Stilettos are back – here’s how to master them

Dizzying heels that make your bottom wiggle and your legs look endless are no longer relegated to the corporate world

This trend can still be an intimidating one

Stilettos have languished in the wilderness since the fashion set made the era-defining transition from ultra-spindly heels to trainers and Birkenstocks a decade ago – but at London Fashion Week they were back, and higher than ever.

Last weekend’s shows were, of course, overshadowed by a far more seismic event: the Queen’s lying in state and funeral. Fashion was not at the front of everyone’s minds, but the elegance of the royal women’s outfits was an undeniable advertisement for the return of grown-up shoes. 

The Princess of Wales and the Duchess of Sussex in particular looked glossily glamorous in all-black – but it was the stilettos worn with sheer tights that gave their outfits a high-fashion feel.

The Princess of Wales is clearly a stiletto pro Credit: Mark Cuthbert/UK Press via Getty Images

So brace yourselves. Vertiginous heels that make your bottom wiggle and your legs look endless are back: think power dressing for the final two decades of the 20th century. Remember those films from the 1980s, where sirens would strut into boardrooms and bedrooms in the sheerest of black tights and sky-high black heels and every man would fall at their feet in a puddle? 

Stilettos may have been relegated to the corporate world ever since but – at the collections at Schiaparelli and Balenciaga couture, Chanel Cruise, Yves Saint Laurent, Sportmax ready-to-wear and Valentino pre-fall – there was one undeniable theme: the return of sex and glamour. And they showed this by styling their mini-skirts, power suits and pencil skirts with sheer tights and towering heels. 

The Princess of Wales and the Duchess of Sussex are clearly stiletto pros and make the trend look more wearable than it arguably is. I can’t have been the only person noting the height of their heels on every occasion over the past 10 days and wondering quite how they did it; personally, I think heels that high and tights that sheer will always require some kind of chauffeur, whether that means a royal steward in a Rolls-Royce or an Uber driver in a Prius. 

“When it comes to the tights, I would also go for 15 or even 20 denier – while 10 can look great, they ladder so easily, they can be stressful,” says Greenhill. “And, if you can, opt for the most expensive shoes you can afford. The shoes because they’re always more comfortable; the tights because very cheap styles can look almost green.”

The catwalk has seen the return of mini-skirts, power suits and pencil skirts with sheer tights and vertiginous heels Credit: Stephane Cardinale - Corbis

As for how you walk in them – there are a few tricks that the royal women must be aware of: first, ensure your shoes are neither too big nor too small. If your feet have a tendency to slip out of the shoe, choose a style with a strap around the ankle or across the top of your foot, as they help keep the foot in place. Alternatively, a spritz of hairspray inside the shoe can also help keep silky stockings and feet more firmly in place.

Gel insoles (Scholl Party Feet, £5.50, boots.com) can relieve pain in the ball of the foot, while many A-listers – including Sharon Stone – swear by topical numbing sprays and gels. One fashion editor friend uses RelaxInk Tattoo Numbing Spray (£11.39, from amazon.co.uk).

A less extreme tactic? Stretch your ankles before you set out and place your heel down on the ground first, followed by your toe as it puts far less stress on the top of your foot. If you’re worried about tripping, look ahead rather than at your feet.

Painful feet aside, this trend can still be an intimidating one. The association with the glamazons of the past is all very well if you like your legs – but, if you don’t, it can be tempting to turn to less attention-seeking opaques and kitten heels instead. Before you do, consider how flattering sheer tights are, as they slim your calves and ankles, while giving legs some definition. 

I’ve always been wedded to flat shoes, but the pandemic showed me the extent to which fashion can be a mood-enhancing substance. This winter I plan on wearing heels that insist on being shown a good time.

Heels to go 

  • Comfy stiletto: Patent leather, £245,
  • The slingback stiletto: Suede slingbacks, £75,
  • Inexpensive stiletto: Ankle strap, £32.99, Zara
  • Fashion stiletto: Brown leather, £565, Christian Louboutin

Are you thrilled by the return of stilettos? Tell us why in the comments section below