The daughters of the Duchess of York have become known for their stylish fashion choices at important royal gatherings. However, their journey to becoming fashion icons has been a gradual process of refining their looks over the years.

Fans who have followed Princesses Beatrice and Eugenie may be surprised to see how their style has evolved from their earlier appearances to their current polished and sophisticated ensembles.

In the early 2000s, the princesses embraced the fashion trends of the time, which included wearing oversized dress shirts paired with skinny jeans, bold statement belts, and dramatic side-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).

While both faced criticisms for the ‘awkward’ fits, often marked by seemingly shapeless silhouettes and plain colours – with particularly memorable Philip Treacy hats worn to the Prince and Princess of Wales’s royal wedding (pictured) – they have certainly had the last word

Fans may be surprised by past appearances from Princesses Beatrice and Eugenie, which are a far cry from their sleek and sophisticated ensembles today

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. Pictured in 2008

The pair have also learned to lean into the bright colours and patterns that accentuate and complement their tones. Pictured in 2023

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. 

Beatrice has refined her look over the last years, adding some stylish new season pieces, together with recycling her faithful accessories and wardrobe essentials. Both pictured in 2023

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. Pictured in 2023

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

Last year, Beatrice, 36, topped Tatler’s best-dressed list – as the society bible praised her for being ‘a beacon of sartorial elegance’. Pictured in 2022

She has evolved her palette into more flattering colours for her gowns. Picutred at King Charles’s Coronation last year

Beatrice and Eugenie sporting striking ensembles at the Coronation Big Lunch in Chalfont St Giles in 2023

Eugenie, pictured in a figure-hugging all-scarlet ensemble, as she attended Ascot earlier this month  

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 

‘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. 

Before images from the early 2000s show Beatrice discovering the throws of noughties fashion in ill-fitting pastel babydoll dresses and audacious patterns. Pictured in 2005

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

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

Beatrice and Eugenie, pictured with their mother, sporting outfits which have since been dubbed ‘awkward’ in 2009

The sisters pictured in 2009, with their mother, in black outfits. They have since enjoyed playing with more colourful looks

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.