The Most Fashionable Members Of The British Royal Family, Ranked By Timeless Appeal

The British royal family has rules and expectations when it comes to fashion. With big hats, long skirts, and opulent jewels, most of us don't dress like a member of this famous family on a regular basis. Many elements of what members of the monarchy wear are steeped in tradition, and that means we could imagine Queen Elizabeth II wearing them in her youth just as much as we could see Catherine, Princess of Wales, sporting them today. Still, one can't simply wear a stuffy ensemble straight out of 1955 and expect to make any best-dressed lists over 70 years later. So, the secret to impeccable royal dressing is being able to balance classic style with what feels fresh and interesting. Timelessness is key.

We've gathered together some of the British royal family's most fashionable figures. Yet, rather than ranking them from worst to best-dressed, we've focused on one detail that is uniquely important in royal fashion: timelessness. From members of the monarchy who have had great fashion moments but are more wrapped up in trends to those whose style is sure to stand the test of time, we've ranked these regal fashionistas from those with the least timeless taste to those who will surely live on as style icons forever. For more information about how we went about our ranking, stay tuned until the end.

Lady Louise Windsor may not be the most famous member of the royal family, but her stunning style transformation can't go unnoticed. Despite being young, Louise leans into the more classic, traditional elements of royal attire. Consequently, her wardrobe often feels retro and like something out of a storybook... a storybook or a decades-old Ralph Lauren catalogue. 

It's clear that Louise has very specific taste, and she knows how to execute it. It's hard to imagine Catherine, Princess of Wales, or Meghan Markle, Duchess of Sussex, donning many of the looks Louise has worn over the years, despite the fact that they've also had to dress appropriately for myriad royal events. This is because Louise seems to do more than just respect royal attire expectations; she really seems to love a vintage, traditional look. Louise doesn't find herself in the public eye as often as other royals. Yet, when we do see her out and about, we can always expect her to be dressed in something that her grandmother Queen Elizabeth II easily could have worn at her age.

Would Louise's wardrobe be appealing to most women her age today? Not so much. Unfortunately for Louise, "timeless" doesn't just mean that it would have worked decades ago; it also means it needs to work for decades to come, which isn't something she's mastered. Still, if you're into vintage, Lady Louise is a royal you'll want to watch!

For folks less familiar with the ins and outs of the British royal family, their first introduction to Princess Beatrice and Princess Eugenie was likely their now-infamous attire at Kate Middleton and William, Prince of Wales' wedding. With their wild headpieces and monochromatic looks, the sisters inspired plenty of jokes and memes. While the duo may not have been at their most fashionable at the 2011 nuptials, that doesn't mean that all of their ensembles have been bad. Far from it, in fact.

Beatrice has continued with her penchant for bold headpieces through the years. With hats, tailored coats, and frequent florals, she sometimes sticks with classic royal style. At the same time, she isn't afraid to embrace fashion trends. The mix of traditional and fresh makes for a uniquely preppy yet adventurous wardrobe that often allows her looks to stand out. Her blue floral toile dress at the Chelsea Flower Show in 2022, her plaid, belted dress at the 2023 Westminster Abbey Christmas service, and her stunning wedding day look in 2020 were among some of her many fabulous fashion moments over the years. Adding a dash of spice and eccentricity to an outfit can make it shine, but it does keep Beatrice's fashion a bit more trendy than truly timeless. 

Like her sister, Princess Beatrice, Princess Eugenie has worn some outfits that were so bad, we'll never forget. Over the years, though, she's had a stunning style transformation. She's grown into a more refined, sleek wardrobe than the louder, less focused one she had in her younger years. Her more developed taste has earned her fashion choices comparisons to Meghan Markle, Duchess of Sussex, thanks to her understated and simple yet perfectly clean and fitted looks. Even so, Beatrice's taste remains a bit too quirky and out-there to align entirely with Meghan's style.

When she was younger, Eugenie seemed more inclined to follow trends that came along than other royals, and this often didn't fit in particularly well with aristocratic events that she attended alongside her family. These days, she's found a way to marry her more out-there taste with classic aesthetics — sporting bright, bold color pairings with an a-line silhouette, embracing her love of fun headpieces in subtler ways, adding spice to simple ensembles with unique accessories, and more. Evidently, Eugenie has come a long way with her taste, but that doesn't mean we would praise any member of the monarchy for rocking these looks through the years. Overall, her wardrobe remains too niche to be as effortlessly classic as the style of royals ranked higher on this list, but we do love her edge!

Princess Charlotte may have ranked higher on the list if she were a bit older. As of now, she has yet to reach her teenage years, which means the jury is still out on her true personal style. Thus far, though, she has already had some amazing fashion moments. This is likely no real surprise, considering the fact that her mother, Kate Middleton, is a style icon herself. In reality, Charlotte's style doesn't venture too far from her mom's. 

Kids tend to want to embrace trends and experiment more with their clothes, rather than just matching their mom's classic ensembles. It's safe to guess that there have been a few occasions when Charlotte wanted to ditch her beige coat or oversized collar for something a bit more fun. Yet, when Charlotte does make a bit of a fashion statement, it manages to feel fresh and age-appropriate, while fitting in seamlessly with the rest of the family — like her Ray-Ban sunglasses at Wimbledon, for example. Time will tell how her taste will progress as she gets older. If what she's rocked so far is any indication, though, she's destined for fashion greatness.

Meghan Markle, Duchess of Sussex, may have bid farewell to working royal status, but she's still a member of the royal family. It just so happens that she also has some great taste when it comes to fashion. It's easy to see an outfit and think "that's so Meghan," which speaks to just how recognizable her signature style has become. She likes to look sleek, clean, and updated. Solid colors, fabrics with movement, and classic silhouettes are elements we see her incorporate into everyday 'fits and event attire alike. She loves to go for a monochrome moment, jeans with collared shirts, and tailored looks. 

Considering the fact that she left the world of the royals behind, it's not exactly surprising that Meghan hasn't leaned into that classic, vintage-inspired aesthetic that has become synonymous with curtseys and tiaras. Even so, Meghan's taste remains elegant and elevated in a way that always felt like it fit within the royal family while still feeling a bit more modern and fresh than what others are typically seen sporting.

Royal style just wouldn't be what it is today without Kate Middleton's influence. Her fashion sense is prime sophistication. She always follows the family rules with her attire while also subtly making it her own. She doesn't shy away from royally embracing some fashion trends when she finds one that suits her. Even then, though, she stays true to the core of royal fashion.

The Princess of Wales loves outfits with classic elements: a collar, a cinched-in waist, a blazer, a polka dot print. Paired with perfect tailoring and little desire to make bold fashion statements, she never fails to look perfectly put-together. One look at Kate through the years certainly indicates that she's always had interest in clothes. She had some iconic pre-royal fashion moments, too. Interestingly, those outfits did have a bit more uniqueness, personality, and interest than her wardrobe often does today, indicating that she has really settled into royal style and found a way to feel like her with what she wears, while also looking appropriate for her princess status.

When it comes to timeless style, Princess Diana is basically the blueprint. The world will never get tired of her most beloved looks — and for good reason. Diana changed royal fashion forever, and decades after her death, she remains one of history's most influential fashion icons. 

It's clear that Diana loved a little whimsy in her wardrobe. Yet, this managed to make her stand out, rather than look out of place. Her outfits showed how much she thoroughly enjoyed playing with fashion. She embraced trends of the '80s and '90s. Yet, from her oversized sweatshirts and bike shorts to her high-rise pants, even her 'fits that felt like they were of a very specific moment in time still feel cool today. Unlike some other members of the royal family, Diana was almost never spotted in an outfit that the average person would consider boring. Whether going casual or donning a tiara, her looks were all her own and often had a dash of playfulness amidst the preppiness.

Not every great outfit is one that will still look good a decade from now, and there's nothing wrong with that. Thanks to tradition, though, the royal family seems to value wardrobes that feel like they could stand the test of time. By the same token, not every one of Queen Elizabeth II's skirt suits was destined for a best-dressed list. The key to royal style is different from that of an A-list celeb or an influencer. For members of the monarchy, choosing a look that is as timeless as it is chic is basically the key to the perfect ensemble. This was precisely how our ranking came to be.

While we love some of Princess Beatrice's outfits over the years, for example, she hasn't quite mastered making her own taste feel ageless. On the flip side, Princess Diana was an expert at embracing trends and still making them feel like interesting fashion statements for decades to come. People are still attempting to replicate the revenge dress today. Does it get anymore timeless than that?