The Freakiest Shoes on the Market This Season

These are the shoes you throw on when you don't want to stay in one lane. The ballet inspired sneakers are both delicate and defiant. Designed by Brooklyn-based Double Standard, a female-run fashion house that came from humble beginnings on Depop, these shoes can be worn anywhere: work, drinks, even a treadmill.

It's cool to have your toes out…sort of. If you have the urge to show off your piggies, but are afraid to get too cold, Sandy Liang’s Paw Mary Janes might be the shoe for you. Straying from the typical rounded toe of a mary jane, the Paw opts for a molded toe design instead, which evokes the idea of animal paws (think kittens, puppies and bears). These are definitely on the freakier end of the freaky shoe spectrum, but devoted fans of Sandy Liang are sure to be wearing them anyway.

Designer brands are getting freaky too. Saint Laurent is taking your toes to new lengths with this ultra pointed-tow stiletto. In a recent video unboxing her new pair of Amalia’s influencer Christina Kirkman (@christinakirkman), who is not afraid to do flips and headstands in her heels, addressed haters who said her new shoes were ugly. “I love them because they are so wacky and weird,” said Kirkman. Although there were many people that disagreed in the comments, many including several well-known influencers backed Kirkman up, sharing their love for the freaky shoe.

Have you always wanted to wear balloon animals on your feet? Look no further than the Sara Mule from JW Pei. The vegan leather heel comes in 15 colors and is sure to make your whimsical balloon animal dreams come true.

Looking for a little furry friend to wear on your feet? Frēda Salvador is giving you the chance. Cut in the best-selling silhouette of their Jada flat, the pony hair version (which is not actually made from a tiny horse just fyi) gives the classic style a much needed upgrade for winter 2025. Everything from Frēda Salvador is super comfy, their loafers are my go-tos, so not only will you look extra cool, but you’ll be able to walk miles in these, too.

Furry, flat, and casual, these mules by Sadi might make you think of flippers, but they may just be the key to drawing attention to your toes. The silhouette may seem intimidating at first, but paired with an oversized trouser they can bring some casual vibes to a more refined look.

The Pierre flats by Flabelus make it look like hundreds of butterflies are resting on your feet when you walk, and honestly they feel like it too. The base of the shoe is a cotton velvet and sewn onto a recycled rubber sole using Spanish espadrille methods. These flats can upgrade a simple dress and take the outfit from not to hot.

Hey, eyes up here! It’s easy to get caught staring when you see someone wearing any pair of shoes from Tory Burch’s “Pierce” collection. The silhouettes feature high heel, flat and a special inverted-heel design that's become synonymous with the brand. The namesake piercing details automatically elevate the sleek shoes no matter what style you choose. 

We all know about a green thumb, but what about a silver toe? Ballet flats are one of the most in demand styles of the season, but with just a few minor adjustments they can be transformed from comfy and refined to something special. Take the Céleste flat from Manière De Voir, one of my favorite designers for affordable, unexpected fashion. By adding a silver detail right above the big toe, the brand was able to give the style a modern twist that's just a little bit freakier.

Without having to do much, tall, black, leather boots have always been a little freaky. With a detachable, leather strap, the Hillstar boot from Bared Footwear can take you from edgy to preppy in seconds. Like all of Bared’s shoes, the Hillstar is going to be one of the comfiest things you've ever put on your feet, with a biomechanical footbed that contours to your arch and a complimentary fit kit included with every pair.