The ugly-pretty shoe edit that will make everyone do a double take

Remember when wearing Crocs in public was considered a fashion crime? Or when split-toe shoes made bystanders uncomfortable? It's funny how the most divisive shoes turn into cult favourites over time. Today, anyone rocking chunky dad sneakers is considered cool. Wearing fisherman sandals is a sign that you're chic and intellectual. Ugly isn't an insult anymore. It's an aesthetic.

The ugly shoe theory is a movement in itself. It's the antidote to boring outfits. Want to spruce up a basic outfit? Add a shoe that's a little ironic. Want to add edge to your farm-core sundress? Throw on a pair of Tabi-style sneakers.

Ugly shoes are simply interesting footwear—pairs that challenge your own reservations when it comes to styling. Think chunky or super-sleek silhouettes, playful colours or nostalgic charms, funky laces or eccentric detachable accessories, either one or all of the above.

A pair of ugly shoes will add character to even the simplest white T-shirt and jeans, reminding us that great outfits often begin from the ground up. Whether you're easing into the trend or fully embracing fashion's delightfully weird side, these are the pairs worth making room for.

The brogue-inspired sneaker: CHK Stride OG

Chocolate brown sneakers might once have felt like an odd choice, especially when everyone was reaching for white trainers, but they're starting to look a lot more interesting. With celebrities like Rihanna and Simone Ashley making a case for brown suede sneakers, it's time to give the colour a second look. CHK's Stride OG in Dusk Chocolate/Birch is just the pair to start with. It combines deep brown suede with contrasting birch leather accents and a black sole. The roomy toe box gives it a brogue-like silhouette, bringing a touch of dress-shoe charm to an otherwise relaxed sneaker. Basically, it has the old-school appeal of a dress shoe without asking you to sacrifice the comfort of your favourite sneakers. Wear them with relaxed tailoring, straight-leg jeans or a floaty dress for that unexpected edge.

The conversation starter: Crocs Lego® Masterbrand Creativity Clog

Few shoes have had a redemption arc quite like Crocs. Remember when the 2006 satirical sci-fi comedy film Idiocracy joked that in the future, only the least fashionable people would wear them? 20 years later, Crocs have become a street-style favourite and one of fashion's most unexpected success stories. This Lego® x Crocs collaboration is proof of the brand's evolution, demonstrating how footwear can be playful and stylish every step of the way.

Complete with colourful, oversized Lego brick-inspired Jibbitz and brick detailing along the sole, these clogs tap into childhood nostalgia while making your feet look like their own tiny Lego universe. If you're looking for a shoe that guarantees compliments and plenty of "Where did you get those?" this is it.

The fashion editor's favourite: Melissa Possession Fisherman Sandals

The fisherman sandal is fashion's ultimate "if you know, you know" shoe, and it is bound to earn you style points in insider circles. Melissa has been championing the jelly version since the '90s, long before its return to the trend cycle. The Possession sandal brings together nostalgic Y2K charm and everyday practicality through its glitter-flecked translucent finish and signature caged upper. 

It also happens to be one of those rare shoes that are completely androgynous, embraced by women, men, and non-binary style enthusiasts alike. Need more proof? Just ask The Dude from The Big Lebowski. Turns out, he was onto something.

The nostalgia trip: Puma x Superkicks Palermo Stained Sneakers

Puma's Palermo has enjoyed a major revival in recent years, becoming one of the brand's most coveted retro sneakers thanks to its terrace-inspired silhouette and vintage appeal. This limited-edition collaboration with Superkicks gives the classic an unmistakably Indian spin.

Inspired by the purple stains left behind after eating ripe jamuns, the Plum Wine colourway celebrates imperfect childhood memories through rich suede, distressed detailing, and a beautifully worn-in finish. It's a unique piece to own and is definitely a collector's item. This sneaker reminds you to embrace a little mess, live a little more freely, and wear every scuff, stain, and story with pride.

The artisanal pick: Fizzy Goblet Madras Calling Mules

Fizzy Goblet has built its reputation on reimagining traditional Indian craftsmanship through a contemporary lens, and these Madras Calling mules are no exception. Woven in vibrant Madras checks and finished with playful leather tassels, each pair celebrates artisanal detail while the slip-on silhouette makes it an easy everyday choice. 

The riot of colours means they'll instantly lift even the simplest outfit. And the best part? You don't have to worry about matching them to the rest of your wardrobe.

The homegrown hero: Comet Aeres 

Comet is shaping up to be one of India's most exciting sneaker brands, thanks to its playful approach to design and its knack for turning everyday footwear into conversation starters. From its mind-blowing limited-edition drops like the Maachis sneaker, inspired by vintage Indian matchboxes and designed to literally light a match, to its Uno sneakers modelled after the world's favourite card game, the label has built a reputation for creating shoes that ignite originality. 

The Aeres Picnic Red continues that spirit with its retro gingham print, bold colour blocking, and detachable tongue. It's a refreshing departure from a sneaker culture dominated by celebrity collaborations and familiar logos, proving that personality is the best flex.

The sneaker boot: Converse Chuck 70 De Luxe Pointed Platform Woven Leather

Converse might be best known for its canvas classics, but this woven leather silhouette proves the brand can do directional design just as well. The glossy woven upper, pointed toe, and monochrome finish give the shoe a witchy appeal that works just as well in the office as it does after dark. 

Think of it as the perfect alternative for anyone who loves the look of boots but prefers the comfort of sneakers. It's also surprisingly versatile, pairing effortlessly with sharp tailoring, vintage-inspired midi skirts, and mini dresses alike. The shoe is a reminder that sometimes the boldest statement isn't made with colour—it's made with silhouette.

The court star: Nivia Starliner Basketball Shoe

Basketball shoes aren't just meant for the sport. They've long since made the leap off the court and onto the streets, and Nivia's Starliner makes a convincing case for why. 

Built with performance in mind, it packs breathable mesh, responsive cushioning, and a supportive frame, but it's the striking botanical green upper and contrasting yellow sole that steal the show. Even if your closest encounter with basketball is watching courtside style on Instagram, this pair delivers serious visual impact.

The split-toe statement: Nike Air Rift

If Maison Margiela's Tabis feel a little too intimidating, meet their sportier cousin: the Nike Air Rift. Originally inspired by barefoot running, the Air Rift has developed a cult following thanks to its unmistakable split-toe design. This version softens the silhouette with scalloped trims and glossy polka dots, striking a balance between athletic performance and everyday style.

And if polka dots aren't your thing, the Air Rift also comes in everything from croc-embossed finishes to lace-trimmed versions. It's one of those unconventional shoes that only gets better the longer you wear it.

The platform obsession: Cai Canvas Bloom Thong Platform

Chunky flip-flops are one of fashion's favourite summer silhouettes, and Cai's Canvas Bloom Platform embraces the trend with plenty of personality. Floral jacquard straps, a statement buckle, and a generous platform sole make these shoes elegant and elevated, playful and bold, all at once.

Surprisingly versatile, they're just as happy paired with floaty dresses as they are with oversized streetwear styles, proving that elevated comfort is very much having a moment.

The retro revival: Onitsuka Tiger Rotemit

If Kill Bill introduced a generation to Onitsuka Tiger, the brand has kept sneaker lovers hooked with its signature blend of Japanese craftsmanship, comfort-first design, and retro silhouettes that never go out of style. The Rotemit builds on that legacy, reimagining one of the label's 1980s volleyball shoes for today. 

This Birch/Deep Mars colourway, with its cream canvas base, soft pink and sage green suede panels, signature brown Tiger stripes, and caramel platform sole, looks like it stepped straight out of an '80s coming-of-age film. Prefer something more understated? The Rotemit also comes in versatile colourways like Black/Graphite Grey, Cream/Olive Green, and White/Blue, so there's a pair for every kind of sneaker lover.

These pairs won't be everyone's cup of tea, and that's what makes them so much fun. Unexpected, conversation-starting, and just unconventional enough to make people look twice, they have a way of growing on you. Don't be surprised when the very pair someone laughed at today ends up on their wishlist tomorrow.

Lead image: Featured brands

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