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Chic Critique: How the stiletto fell from great heights

To heel or not to heel? H! Fashion's Tania Leslau delves into the stilettos' fashionable rise and fall 

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Tania Leslau
Fashion features writer
2 days ago
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Whoever said ‘the higher the heel the closer to heaven’ needs a reality check.

Stilettos are a love-hate relationship in footwear form - an artful blend of pain, power, and peril. They’re the shoes that make you taller, more poised, and often a little unsteady, like a fabulous giraffe on roller skates. It’s a glide or go over situation.

My stiletto-based scenario typically looks like the latter. Standing at 5’10 already, I never look to the toweringly thin structure for my after hours soirées. Kitten heels call to me with their kitsch exterior and comfort-forward design, two factors stilettos greatly lack. 

Loewe shoes© Imaxtree
Loewe AW23

As someone who ended up in hospital with ligament damage from falling off the pavement in Nike Air Force, high heels are not my friend. Suave as they are, the kicks bring with them all sorts of podiatric woes. Blisters, sore arches and ankle sprains are all part and parcel of making your legs look longer. After all, the shoes were originally named after a type of slender-bladed dagger used in Renaissance Italy. A point PRs may want to skim over. 

Bar the odd Christmas party, stilettos are becoming increasingly absent. Women are opting for low heels with high impact, as evidenced by recent fashion week sightings and celebrity outings. 

Burberry AW23© Imaxtree
Burberry AW23
Gucci SS25© Imaxtree
Gucci SS25
Prada AW23© Getty
Prada AW23

Gucci championed wedge designs for its SS25 collection, while Prada pushed point-toes with racer stripe accents. A few seasons earlier, Miu Miu pioneered the divisive heeled thong boot for SS23, as Fendi sent silver bubble heel constructions down the catwalk. 

Versace famously pivoted to embrace a loafer-inspired platform heel, coveted by Nicola Peltz Beckham and Dua Lipa. Marc Jacobs’ ‘Kiki Multi Buckle Boots,’ earned a place in every fashion editor’s wardrobe, proving the stiletto to be a somewhat dull choice.

Emilie Joseph in pink feather trousers© Getty
Emilie Joseph

Now, as a writer, one has to be aware of personal bias. To certify that I wasn’t alone in my dislike of stilettos, I turned the H! Fashion team. Associate Editor Clare offered a hearty dose of reassurance: “I never wear stilettos because I can't bear being uncomfortable for more than four seconds at one time. If it was acceptable to go to parties in your slippers, I absolutely would.”

Editor Natalie agreed: "I’ve traded my stilettos for metallic platforms recently. You get to keep the stature - but magically, the chunkier sole and heel makes them less painful Obviously stilettos will always have a place in our wardrobes, but I won't wear anything that I can't walk around in anymore. Those days are behind us."

Dua Lipa© @dualipa
Dua Lipa

However, Lifestyle and Fashion Writer Lauren was quick to disagree: "I will never tire of the classic stiletto. Granted, they're not the most comfortable of shoes, but the slender heel is universally chic and a pointed court heel takes any look to new levels of sophistication."

Drat, I thought. She has a point about the patent point toes. Elsa Hosk, Kendall Jenner and Hailey Bieber do look pretty damn good in them.

Elsa Hosk in shirt dress© Getty
Elsa Hosk
 Hailey Bieber in a LBD© Getty
Hailey Bieber

No matter, I stand by the theory that there are more playful silhouettes to toy with. Yes, the Saint Laurent variations are beautiful, yet most can’t afford to drop upwards of £500, meaning one has to play the high street game. Which, when it comes to stilettos, is risky business. One, they may simply snap on you and two, because there’s always an unnecessary diamante buckle or embellishment ready to ruin a potentially great pair of shoes. 

It seems the general public agree. According to data, sales of high heels dropped by 65 per cent year-over-year during the second quarter of 2020, while sales of flats and sneakers rocketed. In September 2024, Birkenstock reported a record third quarter thanks to increased demand across all regions, marking a revenue of £474.8m. Adidas Gazelles increased 143 per cent in popularity in 2023, while ballet flats and biker boots dominated The Lyst Index’s most popular products for Q2 2024.

People want comfort over the extra inches. I say it’s time to usher in a new era of anti-stiletto styles and bring back unadulterated fun, fabulous and functional silhouettes. 

How to wear stilettos:

woman in heels and socks© Getty
With socks for a kitsch edge
women in heels burgundy leather© Getty
Cut from a patent burgundy leather
model in heels and  tights© Getty
With tights
womn in gold heels© Getty
For a metallic pop

How to style stilettos:

  • DRESS: Ella Mini Dress, £790, DOUBLE J
  • BAG: Anika Bag, £129, JW PEI
  • SHOES: Saint Laurent Lee 110mm Patent-Leather Slingback Pumps, £945, FARFETCH

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