Why Princess Diana Is the Ultimate Vacation Style Icon

Princess Diana was a style icon for the ages—so much so that we still look to her today for style inspiration. Her effortlessly elegant persona, evolution from working royal to next-level ’90s celebrity, and willingness to take risks earned her a constant place on mood boards and in trend cycles well beyond the two decades she spent in the public eye. And while we adore everything about the people’s princess’s fashion moments—from the revenge dress to her iconic sweaters—the looks she wore on vacation were arguably some of the most fun and experimental of them all.

Away from official engagements—though never quite escaping the paparazzi—Diana challenged everything the world knew about royal style, playing with prints, silhouettes, and accessories in a way we’d never seen on a British princess before (or since). Ahead, we break down what made Princess Diana’s vacation style so iconic, complete with key pieces to embody her energy for yourself.

The Vacation Persona

From the very start, Diana loved a bold swimsuit, and her seaside looks just kept getting better over the years as she came into her own. Even while still married to Charles, the young princess’s statement-making swimwear choices—from floral bikinis to neon one-pieces—were a reprieve from everyday royal dress and provided early proof of her style icon status.

Whenever Princess Di was near a body of water, both her outfits and her overall energy were notably more relaxed and joyful—a reminder that the best way to build your vacation style is to break from your everyday aesthetic and dream big about who you want to be on your getaway. It’s truly freeing to leave your cares onshore and dive fully into your vacation fantasy, which might be why the fashion from luxe, travel-focused shows like The White Lotus has a hold on everyone today. Diana will forever be one of the strongest real-world examples of this, and it’s powerful to see that even though her style transformed a lot over the years, she always knew who she was by the sea.

Setting the Tone

Princess Diana’s everyday life was typically jam-packed with official engagements, and while her looks were always forward-thinking and creative, vacations let her experiment with more relaxed pieces and street style. Summer was when she tried some of her most memorable looks, like her sweatshirt-and–bike shorts uniform, and whenever she’d get away, the princess took style risks with pieces like the iconic leopard midi dress and plenty of statement-making graphic tees.

What really made these looks stand out was that Di was always a trendsetter. While her outfits included nods to plenty of trends, she also made bold, creative styling choices that would ultimately influence fashion at large. Her travel looks were casual and wearable but still full of unexpected choices: the kind of formula that highlights how we all can make our go-to vacation outfits feel fresh. This is exactly why off-duty style looks are far more than just examples of the best ’80s and ’90s fashion. Instead, they’re timeless sources of inspiration that can adapt to fit changing trends and various personal aesthetics.

Finishing Touches

No matter what type of vacation she was on or what look she was going for, Princess Diana was an expert at pulling her travel looks together with the perfect accessories. For sunglasses, she tried all different silhouettes while sticking to a classic, understated palette: the types of shades that are thriving again amid the quiet luxury moment. Often on vacation with sons William and Harry, the busy mother also gravitated toward practical, down-to-earth carry-on bags—usually in bright colors, and one even sporting the Harrods logo—which only further established her reputation as the people’s princess.

In a choice that would be unexpected for many people but also seems quintessentially royal, Diana would often wear luxe jewelry pieces even at her most dressed down. She kept it relatively simple (some go-tos included gold earrings and thin watch bands), but her subtle upgrades elevated many of her most laid-back looks into intentional statements. While Di may have had access to the best of the best, her vacation outfits proved that style is for everyone—all it takes is a little creativity.

Her Final Summer and The Crown

While Diana served forward-thinking, iconic off-duty looks throughout her entire time in the spotlight, she really hit her vacation-style peak during the summer of 1997. By this point, she was working closely with iconic designers like Jacques Azagury and Gianni Versace as she headed out on several Mediterranean getaways with Dodi Fayed. The princess had the flirty, free vibe of someone newly in love—notably different from her decorum-filled courtship with Charles—and her outfits reflected this impeccably. Short flashy dresses were the name of the game, as were colorful swimsuits and easygoing separates. Altogether, she was bolder than ever before, and the world has never forgotten it.

When the final season of The Crown came out in November 2023, we got to see faithful tributes to many of Diana’s best “summer 1997” style moments. Most notably, the show re-created the iconic yacht diving board photo to a T, from styling Elizabeth Debicki in the same style of blue one-piece to replicating the image’s eerie composure. The new version—which hit the internet shortly before the episode was released—got the internet talking almost instantly, just as the series’ take on the revenge dress did before it. While this certainly shows the creative team’s attention to detail, it also holds the power it does because there’s no one quite like Diana. Even with the sheer amount of style icons we have today, the people’s princess holds an unmatched, timeless status that remains a source of inspiration no matter what era or aesthetic is dominating the fashion circuit.

Why Princess Diana's Vacation Style Is Eternal

From effortless styling tricks to unexpected statements, Princess Diana’s travel outfits never failed to turn heads. She emanated the carefree, confident energy that we all want to have on vacation—even if we now know that things were much more complicated behind the scenes. Her swimwear and casual, off-duty looks are some of the most accessible parts of her style, and the fact that she consistently let her personality shine through made for memorable ensembles that transcend their era. No matter what trends emerge, we fully expect Diana’s sensibilities to remain a major source of travel wardrobe inspiration for many years to come.