Luxury footwear is undergoing somewhat of a revival. After years of sneakers and loafers dominating the shoe trends – that is to say, practical and solid styles, for the most part – fun and whimsical designs have been creeping back into the spotlight. Heels and dress shoes have had a refocus by luxury brands seeking to expand their offerings and capitalise on the explosion of interest in vintage designs.
Jonathan Anderson has led the charge for unconventional, conversation-sparking designs at Loewe (where he was creative director until last year) with styles featuring balloons, makeup brushes, and even the custom tennis ball heels he created for Zendaya for the Challengers press tour. Now, as creative director at Christian Dior, he’s bringing his signature playfulness to the iconic maison. Alongside Nina Christen (the design director of shoes at Dior), his Autumn Winter 2026 debut featured standout heels designed to look like you were walking on lily pads, with sculpted flowers blooming right out of your toes. They’ve followed it up with their recent Autumn 2026/2027 Haute Couture show with fully embellished pumps featuring beads, charms, and feathers, as well as 3D floral appliques, continuing the flower theme.
Over at Chanel, Matthieu Blazy has been setting wish lists on fire with his array of quirky takes on Chanel’s greatest hits. In the Spring Summer 2026 Haute Couture show, he featured the iconic cap-toe reimagined with delightful mushroom shaped heels, one replete with a bird perched fancifully upon the caps. His Cruise 2027 show made a bold footwear statement, in sending a shoe down the runway that was hardly a shoe at all. The barely-there sandal, consisting of thin straps wrapped around the ankles and a small heel only, leaving the sole of the foot completely unprotected, was worn on the red carpet by Margaret Qualley, sparking conversation about whether it constituted footwear at all. No matter where one may come down on it, one cannot deny that it has become a moment that people are talking about – and that may just be the entire point. The not quite barefoot, not quite sandal, is a continuation of the Chanel two-tone code, interrogated and inverted further than ever before by Blazy.
The quirky shoe has even hit men’s luxury footwear, with Saint Laurent bringing out one of the year’s most divisive silhouettes in their men’s Spring Summer 2027 show: a see-through dress shoe. The subversive design once again raises questions about what defines a dress shoe, and how it fits with a traditional suit ensemble. The conversation ignited around the design perhaps was ultimately the intended result.
Even before the latest slew of fanciful designs, the quirky shoe movement had gained serious viral momentum through styles such as the Tabi, the iconic split-toe shoe from Maison Margiela. Never before has a previously underground, “if you know you know” design broken through into the mainstream so decisively. Vintage designs have also undoubtedly helped fuel interest in the luxury footwear category, with Chanel, Gucci, and Prada all in the mix of fashion’s most wanted. One need only spend a short amount of time on Instagram to see the proliferation of online boutiques curating specific vintage drops and collections for their dedicated clientele.
The mantra currently being pushed within fashion is to embrace individuality. Vintage footwear does this by offering exclusivity and rarity. The new guard of luxury footwear is simply following along and reveling in the thrill of breaking the old rules of fashion, experimenting with style, and celebrating confidence. So have a look at the bold designs out there and perhaps choose a shoe less travelled and enjoy it, one bold step at a time.
By Sisi Levinson, Luxury Specialist
Top Image: Margaret Qualley wearing a pair of Chanel barefoot sandals / Alamy
October 2026