Once upon a time, in a fashion world that existed not too long ago, the Margiela Tabi was considered the most outlandish style of shoe a person could wear. Fast-forward to today, when even Kylie Jenner wears them on a date via Citibike, it takes more than a split toe to scare off non-fashion folk. We have jelly shoes fit for Polly Pocket, orthopaedic sports sneakers with velcro straps, neoprene and a high arch for support, "toe cleavage" and complete exposure therapy courtesy of Saint Laurent’s men’s PVC brogues and Chanel’s "sole-less" sandals. Fashion commentator Mandy Lee said it best when she declared us in a "freaky shoe era". No style, shape or hybrid is out of bounds, because fashion’s latest fetish doesn’t discriminate; it democratises.
Whilst we may be heading into autumn, let’s begin by paying summer’s most eccentric syles theirs dues. A while ago I waxed lyrical on the rise of "princess shoes", footwear that panders to our inner child who wanted to dress up in Cinderella’s glass slippers or Marie Antoinette’s mules. Jelly shoes might have made their return in 2025, but Chloe’s Chemena Kamali pushed the boundaries of shoe design fit for our seven-year-old selves by dropping her PVC jelly mules. Pastel and peep-toed, they echo the sentiment of Aqua’s lyrics of pure poetry: “Life in plastic, it’s fantastic".
But if plastic isn’t your thing, fear not, Matthieu Blazy’s Chanel Cruise collection has a sandal for you. Designed in black leather with long laces to be tied around the ankle, they look relatively traditional until you realise they have no sole. Half the shoe, but not half the price.
Back in June, when the menswear spring/summer 2027 shows were presented, it was clear they too got the message. Lace-up ballet flats at Dries van Noten, derby jazz shoes and barely there sandals at Celine and—wait for it—transparent pointed PVC brogues and boots at Saint Laurent. Woof! Some of these styles aren't yet available, but they still set the tone for the season ahead. And as we all declared an end to quiet luxury and the rebirth of maximalism, our tippy-toes got the bedazzled treatment. A harem of toe rings, charm anklets and embellished flip-flops filled our Instagram feeds, and this was just the beginning. 2026 has been declared the year of whimsy more than once, and what's more whimsical than Chanel’s haute couture show being inspired by fairytales such as Jack and the Beanstalk? With golden eggs, ornate butterflies and decorated legumes for heels, the collection made JW Anderson’s frog clogs of 2023 or BHIVE’s duck flippers feel like child’s play.
Princess mules or butterfly-and-beanstalk heels; what’s clear is that "freaky" no longer simply equates to "ugly". In fact, autumn/winter 2026's most outlandish styles are prettier than ever. There are Tory Burch's embellished pumps, Dior’s waterlily sandals and Prada’s feathered and beaded lime green lace-up boots, and the level of intricacy and craftsmanship proves that there’s method in the madness.
Dior’s director of footwear design, Nina Christen, is responsible for the house’s brilliantly bold designs under Anderson’s leadership. If one were speaking in musical terms, the autumn/winter couture 2026 footwear collection was a seminal album with a no-skip tracklist. Bows, beads, feathers and florals upon taffeta silks and pastel mesh: every inch of shoe was a smorgasbord of fabulously fun, feminine decoration.
But what else can we expect from shoes in A/W 26? Another Mandy Lee prediction that came to fruition (because honestly, when does she miss?) was the presence of hair. Simone Rocha, Dries van Noten, Erdem, Marni and Miu Miu are offering everything from ballet flats to boots with shearling exteriors and long-haired toes that give zero f**ks whether it rains or pours, because they’re not made with practicality in mind.
Looking at the runways, if you were thinking some styles felt somewhat familiar, you’d be correct. The Valentino Garavani Rockstud returns with a new 'do courtesy of Alessandro Michele, and Gucci’s monogrammed foldable-heel courts might just be tempting us with the return of logomania (yes, it's due a comeback, but you heard it here first). Others are reminiscent of a bygone era much further back than the 2000s or 2010s, however. We all know this time of year is the season of the witch, and with Practical Magic 2’s release, it couldn’t be a more welcome time for Victorian footwear to come to the fore. Lace-up boots might have been trending since last winter, but it’s the elasticated Khaite courts with their turned-up toe that have a distinctly spooky feel.
As such, whether you’re looking for shoes fit for a princess, a witch or to allude to the fairytale-loving inner child within us all, I think Nile Rogers said it best: "Le freak, c’est chic"!
Shop Freaky Footwear for Autumn/Winter 2026
