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stiletto high heel shoes© Jeremy Moeller

The best stiletto high heels for weddings, parties & race days

Stylish stilettos for every special event

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Hollie Brotherton
Lifestyle & Commerce Senior Writer
June 14, 2024
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Is there anything that makes you feel more special and ready for a big event than putting on a pair of killer stiletto heels? 

While they can quite literally be painful if you spend too long on your feet, every now and then it's worth it for that perfect outfit. 

These days I find they're more comfortable than ever too, with padded insoles on many high street and designer styles. Plus, if in doubt, carry a pair of ballet flats in your bag.

With summer fast approaching, it's likely you have a day at the races, a wedding, hen do or some form of party in your diary in the coming months, so a pair of stiletto high heel shoes is a must to take you through the season. 

Royals wearing stilettos at Ascot

[L-R Princess Diana, Princess Kate, Duchess Sophie, Princess Beatrice]
[L-R Princess Diana, Princess Kate, Duchess Sophie, Princess Beatrice]

Unsure of what shoes to wear to Royal Ascot? If you're heading there next week, it might be useful to know that stilettos are the heels of choice for the likes of Princess Kate and Duchess Sophie. The royal ladies tend to choose style over comfort for a day at the races, most often seen in stiletto court shoes. Even Princess Diana wore a pair with her skirt suit ensemble back in 1985.

Celebrities wearing stiletto heels

[L-R Victoria Beckham, Michelle Keegan, Hailey Bieber, Meghan Markle]
[L-R Victoria Beckham, Michelle Keegan, Hailey Bieber, Meghan Markle]

Stilettos are also a go-to for celebrities at events and on the red carpet. VB loves her heels - and I'm obsessed with the strappy inclined pair from her Mango collection - while Meghan Markle has worn sky high stilettos on multiple occasions, including announcing her engagement to Prince Harry.

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Hailey Bieber wears them with everything from mini skirts to demure knitted midis, and Michelle Keegan loves a pointed toe pair with dresses and trouser suits.

How I chose the best stiletto heels

  • Style: From court shoes to strappy sandals, I've included stilettos to suit every style in this edit.
  • Price: I've also found shoes for a range of budgets, from Jimmy Choos and Louboutins to pairs from ASOS and Aldo.
  • Heel height: I've only included heels 3.5 inches and higher. Head here for the best mid-height heels.

Christian Louboutin So Kate 120 Pumps

Louboutin stiletto heels

  • Sizes available: IT 34.5-43
  • Colours available: Black, Beige, Snake Print
  • Heel height: 5 inches

If you're looking to invest in a designer pair, stilettos don't get much more timeless than Louboutins. Made in Italy, this classic So Kate style feature a pointed toe and the brand's signature lacquered red soles.

Manolo Blahnik Hangisi 105 Silk-Satin Pumps

Manolos

  • Sizes available: IT 35-42
  • Colours available: Blue, Black, Red
  • Heel height: 4 inches

Channel Carrie Bradshaw - Queen of Manolos - in her exact cobalt blue Hangisi pair. Made from silk-satin, they're crystal embellished with a pointed toe.

Jimmy Choo Saeda 100 Embellished Satin Pumps

Jimmy Choo stilettos

  • Sizes available: UK 2-10
  • Colours available: White
  • Heel height: 4 inches

How dreamy are these Jimmy Choo stilettos? Whether you're accessorising an LBD or an all-white outfit, with their crystal anklet and sheer detail they'll make the most stunning finishing touch.

Carvela Kross Stiletto Heel Court Shoes

Carvela stiletto heels

Sizes available: UK 3-8

Colours available: Black, Blush, White

Heel height: 3.5 inches

A pair of classic stiletto court shoes are a must in any high heel collection. Made from soft suede, Carvela's have a pointed toe and thick straps with durable uppers for years of wear.

Mango x Victoria Beckham Leather Heeled Sandals

Mango heels

  • Sizes available: UK 3-8
  • Colours available: White, Burgundy, Black
  • Heel height: 4.1 inches

From Mango's collaboration with Victoria Beckham comes these very chic stiletto heels. Made from 100% leather, they feature a unique incline heel and barely-there straps. 

ASOS DESIGN Nelly High Heeled Sandals

ASOS gold heels

  • Sizes available: UK 2-13
  • Colours available: Rose Gold, Natural Linen
  • Heel height: 4.1 inches

These affordable stiletto heels from ASOS have a strappy, open-toe design with a pin-buckle fastening. Both colourways will complement all of your occasionwear this season.

Aldo Barrona Heeled Sandals

Aldo silver heels

  • Sizes available: UK 3-9.5
  • Colours available: Silver, Pink
  • Heel height: 3.75 inches

These silver stilettos feature delicate rhinestone detail and a party-ready decorative bow. They're designed with Aldo's signature dual density comfort foam and padded insoles so you can dance in them all night.

Charles & Keith Pointed-Toe Spool-Heel Pumps

Charles & Keith heels

  • Sizes available: UK 1-8
  • Colours available: White, Silver
  • Heel height: 3.5 inches

Princess Kate has worn many similar pairs of white stiletto high heels to this trending pair from Charles & Keith - and I could see them on Michelle Keegan too. Set on sturdy spool heels, they're easier to walk in than most, making them perfect for a day at Royal Ascot.

H&M Heeled Strappy Sandals

H&M strappy sandals

  • Sizes available: UK 2-9
  • Colours available: Black, Red
  • Heel height: 3.5 inches

These luxe-looking strappy stiletto heel sandals could pass for being so much pricier than £29.99. The barely-there pair are an easy go-to with any occasionwear this summer. 

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