Much like a crisp poplin shirt or cotton-rich tee, Chelsea boots have been a quiet marker in the fashion industry since the 1800s, although it rose to prominence in 1950s Britain, hence its moniker. It was there it was donned by tastemakers and became a voguish shoe. Throughout the years Chelsea boots have been reinvented myriad times (albeit subtly), whilst retaining specific characteristics, such as the distinctive elasticated panels, ankle length and more often than not, an ankle tab for ease of wear.
Chelsea boots are now a significant piece for men and women, particularly during the cold seasons. Come autumn, Chelsea boots become a staple piece in a footwear capsule and it's fair to say we've now reached the point where people are reaching for hardened footwear options. Not only are flat soled boots a uniform piece , it also boasts a practical quality as we usher towards wet days when impermeable footwear is much appreciate (and often a necessity). Although the Chelsea boot is typically characterised by a rounded toe and lug sole, the evolution of the style has paved way for many iterations including almond, pointed and squared-off shaped toes, with some styles even bearing an added heel height. Due to this, Chelsea boots have become a staple coveted and acquired by many, regardless of individual style.
From lug sole versions to block heels, I've rounded up some of the best Chelsea boots I've seen across the high street and designer brands this season. Keep on reading to discover the styles that have my caught my (discerning) eye this season.
Shop The Best Chelsea Boots:
Hush's Aaliyah boot comprises an elongated shaft and grained leather, meaning it'll be more forgiving with marks and scuffs.
For something a bit more directional, why not opt for a square-toe iteration.
This style has an ever so slight androgynous feel to it as the sole bears a resemblance to men's brogues.
This chunkier iteration offers an almond shaped toe and slightly raised platform. It's also crafted from chrome free leather, which is always something to appreciate on the high street.
Chelsea boots are well-loved by French women during the transitional and winter seasons. Designer Isabel Marant have created the ultimate chic, fuss-free shoe. It's undeniable classic and subdued.
It's possible to invest in good quality pieces on the high street too. Simply look-out for shaping and fabrication. These Massimo Dutti boots would be hard to pick out of a designer line-up.
Look closely for the cushioned sole. It'll offer you added bounce in your step.
British designer Penelope Chilvers is a quiet name in the industry but those familiar with it will know it's best associated with quality craftsmanship.
Reformation crafted the ultimate in-between boot that is suitable for myriad occasions. Practical enough for country walks, yet it's also a style you can team with dresses.
Dear Frances have cornered the market when it comes to sophisticated and mid-priced footwear and I can't recommend the quality enough.
I own a Vagabond boots and I can guarantee the quality is second to none, especially at its more attainable price point.
R.M Williams created a western-inspired Chelsea, due to the upturned toe.
This pointed toe and lower shaft is a great style to acquire if you tend to wear jeans often. It's particularly great for slipping on with straight-leg jeans!
You may be familiar with Toms for its infamous espadrille style, however they also boast capsule footwear collections to go alongside. The Rowan boot is the latest boot offering, and not only is it a universal style, it's also water resistant!
Handcrafted in Northamptonshire by Solovair, these boots are made with attention to detail in accordance with a 130-year old technique. After forming the signature Chelsea shape, the body is then adhered onto a goodyear-welted sole, offering a casual element suitable for weather extremities.
I wear dresses right through to winter and I love the pairing with heeled Chelsea boots. It instantly smartens an outfit.
A concave shape courtesy of Me + Em, crafted from LWG-Approved Full-Grain Leather.
You can't mention Chelsea boots without the mention of Italian atelier, Tod's. If you're looking to invest in timeless designs crafted from luxurious fabrications, look no further.
There are many design features to applaud, from the lacquered gloss to the slender silhouette (not to mention Aeyde's mastery in elevated design and high quality fabrications). These boots are a contender for those who prefer form-fitting footwear.
Now, this is what you call a smart Chelsea boot. What differentiates it from other styles is the polished leather, tonal stitch and hardened sole (as opposed to gripped). It's a style of boot you can seamlessly transcend from weekend wear to an office dress code.
Essēn's arsenal consists of mindfully produced leather goods. Although their designs are usually classic, the contrast stitching loans this boot a directional feel.
Up Next, Just In: The Formula for a Truly Easy Winter Capsule Wardrobe
-
Trust Me: I've Looked—These Are the Chicest Knee-High Boots on the High StreetFrom kitten to stiletto.
-
Gwyneth Paltrow Wore the Chic Boot Trend That Goes Best With Slim-Leg TrousersI'm digging out my slim-fit trousers for this.
-
I Can't Face Wearing Heels—5 Flat-Boot Looks That Are Just As PolishedThe chunkier, the better.
-
Sienna Miller’s Boots Could Be Called "Dated", But Her Jeans Are So 2025An outfit she wore whilst hanging out with J.Law!
-
Hold the Jeans—Celebrities Have Confirmed They're Be Wearing Leggings and Boots All Winter LongI'll be doing the same.
-
European Women Rely on This Elegant Coat Trend to Look Polished in Winter—18 of the Best for Every BudgetA modern classic.
-
Jennifer Lopez Just Wore the Boot Trend That Londoners Are Styling With Jeans This WinterNow I want a pair.
-
6 Winter Outfits That Are Guaranteed to Make You Look RichFrom a designer-loving editor.
