EVELYSS / Guides / Fashion Sense

What to Wear With Chelsea Boots (Women): Jeans, Trousers, Skirts and Six Outfits

“A Chelsea boot is the easiest boot you'll ever own, and that's exactly why people stop thinking about it. The boot isn't the problem. The hem is. Fix that one centimetre and the same pair suddenly looks expensive.”Her take

Where should your hem stop with Chelsea boots?

This is the question that makes the outfit work. A Chelsea boot has a low, sleek shaft and elastic side panels, so the top of the boot is on show unless you decide otherwise. Stand in front of a full-length mirror in the boots and check where your hem lands.

Trouble starts when fabric piles up on the boot or catches on the back tab. Choose one of three clean finishes instead.

• Just above: cropped hems ending a finger or two above the boot, showing a small gap of ankle or a matching sock.
• Just touching: straight hems that rest lightly on the top of the boot with no more than one soft fold.
• Fully over: wide or flared legs that cover the boot and fall to a few centimetres above the floor.

Which jeans work best?

Straight-leg jeans are the safest choice. Take the hem up so it just touches the boot, and if they're too long, get them altered or fold them once to the inside rather than rolling a chunky cuff. Slim jeans work best with a slim boot, and can go over the boot if they have a little stretch at the ankle.

Wide-leg and barrel jeans need a bit more thought. Wide-leg jeans should cover most of the boot and suit a chunky sole, which balances the volume. Barrel shapes taper at the hem, so they should stop above the boot to show off their curve. Skinny jeans still work, tucked in neatly, but pair them with a longer knit or coat for a more current line.

How to wear them with smart trousers

Chelsea boots are an easy swap for court shoes in cold weather, as long as the boot is sleek. Look for a slim toe, a smooth leather finish and a sole that isn't too chunky. With tailored trousers, ask for the hem to fall over the top of the boot, covering the elastic, so the leg runs in one unbroken line.

Black boots with black or charcoal trousers will look the most polished for work. Brown leather looks good with camel, cream, tweed and navy. On a wet commute, a rubber sole with a good grip won't look out of place with wool trousers and will keep you steadier on wet pavements.

Can you wear Chelsea boots with a skirt or dress?

Yes, and they're at their best with a slightly unexpected partner. Mini skirts and shorter dresses look neat and modern with black opaque tights and a black boot, because the leg reads as one long line. A chunky sole adds weight at the hem, so it pairs well with a thick knit or a tailored coat on top.

With midi and maxi skirts, look at the gap. As a rough guide, leave a clear hand's width or more of leg or tights between the hem and the boot on a midi, or let a maxi cover the top of the boot altogether. Mid-calf hems with a very chunky boot can look heavy, so try a lighter sole or a longer skirt if it feels like too much.

Black, brown or suede?

If you own just one pair, make it black leather. It works with denim, tailoring, dresses and tights, and scuffs show less on it than on paler shades. Dark brown is softer and looks lovely against navy, cream, camel, olive and blue denim. It's the better option if most of your wardrobe sits in warm colours.

Suede looks more relaxed but needs more care, so save it for dry days or protect it before the first wear. Tan and taupe suit weekend outfits, with jeans, cream knits and a wax jacket. As for socks, keep them out of sight, or let a fine wool one show deliberately above a cropped hem.

Six outfits to copy

Each of these starts with something you probably already own, so try them before buying anything new.

• Weekend: straight-leg mid-blue jeans, cream crew-neck knit, navy wool coat, dark brown boots.
• Office: charcoal wide-leg trousers over black boots, fine black roll-neck, long tailored coat.
• Evening: black satin midi skirt, thin black knit, black opaque tights, sleek black boots.
• Country pub: dark jeans, tweed jacket, ribbed knit, chunky-soled brown boots.
• Dress day: long-sleeved navy jersey dress, black opaque tights, black boots with a slim sole.
• Rainy commute: cropped black trousers, black fine-knit socks, black rubber-soled boots, belted trench coat.

Questions people ask

The takeaway

Sort the hem first: above the boot, just touching it or fully over it. Then let black handle the smart outfits, and brown and suede handle the easy ones.

Read next