‘Birkenstocks walked so five-finger shoes could run': Our ranking of the ugliest shoes

Telegraph

13 hours ago

When it comes to footwear, it's possible that 'ugly' should no longer be considered an insult. In fact, in plenty of fashion circles, it seems to be the case of the more conventionally unattractive the shoe, the better.
It's been a mixed summer for classics in the ugly-chic shoe department. German brand Birkenstock has defied profit expectations and noted a 16 per cent increase in sales, reportedly aided by the enduring popularity of the brand's 'Boston' suede leather clog, which comes in various muted shades.
Meanwhile Crocs suffered a 30 per cent slump in shares in early August after revenue was predicted to decline. It's a far cry from the halcyon days of Covid lockdowns, when the rubber clog company's revenue climbed 64 per cent in the first quarter of 2021 to reach a record-breaking £331m.
There's a chance, in a world where once-divisive sheer flats, grown-up jelly shoes, fisherman sandals and hybrid 'sneakerina' styles are de rigueur, Crocs simply haven't maintained their former shock factor. These days, Merrell, Teva, Sorel, Salomon and any other brand a British dad might have worn abroad in the Nineties have deftly transitioned from source of embarrassment to source of inspiration. Ditto podiatrist-approved names like Scholl and FitFlop.
At Copenhagen Fashion Week, lace-up ghillies inspired by Irish and Scottish dancing shoes were a frequent sight on the front row. Then there's the most polarising style of all – Vibram's FiveFingers, the toe-separating fitness shoe that's fast becoming a fashion flex.
'Birkenstocks walked so five-finger shoes could run, except now they're more likely to be traversing the natural wine bars and coffee shops of Hackney than the foothills of the Pennines,' says Joy Montgomery, British Vogue's shopping editor.
It's the latest in a long line of unexpected footwear trends, which Montgomery reasons are an offbeat antidote to increasingly homogenised style. 'In the face of social media's AI-generated perfectionism, it seems as though designers – and subsequently, fashion-savvy Gen-Zs – have been trying to out-ugly each other with their footwear choices,' she says.
'Every season has seen another orthopaedic shoe silhouette enjoy a moment in the high-fashion spotlight, from Scholls' 'nanny' clog collaboration with Balenciaga to Ecco's partnership with Natacha Ramsay-Levi.'
So, which are the ugliest shoes of all? We present an unofficial ranking…
The good, the divisive and the ugly
Ranked from the least offensive
8. Birkenstocks
Boston clogs, £150, Birkenstock
The least ugly of the ugly shoe brigade and, as recent sales figures illustrate, still firmly in demand. The list of collaborations alone proves their fashion credentials – Proenza Schouler, Jil Sander, Dior, Manolo Blahnik and more. It's hard to believe that 'Birkies' used to be the preserve of Surreyites holidaying in Cornwall. It's much easier to slip them on – with or without socks – and enjoy the comfort and durability of the shoes that made ugliness aspirational in the first place.
7. Sheer flats
Mesh flats, £370, Dear Frances
Sheer flats, which offer a glimpse of the (ideally pedicured) foot beneath through mesh or woven fabric, once felt daring and divisive. Now they can be picked up at M&S alongside your groceries, meaning those who find them ugly might just have to accept them at this point. They've retained their fashion appeal too, with elegant heeled iterations at Dear Frances and searches for Alaïa's cult mesh style, which launched a thousand copycats, increasing by more than 350 per cent in the last three months.
6. Hiking sandals
Sandals, £40 (down from £50), Teva at M&S
Teva is the name to know in this category, born when a river guide attached two Velcro watchbands to an old pair of flip flops in the Grand Canyon in 1984. Their transition from hiking sandal to fashion statement was sealed when it was discovered that Mary-Kate and Ashley Olsen wear them regularly, rather than similar styles from their quiet luxury brand, The Row, which cost upward of £700. Tevas, in contrast, retail for around £40. A savvy saving could never be ugly.
5. Ghillies
Lace-up shoes, £375, Ganni
A newcomer to the ugly-chic scene – unless you grew up in Scotland or Ireland and had dancing lessons, that is – lace-up ghillies-inspired styles have been spotted on the catwalks since Chloé and Simone Rocha's spring/summer 2025 shows. They cropped up again at Ganni's autumn/winter 2025 show in Copenhagen and, by the look of the feet of the front row, fashion types are more than willing to embrace the Gaelic mood. They can be worn poking out of jeans if you're not ready to commit, but bonus points if you wear them over socks or tights à la Chloë Sevigny in her Ecco Biom C-Trail ghillie sneakers.
4. Chunky trainers
Air Max Muse trainers, £144.99, Nike
The chunky trainer has gone full circle. Thick soled styles went from no-go (see Steve Carell's character in the 2011 film Crazy Stupid Love being chastised by Ryan Gosling for his New Balances) to must-have thanks to Balenciaga's Triple S trainers, Nike's Air Max Muse style and gel-bottomed Asics. But just as they shook off the last vestiges of cringe and helped the dad shoe be reclaimed, slim trainers like Puma's Speedcats, Onitsuka Tigers and Alo Yoga's new Sunset Sneakers have slipped back onto the scene. What can we say – fashion is a fickle friend.
3. Sneakerinas
Trainers, £96 (down from £120), Ecco
The name is unappealing enough, but many iterations of this strange trend just feel a touch too try-hard. The best pairs lean more heavily into the 'ballerina' side of things – see the sleek Vivaia style favoured by Bella Hadid. Others feel part principal dancer, part professional hiker, but almost entirely unconvincing.
2. Crocs
Crocs, £49.99, Crocs
Crocs have enjoyed various moments in the fashion spotlight over the years thanks to collaborations with Balenciaga and Simone Rocha, and celebrity appearances including Brooke Shields on the Tony Awards red carpet in 2024. But that was aeons ago in fashion history, and the brand's latest partnership with Jean Paul Gaultier is an abomination. Now, there's just no getting past the fact that they're not very attractive. Special dispensation if you're pairing them with medical scrubs, gardening, or happen to be under the age of 10. David Hockney and Tracey Emin, both famously fans of the rubber clog, are also excused.
1. Five-finger shoes
FiveFingers, £110, Vibram
Sorry, but we're just not convinced. Vibram's proudly freaky FiveFingers were invented to deliver a 'barefoot' experience for sports like sailing and hiking. Fair enough, but why are some members of the style set insisting they're necessary for navigating the uneven terrain of the streets outside fashion shows? Nobody needs to see the outline of your toes on the bus on the way home. If you must divide them, start saving for a more palatable option in the form of Maison Margiela's distinctive Tabi shoes (yours for £820).