The Duchess of York’s daughters often showcase some of the most stylish outfits during significant royal events, though their fashion sense has evolved over years of public appearances.

Supporters might find it surprising to look back at the earlier style choices of Princesses Beatrice and Eugenie, as they strongly differ from their polished and elegant looks today.

In the early 2000s, the sisters embraced the popular trends of that era, including oversized dress shirts paired with skinny jeans, bold statement belts, and dramatic side-swept fringes.

And while both faced mocking for the ‘awkward’ outfits, with shapeless silhouettes and plain colours – with particularly memorable Philip Treacy hats worn to the Prince and Princess of Wales’s wedding – they are now having the last laugh. 

Now, Prince Andrew’s two children have emerged as among The Firm’s best dressed, and always reliably well regarded to be the picture of elegance.

Just recently, Beatrice and Eugenie wowed with their appearances at the Royal Ascot, with theatrical Monique Lhuillier A-line frocks, scarlet gowns and even sleek trendy crop top and skirt pairings.

The pair have also learned to lean into the bright colours and patterns that accentuate and complement their tones. 

Last year, Beatrice, 36, topped Tatler’s best-dressed list – as the society bible praised her for being ‘a beacon of sartorial elegance’ by ‘pairing vintage-inspired cuts with fresh-from-the-catwalk glamour’, although it did note she was the ‘subject of much jest’ for the wedding hat (which both sisters are reported to have cried over).

The outlet said she had an ‘unfussy chic’ style, and praised her for ‘championing local labels like Edeline Lee’.

Beatrice has refined her look over the last years, adding some stylish new season pieces, together with recycling her faithful accessories and wardrobe essentials.

An important part of this gradual transformation is that, after experimenting with different styles, silhouettes and brands in the past, Beatrice has now found a theme – and a new confidence with upmarket fashion brands. 

Cue It-girl labels such as Self Portrait, Beulah, and Rebecca Vallance, which are taking centre stage alongside international labels Reem Acra, based in New York, and Monique Lhuillier on the West Coast.

This move towards high fashion marked a notable shift in the royal’s style, shelving the quirky headpieces and colours for a more streamlined touch.

Since turning 30, Beatrice has gradually found a fashion formula of her own and is now widely praised for her elegant yet flattering outfits.

Credit is due to her stylist, Olivia Buckingham, who also advises Poppy Delevingne and Nicky Hilton.

Dubbed society’s secret weapon, Olivia has introduced Beatrice to a series of go-to designers including the now defunct The Vampire’s Wife, Self Portrait, Monique Lhuillier and Emilia Wickstead, plus Manolo Blahnik and Chopard for accessories. 

‘I like to push my clients’ boundaries but also stick to their authentic codes,’ she previously told the Mail.

‘I don’t want it to be one-sided, what I enjoy is giving them creative freedom, then we meet in the middle and come up with a magical look.’

Before images from the early 2000s show Beatrice discovering the throws of noughties fashion in ill-fitting pastel babydoll dresses and audacious patterns.

In one snap from 2008, the royal is pictured next to supermodel Naomi Campbell sporting a daring ensemble that features both snake and cheetah-print designs.

Other times, Beatrice’s looks failed to land because of a more plain colour scheme or underwhelming design.

In 2009, she can be seen sporting a green linen dresses teamed with a simple belt and little else.

In contrast, in 2022, the royal showed how she has elevated her look in a more muted hue of the same colour, but this time bedazzled with sequins.

She has also focused more on styling her tresses, going from keeping her hair unstyled and free to presenting more glossy Hollywood-style curls and waves. 

And when it comes to Eugenie a similar evolution has taken place – with the Princess swapping out awkward noughties ensembles for elegant wardrobe staples that accentuate her beauty.

Speaking to the Mail in November, celebrity stylist, Alex Longmore says she has a ‘new-found fashion confidence’, which he believes is down her now being a mother 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,’ he explained. 

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,’ he explained.

Indeed, Eugenie’s flourishment is as remarkable as her sister’s. Throwback photos show her sporting awkwardly baggy dresses and sticking to black monochrome looks instead of adding a pop of contrast.

However, today, the Princess is known for her penchant of dual-tone looks, and much more curated eye when it comes to accessories.

Yesterday, the 35-year-old posed proudly in a short, brown top and cinched, high-waisted skirt for a photo – teaming the look with an ivory wide brim hat.