Dubbed a famous fashion fail at the April wedding of William and Kate, Princess Eugenie has been transformed into the epitome of sophistication, says a leading celebrity stylist

It wasn’t just the bride and groom exerting global fascination at the April wedding of Prince William and Kate Middleton in 2011.

The svelte appearance of the chief bridesmaid, Kate’s sister Pippa, needs no further commentary.

And, then there were the York Princesses, Beatrice and Eugenie, who famously arrived sporting headgear of surprising – to put it kindly – flamboyance.  

In Eugenie’s case, an opulent Philip Treacy fascinator was paired with a striking Vivienne Westwood dress, a combination that led to as much criticism as praise.

And will, for some at least, live long in the memory.

Today, however, the 33-year-old mother-of-two has been transformed, according to celebrity stylist, Alex Longmore.

As the wedding anniversary approaches – and with it the anniversary of those eccentric fashion choices – Alex says:

‘I believe this new-found fashion confidence Princess Eugenie has, and her more stylised approach to dressing, is due to motherhood and how satisfied she is in the role of mum to two boys.’

‘Her outfit choices have evolved hugely in the last few years, favouring block colours over the tawdry floral prints of the past. She has also learnt what styles work with her figure’. 

Eugenie’s recent appearance at the Cheltenham Festival is a case in point, she says. 

‘The royal broke from tradition, and it worked. She pulled off what most women can only dream of – an individual look that is polished, chic and put together,’ Alex explains.

Stylist Charlie Anderson was enlisted to dress Eugenie and her sister following their royal wedding faux pas in 2011, sharing her fashion expertise with the siblings.

Charlie has said that both girls were ‘a delight to work with’ and that Eugenie, in particular, was open to new ideas.

‘Eugenie knew herself very well but was also willing to listen and try what I proposed,’ Charlie explained.

As she celebrates her birthday, we look back on the Princess’ top 20 style moments from over the years.

The Derby at Epsom Racecourse 

Eugenie’s polka dot dress from 2011 made a lasting impression.

For a day at Epsom Racecourse, she fully embraced a Carolina Herrera figure-hugging mini dress, paired with a complementary wide-brimmed hat.

It was stylist Charlie Anderson who sourced the show-stopping hat for the royal.

‘I convinced Eugenie to move away from fascinators and opt for wide-brimmed hats instead,’ Charlie explained.

‘I remember she already had a dress selected for Derby, but needed a hat, so I sourced one from Patricia Underwood – she looked gorgeous. 

‘A particular highlight for me was Eugenie being picked up by Italian Vogue for looking so good.’

We also have to credit the Princess for daring to wear sky-high heels on grass.

Royal Ascot 2013 

Princess Eugenie earned her style stripes at day one of Royal Ascot in 2013.

Matching with Beatrice in navy outfits by RED Valentino, Eugenie layered a cropped jacket, featuring puff shoulders and lace detailing, over an A-line skirt.

Keeping accessories to a minimum, she opted for mid-heeled court shoes, a simple clutch and bow-detailed hat. 

St Andrews 600th Anniversary Dinner 

In 2013, Princess Eugenie debuted a Paule Ka tricolour cocktail gown at Antonia Packard’s charity auction.

With its cleverly cut panels that accentuate the figure, this floor-length dress deserves praise.

It’s no surprise the Princess recycled it on two further occasions in 2014 and 2017.

End of Silence charity event 

Eugenie was the epitome of understated glamour in this BCBGMAXAZRIA gown, worn to the UNAIDS Gala during Art Basel 2016.

Combining an embellished halterneck and figure-skimming fit, the Viviane style proved to be the perfect choice for the glamorous occasion, especially when paired with a bold red lip. 

UNAIDS Gala 2016 

Designed with a silhouette reminiscent of the gown worn by Pippa Middleton at the royal wedding, Eugenie’s Alexander McQueen dress captivated our collective gaze. 

The wool-crepe design was effortlessly flattering with its cowl neck, draped detailing and midi length – not to mention the vivid red hue. 

Eugenie expertly styled her ensemble with black accessories and diamond drop earrings.

Royal Ascot 2016 

Another captivating Royal Ascot ensemble featured a Peter Pan sweater and voluminous floral skirt by Alice & Olivia.

To complete her race day outfit, Eugenie opted for simple black court shoes and a striking hand-stitched pearl hat by Nerida Fraiman.

This spectacular outfit certainly highlighted the Princess’ newfound confidence.

UNAIDS Gala 2017

For the 2017 UNAIDS Gala, Eugenie blossomed in a colourful floral dress by Erdem, previously worn during an interview with Harper’s Bazaar in 2016.

It hailed from the British designer’s pre-fall 2016 collection, which cited John Singer Sargent and Lord Snowdon as influences.

The intricate design was crafted from silk-organza with an alluring reveal and conceal effect that fell into a playful peplum hem.

The royal displayed her penchant for rewearing her favourite pieces as she later selected this dress for her official engagement photos with Jack Brooksbank. 

The Serpentine Gallery summer party 2017

Eugenie must be praised for injecting a burst of colour into her closet. 

The royal’s Mary Katrantzou jacquard dress could not have been more fitting for The Serpentine Gallery’s swanky summer soiree. 

She elevated her look with barely-there accessories, choosing Perspex court shoes and delicate jewellery.  

Vogue x Louis Vuitton GingerNutz celebration

Princess Eugenie bloomed in a Whistles dress at the Vogue x Louis Vuitton GingerNutz celebration in London. 

The timeless design incorporated a ruffled high neckline, cinched waist and semi-sheer sleeves, adorned with an autumnal print.

Eugenie earned further style points by adding suede knee-high boots and completing her look with a bold red lip.

The wedding of Prince Christian of Hanover and Alessandra de Osma

The Princess continued to embrace her newfound style at the wedding of Prince Christian of Hanover and Alessandra de Osma in Lima, Peru.

Belonging to Peter Pilotto’s pre-fall 2017 collection, her magnificent cold-shoulder dress was embroidered with paisley patterns by artist Jean Cocteau.

Teal side panels and side splits added to its allure, ensuring it was perfectly suited for the momentous occasion. 

The Serpentine Gallery summer party 2018 

In 2018, the trend of wearing dresses over trousers was all the rage, and Eugenie fully embraced it in this Roland Mouret creation.

The asymmetric design incorporated semi-transparent fabric and unstructured pleating, resulting in a breezy silhouette.

Eugenie’s confident demeanor, with her hand on her hip, was evident as she struck a pose next to her friend and singer, Ellie Goulding.

United Nations meeting

The royal brightened the boardroom when she attended a NEXUS Meeting held at the UN headquarters in New York.

Eugenie’s charming silk dress by Erdem boasted a ruffled collar, flattering fit and floaty hem. She has worn it a total of four times. 

The Princess added classic black patent pumps and dainty drop earrings, creating a flawless aesthetic. 

The wedding of Princess Eugenie and Jack Brooksbank 

The wedding of Princess Eugenie and Jack Brooksbank was everything one could envisage – it marked a turning point in the Princess’ style repertoire, too.

Held at the idyllic St. George’s Chapel, Windsor, the bride stunned in a bespoke ivory silk jacquard dress by Peter Pilotto. Its primary feature was a deep V-back, intended to show off Eugenie’s scar from scoliosis surgery that she had aged 12.

Her second ensemble was equally captivating: a custom-made gown by Zac Posen. The American designer is renowned for exquisite corsetry and draping techniques; the royal creation didn’t fall far from his signature aesthetic.

Crafted from silk plisse, the sculptural silhouette incorporated strong shoulders, a hand-pleated bodice and basque waistline that fell to the floor in a glamorous sweep.

Subtle detailing was added in the form of White Rose of York motifs, which adorned the shoulders while securing the cape. As for the alluring colour palette, it was said to ‘reflect that of an English rose’.

Animal Ball Art Show private viewing

Eugenie’s graceful appearance at the private viewing of the Animal Ball art show marked her first time wearing Peter Pilotto since her wedding day.

She chose a dazzling dress in shades of peach and turquoise, elevated by gold foil detailing.

The Princess reached new heights in Valentino Garavani Rockstud leather heels, boasting a metallic silver finish, while her brunette locks were styled in loose waves.

Together at Christmas carol service

At Kate Middleton’s Together at Christmas carol service, held at Westminster Abbey, Eugenie showcased her fashion prowess.

The royal wrapped up against the chill in a forest green wool cape by Chloe, teamed with Aquazzura leather knee-high boots.

One of her finest outerwear choices, the chic design exuded luxury with its double-breasted front and 60s-inspired shape.

Memorial service for the Duke of Edinburgh

Eugenie donned another floral Erdem dress, paired with Jimmy Choo pumps, at the memorial service for the Duke of Edinburgh.

With its high neckline, sharp knife-pleated skirt and bloomy motifs, this dress exuded glamour as it swept to the ankle.

The royal added an exquisite Emily London embellished headpiece, featuring a detachable bow. 

Vogue World: London 2023 

One of Princess Eugenie’s most noteworthy red carpet appearances took place at Vogue World: London 2023.

Celebrity Stylist Alex Longmore was one of many who praised the royal’s emerald outfit choice by Erdem.

‘She looked just like a movie star in Hollywood on the red carpet, complete with a directional hair style and dramatic make up,’ she said.

‘The jewellery with the silk dress was a bold choice but she was confident enough to pull the whole look off.

‘It was just like at her wedding to Jack Brooksbank when she exposed her scar down her back from her scoliosis surgery in the most stunning wedding dress.

‘Again, a bold move and a very brave one.’

The Anti Slavery Collective winter gala

Eugenie pulled out all the stops for her charity, The Anti Slavery Collective’s inaugural winter gala.

Standing out from the star-studded crowd, she wore a glamorous dress by Peter Pilotto, complemented by metallic strappy sandals that echoed the shiny gold buttons.

Dior Homme fall/winter 2024-25 show

Eugenie exuded elegance at the Dior Homme fall/winter 2024-25 show during Paris Couture Fashion Week in January.

The royal opted for a tailored wool dress and tuxedo-inspired coat at the prestigious event, staged in the courtyard of the 18th century École Militaire in Paris.

She accessorised with a pair of logo-laden slingbacks and the brand’s iconic Peekaboo ISeeU bag, while her sleek tresses fell over her shoulders.

‘Princess Eugenie looked confident and relaxed, fitting right in with the fashion pack,’ said Alex Longmore. 

Over the years, Eugenie has developed a strong relationship with the Dior’s creative director, Kim Jones, who also designs for Fendi. 

Cheltenham Festival 2024

At this year’s Cheltenham Festival, Eugenie opted for a camel knitted dress and off-white trench coat, both by Reiss, an Emily London felt fedora and suede boots from Penelope Chilvers.

‘The appearance confirmed that Princess Eugenie is very much winning on the style stakes,’ said Alex Longmore. 

‘She showcased an iconic look that was very elegant and somewhat directional for the normally very conservative Cheltenham.

‘She exudes confidence and feels routed in her appearance.’