10 Times Princess Anne Had A Royally Fun Time With Her Fashion

When you're one of the royals further down in the line for the throne and the world isn't always watching your every single move, you actually win the ultimate perk of the royal life: the freedom and resources to just have fun. Of course, though there are still royal duties and rules to adhere to, there seems to be more wiggle room. Princess Anne is a prime example of that. 

While there are so many avenues and aspects of life that wiggle room can be applied to, it's fun to see Princess Anne really have a royally fun time with her fashion. No, she's not wearing slitted dresses or chasing the biggest shorts trends for summer 2026, but her style is fun and undeniably captivating. Some royal fans even deem her the chicest royal when it comes to fashion, and after looking through her archives, it is easy to see why.

The princess' best looks just had to be shared, but with so many decades in front of the cameras, narrowing the looks down was no small task. That's why we limited our search range to her most iconic and fun looks from the '70s and onward. While no one is perfect and even the princess has occasionally been one of the royals caught wearing inappropriate outfits, most of her outfits are incredibly inspiring. From her vibrant colored coat at the 2026 Royal Ascot to her chic, casual off-duty look in the '70s, Princess Anne makes it clear that whatever you wear, wear it with confidence. 

The first look on this list is Princess Anne's très chic off-duty look from the '70s. Posing with both hands in her jean pockets, she exuded confidence while sporting a casual cool girl look during her visit to Russia in 1973. The look consisted of dark denim jeans and a blue-striped shirt. She didn't overdo it with her accessories either, as she cinched the look with a metallic buckle, brown leather belt and a navy-hue scarf around her neck. 

In 1984, Princess Anne visited Gambia and she chose to wear mixed chintzy florals, one of the most popular prints of the decade, with a utilitarian accessory for the perfect destination look. She styled a Liberty print dress with a straw-style safari helmet hat that was ideal for the tropical setting. The oversized dress with balloon sleeves was balanced by her all-white accessories, which included a delicate pearl choker necklace. The royal's oversized aviator sunglasses added a touch of modern edge to the overall ensemble. 

We love when a royal family member gets bold with their style choices, and Princess Anne's 1996 evening gala look at the Save the Children Festival of Trees proved that evening wear can be incredibly fun. She styled a black velvet maxi skirt with a highly structured and metallic silver floral brocade jacket, which featured dramatic puff shoulders (the perfect detailing for the '90s). The collar necklace encrusted with diamonds and brooch pinned to her lapel added the perfect amount of royal sparkle to the evening look. 

Sometimes, the best outfits in life are on repeat, even when you're royalty. Take Princess Anne's whimsically perfect tartan jacket, which seems to make a joyous comeback just in time for the holidays. The festive coat with green and red bands paired with the forest-green midi skirt and knee-high boots was first spotted on Christmas Day in 1998. The princess loved the look so much, she wore it again in 2004 at the annual Cheltenham Races. 

When you have a seamstress and tailor at your disposal, a wardrobe repeat isn't just a rewear. It's a reinvention. Take Princess Anne's Save the Children Festival of Trees pink satin gown from 2005, which was a rewear from the 1984 BAFTA awards. Her tailoring team deflated the shoulder pads and turned the puffy short sleeves into long, elegant sleeves with French cuffs. The oversized waist sash remained the same, and she swapped out the pearl accessories for everything diamond, including the earrings, the brooch, and the collar necklace. 

Having always danced to the beat of her own drums, Princess Anne proved she knows how to have a blast with her wardrobe even when the occasion doesn't seem fitting. For the Thomson International Financing Awards Dinner in 2005, the princess brought a striking dose of pastel and floral whimsy to the finance world event. The vibrant lavender gown with the perfect yellow and blue hue detailing on the bodice paired beautifully with a flowing silk skirt full of floral detailing. 

Bold patterns and neon colors aren't always the only way to show you're playing with fashion. Over the years, Princess Anne has proven that she knows how to have a royally fun time with patterns and color matching. Her outfit for the official tour at the London Boat Show in 2008 is the ultimate proof. The tailored, checkered coat in a flawless off-white cream complemented the rich navy skirt and scarf so perfectly. Each and every navy detail ties the fun, graphic look together. 

Princess Anne was clearly ahead of her time with her loyalty to wraparound sunglasses, which are one of the new sunglass trends you should try in summer 2026. Giving her royal outfits a twist by pairing them with aerodynamic sports frames from brands like Adidas and Oakley, she effortlessly bridges the gap between traditional luxury and modern streetwear. The otherwise classic suit and skirt combo that she wore to the 2018 Great Yorkshire Show got an instant edgier vibe thanks to her go-to red mirrored lenses. 

Women wearing menswear is one of the most timeless power moves in fashion. The late Princess Diana famously mastered the look herself in her unstoppable fashion queen era. Princess Anne put her own spin on the aesthetic and stepped out in a tailored, sage green pantsuit in 2024. While the look could have leaned almost too masculine, she cleverly subverted the sharp lines by tucking a vibrant, patterned silk scarf right into the neckline. 

For the Royal Ascot 2026, Princess Anne opted for one of the busiest looks she might have ever worn. The coat she wore featured a swirling abstract design and so many shades of color, including teal and purple. While many royal fans felt she was one of the worst dressed at the event, others praised her for going completely out of the box and owning such a bold and experimental look. The Princess Royal accessorized for the occasion and added a horse brooch to her colorful look.