How To Style Chelsea Boots Like The Stars In 2025

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There have been several hot, celebrity-backed fashion trends dominating 2025, with Hollywood's brightest stars providing solid style inspiration for en vogue pieces throughout the year. But one that we've been happily embracing is the resurgence of the ankle boot — particularly Chelsea boots. Though Chelsea boots extend beyond these fashion cycles as versatile footwear you need in your closet, stars have similarly been bringing some moodboard-worthy 'fits featuring the shoes that translate into much-needed styling tips. Ranging from edgy, plaid-heavy ensembles to cold weather-ready looks, they've provided a little bit of something for almost every aesthetic.

If you're unfamiliar, Chelsea boots are a style of footwear known for their ankle height and elastic side panel, with many variations featuring pull-on loops. While the footwear can be traced back to the early 1800s, the shoe style experienced major popularity in the 1960s, being trendy in London's Chelsea neighborhood and worn by celebs like The Beatles. Since then, the ankle boots have undergone plenty of innovations, including being designed with varying textiles, heel heights, and detailing. This year, rubbery and leather-heavy Chelsea boots have maintained popularity, with celebs proving just how versatile the unisex footwear truly is.

Daisy Edgar-Jones demonstrated how Chelsea boots can add an utilitarian spin to feminine pieces, pairing a beige, bias-cut dress from Anemos Gisele with a pair of elastic-paneled rainboots from Hunter. She accessorized with a pair of plain socks, oval sunglasses, and a raffia handbag, looking casually cool when pictured at the Glastonbury Festival in June 2025. While Chelsea boots wouldn't be our first thought when styling the elegantly playful dress, Edgar-Jones' choice of footwear definitely gives the ensemble a more grounded and casual vibe that feels perfect for her day in the sand.

While there is a specific way everyone was wearing plaid for fall 2025, Jisoo of Blackpink went for a classic punk-inspired look by styling a chunky pair of Alexander McQueen's Chelsea boots with an asymmetric tartan dress from the designer brand. The K-pop idol styled the edgy combo with layered necklaces and a casual ponytail, sporting the outfit during Blackpink's Deadline World Tour. The resulting look shows that Chelsea boots can cultivate a playfully edgy vibe when paired with the right pieces, with similar items like a classic red flannel or leather jacket channeling the same energy when worn with the footwear.

Bella Ramsey leaned into the unisex vibes of Chelsea boots at the UK premiere of "The Last of Us" Season 2, sporting the same Alexander McQueen pair as Jisoo. The England-native styled the chunky ankle boots with a floral tapestry jacket and tailored black slacks, completing the look with middle-parted hair styled in loose waves. The outfit plays with gender by combining flowery motifs and crystal accents with tailored menswear, but there's also a contrast between the antique energy of the tapestry and the timeless vibe of the ankle-height footwear. In this way, Ramsey's red carpet look proves that Chelsea boots can bring a contemporary touch to vintage pieces when styled correctly.

Gemma Chan provided even more Chelsea boot inspiration when attending the Glastonbury Festival in June, combining practicality with style in her concert-ready look. The "Let Them All Talk" actor paired leather ankle boots from Barbour with a two-piece set, accessorizing with an oversized flannel, large sunglasses, and a variety of bracelets. The matching khaki pieces play into the utilitarian feel of the boots while doubling as solid picks for a festival day, but Chan kept things stylish and casual with her breezy accessories. The overall ensemble is a reminder that pieces don't have to be boring just because they're practical, especially when it comes to Chelsea boots.

Elizabeth Olsen added to the list of fashionable celebrity outerwear looks when the "WandaVision" actor was pictured in New York City back in March. She wore a long, brown coat featuring a wide lapel over a beige, v-neck cardigan and a white mock-neck shirt. Though her footwear isn't completely visible under dark-wash jeans, the star clearly wore chunky, rubber-soled shoes reminiscent of Chelsea boots from brands like Free People. Olsen's cold weather-ready outfit demonstrates how combining the right pieces, like a statement jacket with timeless boots, can boost a minimalist approach to fashion to chic status. Build your own version of the look with AMPOSH Women's High-Rise Straight Leg Jeans In Faded Charcoal and Utcoco Women's Faux Suede Long Trench.

While Margot Robbie's simple airport 'fit provides great inspiration for those looking to travel in style, the casual ensemble doubles as an example of how to wear Chelsea boots for an effortless cool-girl vibe. The Aussie actor paired an army green button-up with straight-leg jeans, punctuating the combo with a black crop top, leather bag, and ankle boots from Celine. Though pretty simple, the outfit manages to balance utilitarian-inspired pieces with casual staples in a way that feels very effortless. So, when in doubt, take inspiration from Margot Robbie and pair your Chelsea boots with similarly timeless, but casual staples. 

Next, Yeji of the K-pop girl group ITZY paired Chelsea boots with a preppy aesthetic for a Tommy Hilfiger photocall, wearing a knitted, button-up cardigan with a corduroy miniskirt to the October event. The two, brown-toned pieces create a cozy academia vibe that feels perfect for autumn, while the classic ankle boots add a contrasting element with their straightforward look and black color. The combination has the potential to feel disjointed, but the resulting outfit ultimately feels like a slightly more grounded iteration of playful preppiness, demonstrating how well the shoes can slot into different styles and aesthetics. Create your own with a Simplee Women's Cardigan and a Fengbay Corduroy Skirt.

Maddie Ziegler rounds out our list of celebrity looks with an outfit from November 2024, with the styling inspo remaining relevant well into 2025. The former "Dance Moms" star used Chelsea boots to add color to a monochrome outfit, sporting a bomber-style leather jacket and cuffed, dark-wash jeans with a crocodile-patterned pair of red ankle boots. The unexpected hue adds an extra flair to the chic outfit, with Ziegler looking sleek and mysterious as a result. So, while Chelsea boots have been a grounding element of several celeb looks, they can also add a little spice.