I'm a fashion expert – here are Princess Eugenie's fashion fails and stylish wins

For the past decade, royal observers have watched Princess Eugenie and her older sister Beatrice stumble through their 20s leaving a trail of style blunders.

The pair received an onslaught of criticism for their experimental fashion choices at Kate and Prince William’s wedding in 2011 where Eugenie’s fussy blue Vivienne Westwood outfit widely missed the mark.

British superstylist Charlie Anderson was brought in to spend a year working with the York sisters to ‘turn around’ their image who many said had been following the style example set by their mother, Sarah Ferguson.

After a chic fashion U-turn, Princess Eugenie’s style clambered its way to becoming youthful yet sophisticated, even getting a small circle tattoo behind her ear reportedly in honour of her grandmother, the late Queen.

The princess achieved her ultimate sartorial triumph at her wedding to husband Jack Brooksbank in 2018 when she wowed in an elegant V-neck Peter Pilotto gown with a low back displaying the scars from her childhood operation for scoliosis.

Here, celebrity stylist and royal fashion expert Miranda Holder takes us through Eugenie’s fashion journey – from clueless to cool… 

Princess Eugenie triumphed in a stunning Peter Pilotto gown for her wedding to James Brooksbank in 2018

Eugenie showed off the small circle tattoo behind her ear at the Platinum Jubilee celebrations last year

2011 vs. 2018 

Miranda’s verdict on outfit one: ‘In the first outfit there was simply too much going on.

‘Princess Eugenie’s frame was simply swamped by a riot of different silhouettes, shapes and styles, all competing for attention and leaving the Princess looking more like a Pantomime character than an elegant Royal. 

Princess Eugenie was criticised for her choice of outfit for Kate and William’s wedding in 2011, donning a garish blue Vivienne Westwood suit with an asymmetrical hemline and an over-the-top feathered and floral Philip Treacy hat. By contrast, the princess looked elegant for Meghan and Harry’s wedding seven years later, wearing a flattering Gainsbourg pastel blue dress partnered with a simple hat

Stylist Miranda Holder shares her verdict on Eugenie’s fashion transformation

‘The shoes didn’t really go with the rest of the outfit and felt like a last minute addition, the skirt and corset top were overdone and felt extremely dated, the hat might have been ok with a totally different look, but the overall effect of this combination is far from flattering. 

‘It is clear that Eugenie hadn’t invested time in determining what her own personal style was at this point as the outfit feels more dressing up box, rather than a true reflection of the woman wearing the outfit.’

Outfit two: ‘Seven years on, we are seeing a more sophisticated Eugenie who is paring things right back. 

‘Gone are the fulsome embellishments and details and instead we have clean lines which feel far more chic. 

‘The shoes are daintier and complement her shapely legs, the vintage-inspired shift dress shows off her hourglass figure and the headband is not overpowering. 

‘The effect is more subtle and feminine, showcasing the Princess who looks confident and happy in this style.’

2013 vs. 2019

The princess made the other guests green with envy at Ladies Day in 2019 in a flowing teal dress with a small cutout for Royal Ascot Ladies Day in 2019. The sophisticated choice was an improvement on the green ensemble with a tight-fitting jacket and purple fascinator which the princess wore to celebrate 60th anniversary of the Queen’s coronation in 2013

Miranda’s verdict: ‘The earlier outfit again just feels very dated, even for 2013. 

‘Although the biker-style jacket complemented Eugenie’s hourglass curves, the entire effect is more air hostess rather than wedding guest. 

‘The wide lapels on the jacket made her bust look larger and the boxiness of the dress underneath it has a squaring off effect, which adds to the frumpiness. 

‘The jacquard fabric of the jacket resembled a curtain material and the black shoes and plum hat were mismatched which made the entire ensemble look like a bit of an accident. 

‘It is clear that at this time, Eugenie hadn’t really “found herself” when it comes to fashion, none of her bubbly personality shone through with this look, which feels far too formal and constrained. 

‘Although this is the earlier photograph, the look is actually making her look older!’

Outfit two: ‘The 2019 look is so much better – for starters, it’s far more contemporary! 

‘The accessories are mismatched in colour but they still all complement each other, and the result is modern and fresh. 

‘The statement hat elongates her frame, the handkerchief hem of the skirt feels floaty and feminine and Eugenie’s figure is balanced with the waist nipping belt. 

‘The Princess’s style has blossomed and she exudes poise and elegance.’

2016 vs. 2018 

Eugenie missed the summer memo for Ascot in 2016 opting for a black ensemble with a skirt decorated with oversized daffodils. But for the announcement of her engagement to James Brooksbank in 2018, she chose an elegant high-neck Erdem dress with a more subtle floral pattern and partnered with pretty high heels with a bow.

Miranda’s verdict: ‘We definitely have a pattern here! 

‘Eugenie was simply doing too much in the first outfit in 2016 and the result was a cluttered, fussy and veering towards dowdy – once again she ironically appears older in the earlier photograph. 

‘The large floral print on the A line skirt is very old-fashioned and makes her bottom half appear bigger than it is, and the matching top was just too modest which in this case looks severe. 

‘I like the idea of the white collar and cuffs to lift the look, but sadly with everything else it’s just too busy. 

‘The hat with this look also made the Princess look wider, she would have done better with a more vertical style which adds height. 

‘I get the feeling once again that Eugenie was playing a role here, and didn’t really know who she was or what to wear to reflect that persona.’

Outfit two: ‘The second picture is like chalk to the other’s cheese. 

‘Eugenie has embraced the art of keeping things simple, with a fun, flirty midnight floral dress in a much smaller and infinitely more flattering print. 

‘The skirt is a more flattering length showing off “more leg” and the little kick flounce at the bottom balances out her hips. 

‘Eugenie has wisely balanced out this look and kept her top half more modestly dressed as her pins are on display – and she looks great. 

‘In the couple of years that have passed since both these photographs were taken, the Princess has clearly become more comfortable both in herself as a person, and her figure, and as a result she is glowing.’

2009 vs. 2019 

A young Princess Eugenie wore a silk nude-coloured dress with an extravagant lace neckline for the world premiere of the Young Victoria in Leicester Square in 2009. In a manifestation of the princess’ style journey, she opted for a flattering dress of the same colour for a Royal Garden Party in 2019 with a v-neck and pleated skirt

Miranda’s verdict: ‘Nude shades are notoriously hard for most of us to wear, so the Princess had a tough call here to start with. 

‘I can see where she was trying to go with look 1 in 2019, but the shoes were too clumpy and not strappy enough, and the pleats of the double-layered dress just make it look cheap – as does the fabric, particularly under the flash lights of the camera. 

‘The Princess would have benefitted from working with a professional stylist here, who would have camera-tested the outfit beforehand (and probably chosen something else).’

Outfit two: ‘Fast forward ten years and the nude look is far more flattering for the Princess. The simple, wrap-style dress suits all body shapes and perfectly complements Eugenie’s frame, her waist is accentuated and the V-neck opens up the upper part of the dress which balances the heavier sleeve. 

‘Far better material. I’m not entirely convinced about the hat.’

2012 vs. 2022

The Duke of York’s daughter loves to wear bright colours but her silk purple dress for the Service of Thanksgiving for the Queen’s Diamond Jubilee in 2012 was wrinkled with a deep scoop neck and bell-shaped skirt. But for the Service of Thanksgiving for the Queen’s Platinum Jubilee, the princess stunned in a flowing orange ankle-length gown, bringing vibrancy and sophistication to the event

Miranda’s verdict: ‘The purple outfit feels very 1960s Pierre Cardin to me, once again ageing the Princess, however, I really like the boat neck on her, as well as that sleeve length and I like the pairing with the grey accessories – she is almost there, but not quite. 

‘This photograph was taken in 2012, so we know from the other images that Eugenie is really starting to develop her own sense of style and become more confident, and this is shown in her decision to wear such a bold tone of purple, which is fab.’

Outfit two: ‘I love this orange look. Eugenie has ‘grounded it’ with black accessories which look super-sophisticated and although this dress is quite modest, which could have the effect of appearing frumpy, the zing of the bright orange counteracts that, making it a head turning look. 

‘The simple up-do for her hair is also perfect, so as not to compete with such a striking ensemble. 

‘In these later years, Eugenie has evolved from being more confident and comfortable with her fashion choices to embodying the epitome of chic.’

2017 vs. 2019 

Patterned dresses mark the princess’ position as a young royal but some looks have been more successful than others. Her Burberry dress for the Serpentine Gallery summer party in 2017 was a confusing mixture of patterns whereas her two-tone Peter Pilotto gown with simple gold decoration for The Animal Ball Art Show two years later emphasised her rosy complexion 

Miranda’s verdict: ‘Princess Eugenie did love her shift dresses! 

‘This is from 2017, and we know that Eugenie was really starting to hone her sartorial choices by now. 

‘This one is at least belted which gives her some shape, but the round neck, boxy skirt and cap sleeves again make her look squarer. 

‘At least she hasn’t gone overboard with the accessories – overall this is a much better outfit when compared to her 2011 ensembles!’

Outfit two: ‘Two years on and we see a more grown up and glamorous Princess, it’s another relatively modest look, but we have buckets of sex-appeal in the bare shoulders, spiked stilettos and semi-sheer fabric. 

‘The studs on the shoes provide the perfect amount of edge to stop this pretty look from feeling too girly. I love the ombre tones of the dress too.’

2008 vs. 2019 

A royal princess would not complete without her fascinator. The simple slanted hat that Eugnie wore for Trooping the Colour in 2019 was much more flattering than her bold purple choice with tall flowers for Ascot in 2008

Miranda’s verdict: ‘This is a very early outfit from Eugenie and it shows. 

‘It feels slightly equestrian-inspired, the jacket, hat and gloves reminiscent of a rider competing in a showjumping contest and the result is a very heavy look that completely overpowers the Princess. 

‘With the high neck, long sleeves, heavy hat and gloves, we cannot even glimpse the “real Eugenie” underneath it all. 

‘The hat is the finishing touch, but makes the outfit far worse, being way too fussy and complicated. Once again the look is dated and ageing.’

Outfit two: ‘The second look is from 2019 and we can see a far lighter, pretty dress, which despite being voluminous in terms of fabric, shows off Princess Eugenie’s slender wrists, which helps to keep everything in proportion as well as being a more contemporary silhouette which makes Eugenie look younger. 

‘The slim hat is an excellent choice, worn at quite a sharp angle, it contrasts beautifully with the lines of the dress whilst adding flattering height. Simple but effective.’

2017 vs. 2019 

The princess looked summer-chic for the wedding of Daisy Jenks and Charlie van Straubenzee in 2019, pairing her pastel blue midi dress with a flattering cropped white jacket which complemented her outfit. The colour coordination was less successful in 2017 when Eugenie chose a striking blue dress paired with an orange hat for the Buckingham Palace Garden Party

Miranda’s verdict: ‘The first look is far better than many of the infamous busy looks from Eugenie’s earlier years, but even with the more minimal aesthetic which suits the Princess, the accessories are mismatched. 

‘This can be a good thing, but in this case it looks a little haphazard. 

‘The neckline is too angular for Eugenie’s curvy figure, the cap sleeves too severe and unflattering. The on the knee skirt length is also a bit matronly.’

Outfit two: ‘In the second look the Princess is still keeping things minimal, but is also channelling easy-breezy Summer style. 

‘She looks effortless, relaxed and happy in chic ivory and pale blue and has made the look more fun with statement sunnies. 

‘I’m assuming the bag she is holding belongs to someone else as it’s totally incongruous with everything else that she’s wearing.’

2016 vs. 2022

Eugenie’s attempt at white formalwear for summer went wrong in 2016 when she opted for a loose-fitting white top with an unflattering knee-length floral skirt for the Not Forgotten Association garden party in 2016. But last year, the princess brought fun to the Platinum Jubilee celebrations with a figure-flattering white dress lined with patriotic red, white and blue tassels

Miranda’s verdict: ‘This look from 2016 was definitely a miss. 

‘Despite the dress being sleeveless with a V neck in look 1, the garment still looks too heavy on Eugenie. 

‘The loose fit does absolutely nothing for her figure, the ankle straps on the shows make her legs look wider and the low positioning of the hat cuts her face off making her look shorter. 

‘It ages the Princess by at least 10 years.’

Outfit two: ‘In the second look, Eugenie looks more modern and sophisticated. 

‘A classic white dress is updated by the red piping detail which lifts a very boring silhouette into something more playful – and – most crucially for the Princess, her waist is defined.’

2016 vs. 2022 

Eugenie has developed a chic ‘going out’ style, stepping out last year in a little black dress with a long checked coat and knee high boots. The attire was a far cry from Eugenie’s old style, going to an after party for the play ‘Deathwatch’ in 2016 in a dress that did nothing for her figure teamed with a biker jacket

Miranda’s verdict: ‘The first look from 2016 is definitely showing us that Eugenie’s style is evolving. 

‘Gone are the cluttered, fussy frills of the past and instead we see a simple look that feels fresher even if it’s still a little old-fashioned.

‘The skirt length is a little unflattering – I would have raised it by a couple of inches to show off Eugenie’s shapely legs – and the ankle boots also make Eugenie’s legs look a little heavier than they are.’

Outfit two: ‘Jump to 2022 and we are seeing a sassier, more confident Eugenie. 

‘A micro-mini showing ample leg and high boots are a bold but winning choice, and the artful layering of the jacket and scarf with the oversized bag make her look like a savvy fashionista. 

‘The result is effortless confidence and style.’

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