Some footwear trends have a way of weaving in and back out of the fashion zeitgeist. Take Mary Janes, for example: The once prim-and-proper option has shifted from being something your mom made you wear in the early aughts to an omnipresent staple in wardrobes of It girls like Hailey Bieber and Zoë Kravitz. Then there’s slingback pumps, which first hit the scene in the mid-20th century as a pin-up girl go-to, but have since undergone an edgy downtown transformation at the hands of the industry’s most notable designers — ahem, Gucci and Prada. But Chelsea boots? They’ve always felt right for the moment, making countless outfits better throughout their centuries-long existence. That’s right, centuries.
The origin of the utilitarian pull-on shoes dates back to the 1800s, when it was originally created for Queen Victoria herself. However, decades later in the affluent area of Chelsea, London (where the name comes from) it became heavily tied to the iconic King’s Road fashion scene. British rock-and-rollers like The Beatles and The Rolling Stones adopted the boots into their everyday wardrobe; in turn, it became a staple of the mod look. Since, the silhouette has remained a focal point for the British set: Just look at Kate Middleton, who frequently leans on her favorite pairs for making more casual royal appearances.
The Princess of Wales’ go-to outfit formula of fitted jeans and a timeless jacket is always a reliable way to wear Chelsea boots, of course. But the footwear lends itself to plenty of other combinations. Consider wearing yours with modern separates like leather pants, a statement mini dress, or even a sweater set. With the right styling, you can make the classic design feel totally new, whether you lean more toward a Sofia Richie Grainge-inspired easy luxury aesthetic or a grunge-y riot girl vibe à la Olivia Rodrigo.
Keep scrolling for fresh inspiration on styling Chelsea boots, straight from a few curated feeds of TZR’s favorite digital creators.
With Contrasting Fabrics
While a black Chelsea boot is certainly a staple worth investing in, make sure there’s room in your closet for a lighter pair — it’ll completely expand your outfit possibilities. They’ll go wonderfully with blue jeans, of course, but we particularly love the way the Sorel style above looks with shades from the same color family, like white and beige tones.
With A Sleek Shirtdress
If you don’t already have an elegant shirtdress in regular rotation, take this as your sign to change that immediately — it’s a classic. The beauty of the style is that while it feels so polished with fancy flats or heels, sturdy Chelsea boots make it edgy and cool (and so easy to throw on in a rush). Take cues from the outfit above and add in a furry handbag from Telfar’s collab with UGG and a bit of bling on your ears because, hey, it is holiday party season after all.
With A Flouncy Midi
Floaty dresses are essential in the warmer weather, but you can keep them in rotation much longer with a striking Chelsea boot (and, perhaps, a pair of tights). To take the outfit above up a notch, try adding in a cozy cropped jacket — baby blue would be the perfect color choice — and a sweet hair bow.
With A Matching Knit Set
On days when you’d rather just wear a sweat set, but your social calendar requires something more elevated, combine pull-on booties with a sweater and skirt co-ord. For peak coziness, pick separates in oatmeal or grey.
With A Graphic Print
If you just can’t with teetering heels, a sleek set of burgundy Chelsea boots feels surprisingly elevated at night — particularly when mixed with a graphic print dress and statement trench. Opt for a chic bucket bag as your carry-all for the evening and get ready for the compliments to start flooding in.