Ascot is upon us, which means royals, celebrities, and members of the public are descending on the racecourse in their droves to enjoy the racing in the blazing sunshine this week.
As a big event in the fashion calendar, all attendees have likely spent weeks or even months planning their outfits, especially since they have to follow specific rules set by Ascot. However, there are a handful of outliers who aren't afraid to break the rules, including Princess Diana.
Back in 1990, the mother-of-two attended Ascot alongside her husband, then-Prince Charles, and brother- and sister-in-law, Prince Andrew and Sarah Ferguson. Easily standing out from the crowd, the People's Princess wore a purple pencil skirt with a large buckled belt.
She added a lemon yellow top layered underneath a cherry red cropped jacket with boxy shoulder pads, tying together her colourful ensemble with a purple hat with a red trim.
© GettyDiana's decision not to wear a matching suit defies Ascot's set requirements, with the website stating those in the Royal Enclosure are expected to wear "a trouser suit of matching material and colour."
Another rule states: "A dress or skirt falling just above the knee or longer," but Diana also chose to take risks with her knee-length skirt.
Meanwhile, Sarah Ferguson coordinated with her sister-in-law in a ruby knee-length skirt and a buttoned jacket, which did match in colour, completing her look with a red and white striped hat.
Considering both royal ladies chose large statement hats, they ensured they did abide by one regulation, which dictates guests must wear a hat or a headpiece "with a minimum base diameter of 4 inches / 10cm."
Diana's 'armorial' style
© Getty ImagesOn the CNN podcast 'When Diana Met…', GQ fashion critic Rachel Tashjian explained: "There was this moment where I would say like maybe in the mid or late eighties where she begins to enter this phase that's widely referred to as Dynasty Di. That's when it's interesting because the press scrutiny is intensifying on her relationship," she said, referring to her separation from King Charles in 1992.
"The clothing begins to seem more armorial, you know, it becomes harder, the shoulder pads become more intense and and there's a lot of beading.
Princess Kate's Ascot wardrobe
© ShutterstockIt's Royal Ascot week and over on The HELLO! Royal Club, royal shopper Leanne teamed up with Samantha from the hugely popular Instagram account Royal Fashion Daily (formerly the Royal Fashion Police) to look back on Princess Kate’s Ascot wardrobe and offer some predictions on what the fashionable royal might opt for this week.
"There are a lot of sequins. So there's, there's that sort of sense of meaning to it, but also, she's just deepening these relationships, again, with these designers and particularly with Catherine Walker, who was really someone who designed both these kind of working skirt suits for her and did a number of gowns for her that are some of her most recognisable and memorable looks.
"This was a time where I think she was really trying to find her footing as a public figure and figure out what her purpose would really be."
Ascot fashion
© PA Images via Getty ImagesCatherine Walker continues to be a big hit with the royal family, with Ella Windsor opting for a petrol-blue embroidered coatdress – the same one worn by Kate in 2016 – to Ascot in 2025.
Other royals have also stepped out in royal-approved designers at the horse racing event, with Zara Tindall rocking a floral number from Anna Mason, and Carole Middleton wearing a lace butter yellow frock from ME+EM.
