Well heeled: The Best Chelsea Boots and How to Wear Them

Whether you choose a pair that's chunky, flat, or heeled, the best Chelsea boots are those that offer both comfort and versatility. Our new collection has a range of timeless designs to see you through the seasons, including those with Insolia technology to balance the weight in your foot and support your posture. When considering the best women's Chelsea boots for you, take into account how often you'll wear them, what occasions you'll wear them for and your wardrobe's colour palette to ensure you get the most wear out of them.

Key footwear styles for autumn/winter '25 include premium Chelsea boots made from leather and suede which offer great cost-per-wear value, thanks to the hardwearing nature of the materials. We have durable designs by M&S Collection and Autograph, as well as covetable styles from your favourite footwear brands, including Finery London, LK Bennett and Dune London.

Chelsea boots were made for casual dressing. Thanks to the stretchy sides, the slip-on design lends itself to everything from everyday wear, to walks in the countryside and even horseriding. For casual days in the city, team a black chunky-soled pair with a grey wool overcoat, a sweater and straight-leg jeans for a contemporary Chelsea boots outfit.

In the 1960s, the Chelsea boot became synonymous with the style and music scene of London's King's Road. The Beatles gave Chelsea boots a smart-casual spin by having bespoke pairs made with a higher heel, ideal for teaming with the era's sharp Italian suiting. For modern women's Chelsea boots outfit ideas, step out in a slinky knitted dress or a tailored trouser suit. A pair of dark wash jeans with a going-out top is another idea of how to wear Chelsea boots out to dinner or drinks.

If you're eyeing your Chelsea boots and wondering if you can wear them out-out, it's a 'yes' from us. Look for styles with heels or a flatform sole to elevate your look. When considering what to wear with Chelsea boots for a dressier occasion, bear in mind that luxurious details, draped fabrics and sophisticated cuts will smarten Chelsea boots, whereas mini skirts, frayed jeans or ditsy florals will keep the outfit firmly in daywear territory.

Jeans and Chelsea boots are a match made in heaven. If your go-to jeans are skinny-fit or slim-leg, you'll want a pair of streamlined Chelsea boots to match. Balance proportions with a narrow toe and a flat heel. When you're pondering what jeans to wear with Chelsea boots, we recommend sticking to the cut you're most comfortable with and building an outfit around it: add volume with loose blouses, chunky knitwear and an oversized coat.

Wide or straight-leg jeans are a flattering trousers option to wear with women's Chelsea boots – the looser cut complements chunkier footwear styles including flatform boots. A denim dress or skirt is another idea for when you want to branch out from jeans: keep things cool with a cleated-sole style and ribbed ankle socks.

Our top tip for how to wear women's Chelsea boots? Keep them in tip-top condition by getting soles and heels repaired as soon as you notice them wearing down. Stock up on affordable yet effective shoe care products, such as a weatherproofing spray and a suede brush, to protect your new boots from the elements. After all, take care of your shoes and your shoes will take care of you...

Black is the quintessential colour for Chelsea boots, pairing seamlessly with everything from blue jeans to printed midaxi dresses. If you're considering a monochrome palette, stick to simple cream tops styled with grey jeans to accentuate a pair of eye-catching black Chelsea boots. Black Chelsea boots outfits don't need overthinking; their versatility means you really can't go wrong.

If you're keen to try tan leather boots, consider teaming them with cream or black jeans to create a striking contrast. A pair of glossy brown Chelsea boots, like this leather pair by Jones Bootmaker, will become the cornerstone of your year-round wardrobe, while TOMS' cosy borg-lined suede Chelsea boots get our vote for autumn/winter '25. If you're standing in front of your wardrobe perplexed by what what to wear with brown chelsea boots, combine seasonal tones: think burnt orange, forest green and steely grey for a foolproof autumnal palette.