SS27’s Key Street-Style Memo? Walk Away From Flats

SS27’s Key Street-Style Memo? Walk Away From Flats

The spring/summer 2027 season might have involved less drama than last year’s Super September, which saw an unprecedented number of newly installed creative directors make their debuts, but, in many ways, the back-to-school mood has been harder to bunk off from. This time around has seen designers knuckling down as they start to really cement their visions for the houses they have been tasked with overhauling. We’ve witnessed Demna staging his third Gucci show in a simulacrum of the brand’s future store concept to hammer home the value of retail, and Jonathan Anderson offering up a lighter take on Dior’s codes in an effort to dress clients for a hotter planet. The uniform of show-goers has reflected this sharpening up of an industry that increasingly finds itself buffeted by unknown factors, from AI to climate change. Faced with an uncharted course, fashion, as illustrated by the street-style images Phil Oh and Acielle Tanbetova snap for , has decided its new uniform revolves around deliciously impractical, yet highly covetable heels.

Nothing gets the front row going quite like a statement shoe. “I recently wrote on Substack that I don’t see the point in smart flat shoes anymore, and I’m standing by that this fashion month,” says contributing senior fashion features editor Julia Hobbs, who has been living in a pair of gold glitter-encrusted Miu Miu favourites, and has spurred multiple fellow editors to scroll resale sites for the same Dororthy-adjacent footwear. “I don’t think of them as ‘accessories’; they set the whole tone of a look.”

But if last season’s street style was a visual representation of the game of oneupmanship taking place among editors bagging Matthieu Blazy’s first Chanel pumps, this season’s shoe game has centred around a simple rule: razor sharp and vertiginously high wins. These spiky stilettos take us back to a lost era, when fashion editors would rather quit smoking than be caught wearing flats. Victoria Beckham, who uttered the immortal line about not being able to concentrate in flats, had her husband film her climbing a stair master in a pair of six-inch clackers mere days ago (sadly the clip has since vanished into the black hole of expired Instagram Stories).

There’s reasoning behind all the blisters. Jimmy Choo devotee Osman Ahmed says that, aside from the “obvious lift in height, posture and mood”, a 100mm heel is an essential piece of fashion armour in an increasingly front-facing industry. “There have never been more cameras, tiny mics, drones, street-style photographers… You feel very much on show, even if you’re behind-the-scenes,” says Ahmed, adding: “Everyone is feeling incredibly . So maybe it helps us just feel a bit more polished, and like we’re putting our best footwear forward, for want of a better word.”

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So which heels are being road-tested by the fashion pack right now? Demna’s fan club has pledged allegiance to his new-era high-glam Gucci in his Donna pumps, with their dangerous heels and supersized horsebit hardware; while Prada-philes have swapped polite kitten heels for the “antiqued” leather lace-ups, which, per the brand, bring in “masculine details from the outdoor world”, or the flower-dotted designs boasting a punky spray-paint finish. Even Dior’s bow-bedecked sling-backs have bite, coming in a range of heel heights for those looking to give all that sweetness an extra lift.

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“A new kind of elegance – but for now,” is how Mrs Prada put it backstage at her autumn/winter 2026 show – a mandate we’re seeing trickle down already. “In the combination of the different elements, there is a choice and freedom, authority and agency for the woman wearing them.” Peep-toe, princessy or pointed, it’s the act of wearing stilettos that’s as important as the chosen style – like getting a blow-dry. “Heels just instantly make you feel a bit more put-together,” says Ahmed. “And they make your butt look better and your legs look longer, which is always a plus.”

See the best high heels on the spring/summer 2027 street-style circuit below.

  • Image may contain Clothing Coat Footwear High Heel Shoe Adult Person Fur Wristwatch Accessories Bag and Handbag
  • Image may contain Christian Jones Clothing Pants Adult Person Coat Footwear Shoe Blouse and Skirt
  • Image may contain Clothing Footwear Shoe Person Teen Long Sleeve Sleeve Coat Skirt Pants Sneaker and Car
  • Image may contain Person Teen Clothing Coat Jacket Accessories Bag Handbag Car Transportation and Vehicle
  • Image may contain Carine Roitfeld Clothing Footwear Shoe Coat Jacket High Heel Accessories Bag Handbag and Adult
  • Image may contain Adult Person Clothing Footwear Shoe Pedestrian Accessories Bag Handbag High Heel and Shorts
  • Image may contain Pamela Tom Person and Adult
  • Image may contain Clothing Pants Dress Coat Footwear Shoe Blazer Jacket Person Jeans and Formal Wear
  • Image may contain Leonie Hanne Clothing Footwear Shoe Adult Person High Heel Machine Wheel and Motorcycle
  • Image may contain Lashana Lynch Adult Person Clothing Skirt Pedestrian Accessories Bag Handbag Glasses and Jewelry
  • Image may contain Clothing Coat Jacket Person Walking Pedestrian Accessories Bag Handbag Adult Footwear and Shoe
  • Image may contain Saskia de Brauw Person Walking Adult Teen Clothing Formal Wear Suit Pants Footwear and Shoe
  • Image may contain Kamala Harris Adult Person Accessories Bag Handbag Teen Clothing Footwear Shoe and Skirt
  • Image may contain Antoine Daniel Clothing Pants Pedestrian Person Adult Jeans Standing Walking Footwear and Shoe
  • Image may contain Person Standing Clothing Skirt and Adult
  • Image may contain Person Walking Clothing Footwear Shoe Skirt Path People Adult Shorts City Road and Street
  • Image may contain Clothing Skirt Person Shorts Machine Wheel Adult Bag Accessories Handbag Footwear and Shoe
  • Image may contain Clothing Coat Pants Blazer Jacket Person Walking Formal Wear Adult Blonde Hair and Suit
  • Image may contain Beth Tweddle Clothing Skirt Accessories Bag Handbag Adult Person Electronics and Phone
  • Image may contain Juanita Bynum Clothing Footwear Shoe Adult Person Accessories Bag Handbag and High Heel
  • Image may contain Pedestrian Person Adult Car Transportation Vehicle Accessories Bag Handbag Clothing and Coat
  • Image may contain Jim Allchin Steve Johnson Person Accessories Sunglasses People Walking Adult Bag and Handbag

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