, but it needs a protector spray before the first wear and it hates salty pavements, so save it for dry days.

The care

Make them last more than one winter

Get a rubber sole fitted at the cobbler as soon as you buy a leather-soled pair. It stops you slipping and stops the soles wearing through. Wipe off salt marks with a damp cloth the same day, because they stain. Polish leather every few weeks, and stuff tall boots with newspaper or a boot shaper so they don't slump at the ankle. Reheel them before you hit the metal, not after.

The tights

What to wear underneath

With skirts and dresses, opaque black tights matched to black boots make your legs look endlessly long. With brown boots, try chocolate tights instead of black for a softer look. Ribbed or cable-knit tights are cosy and look great with chunky lace-ups. Stock up on decent ones from John Lewis, Falke or Heist. Cheap tights ladder by lunch and fall down by teatime.

The cheat sheet

Wide trousers: heeled ankle boots, hem almost touching the floor.

Straight jeans: ankle boots under, or western boots with the jeans tucked in.

Midi skirt: knee-highs, always.

Mini: chunky lace-ups or slouch boots, plus opaque tights.

Summer dress you refuse to put away: Docs and a big jumper. Obviously.

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