Women of the Royal family have a certain standard they must abide by when it comes to fashion. The Queen has a clear etiquette list of dos and don’ts when it comes to dressing modestly, but that’s not to say that Kate, Meghan and Diana didn’t break the rules every once in a while. These Royal women are known for their tendency to break the boundaries and often this has resulted in stepping out in a risky outfit that the Queen might not necessarily approve of. Follow along for the riskiest looks worn by Kate, Meghan, and Diana:
Update: This article references Queen Elizabeth. Sadly, she passed on September 8, 2022 at the age of 96. She was the UK’s longest-serving monarch after reigning for 70 years.
47. Duchess Kate: Wide Leg Trousers
Wide leg trousers and culottes are a modern trend and something we’ve seen Meghan Markle wear on multiple occasions. Kate Middleton, however, tends to be more classic with her style, which is why seeing her step out in wide leg trousers was quite a surprise. Since this trend is quite modern and stylish, it’s likely the Queen would have preferred to see Kate step out in a tea dress or more timeless slim fit trousers.
46. Princess Diana: Wore necklace as a tiara
Diana loved to style her clothes in new and interesting ways and this look from a gala in Australia is the perfect example of that! The sparkling headpiece Diana wore was actually a necklace that was gifted to her by the Queen. It was remodeled for Queen Mary, then inherited by Queen Elizabeth in 1953, who chose to pass it down to Diana as a wedding gift. We’re quite certain this isn’t the way the Queen had in mind for Diana to style the piece, but we love her unique take on the traditional emerald necklace!
45. Meghan Markle: Pantsuit
One of the Queen’s preferences for the Duchesses is that they opt for skirts and dresses over trousers when it comes to public engagements. Meghan Markle, however, being the feminist and fashionista she is, has overlooked this rule multiple times throughout her royal reign. A trouser set can be just as sophisticated and elegant as a dress, and we’re glad that Markle realizes this as well despite the Queen’s opinion!
44. Duchess Kate: Low Rise Jeans
Low rise jeans were a huge trend in the early 2000s, which is around the time Kate Middleton and Prince William began dating. She is photographed here in her college days at St. Andrews looking just about as casual as we’ve ever seen her. A cami tank top, jeans slung around her hips and a tousled updo. We’re certain the Queen would not love seeing the future Duchess walking in public looking so casual!
43. Princess Diana: Wedding Look
Princess Diana’s wedding dress was certainly a product of its time. The ’80s were huge on extravagant, over the top wedding gowns, which is exactly what Princess Diana’s was with the oversized sleeves and voluminous skirt. While it’s true that the Queen must approve the Royal wedding gown before it is debuted, we imagine she might have had mixed opinions about the grandiosity of Diana’s look considering the Queen’s own wedding gown was much more simple and sleek.
42. Meghan Markle: Leather Skirt
We’ve never seen a royal step out wearing an edgy leather outfit, until Meghan Markle that is! Royal fans, and certainly the Queen, were shocked when the Duchess of Sussex stepped out wearing this risky leather skirt in early October 2018. While the forest green look is undeniably edgy, the great thing about it is that the leather gives off a high-fashion, sleek feel while still remaining elegant and modest enough for a Royal.
41. Kate Middleton: Rainboots
While to the general public, rainboots are a practical and comfortable option on a rainy day, we can’t imagine the Queen feels the same way. Kate Middleton was spotted in 2012 at The Golden Metropolitan Polo Club wearing casual green rainboots that became her go-to pair throughout the years.
40. Princess Diana: Low Neckline
Low necklines and royalty rarely go hand-in-hand! The royal family is known for being quite modest and conservative in the fashion department, which is why we can’t imagine the Queen would have approved of some of Diana’s more lowcut numbers, like this look she wore to a Charity Dinner At The New York Hilton Hotel.
39. Meghan Markle: High Slit
On October 22, the Duke and Duchess of Sussex were spotted on a casual stroll in Australia. The duo looked comfy and casual for the Australian heat, but we’re not totally sure the Queen would have approved of Markle’s breezy Reformation dress. While we actually are really big fans of this striped linen number, it didn’t seem the most appropriate choice for a royal because of its dangerously high slit! The royals tend to favor modest, conservative hemlines, and this high-slit number most definitely does not fall in that category.
38. Kate Middleton: High Street Brands
The Queen is known for her extravagant wardrobe of designers in every shade of the rainbow. While Kate Middleton definitely loves a good designer piece, that doesn’t mean she strays away from high-street brands either. We’re quite certain the Queen would have something to say about the $50 J.Crew sweater Kate wore while visiting the Scout Association’s UK headquarters in Gilwell Park.
37. Princess Diana: Wedges
The Queen has publically expressed her dislike of wedge-style shoes, so we can almost guarantee she scoffed at this casual look worn by Princess Diana in July 1981. Not only did the casual look involve overalls, but it also showcased bright pink wedges peaking out from beneath her pants.
36. Meghan Markle: Sheer Skirt
For one of Meghan Markle’s last appearances on the Australian Royal tour, she stepped out wearing this royal blue outfit that definitely turned quite a few heads, but we’re not sure whether it was for the right reasons! Her dress was, unfortunately, completely see-through on the underside of the pleats. We’re not certain whether Markle was aware of how revealing the skirt was in the light, but one thing we do know is that the Queen most definitely wasn’t happy once these photos were released.
35. Kate Middleton: Non-Weighted Dress
The Queen is known for her fashion trick of having weights sewn into the hemline of her dresses. This is to avoid having any wardrobe malfunctions on a windy day and ensuring her dress stays put. Back in 2011 when Kate was still a newbie to the Royal family, it was clear she didn’t follow this rule and had her dress fly up on more than one occasion!
34. Princess Diana: Bike shorts
Bike shorts were one of Princess Diana’s go-to looks during her casual off-duty days in the ’90s. While we love seeing Diana in her comfortable, relaxed outfits, we’re not sure the Queen would say the same, especially for shorts this tiny and short!
33. Meghan Markle: Off-The-Shoulder Neckline
Royals are always quite modest with their necklines and it’s an unspoken rule from the Queen to cover up while making public appearances. Although Markle’s off-the-shoulder number isn’t overly revealing, it’s definitely a fresh take on royal style and something a little more daring. We love how she still looks polished and professional as a respectable public figure, but still incorporates trends and her own personal taste in her looks. The Queen, however, might have a different opinion on Meghan’s boundary-breaking fashion tastes like this cold-shoulder top!
32. Kate Middleton: Country Mishap
In 2012, Kate Middleton and Prince William visited the Solomon Islands while on an official Royal tour. It’s typically expected that the Royals dress to honor the country they are visiting by wearing local patterns and colors. In a major fashion flub, the Duchess accidentally wore a dress by the neighboring Cook Islands to an official Soloman Islands dinner. We’re quite certain the Queen would not have been happy with this mishap!
31. Princess Diana: Sheer Skirt
This photo of Princess Diana is one of the most iconic of all time from when she was first dating Prince Charles and working as a Kindergarten assistant. The sunlight in this photo made the skirt appear sheer which displayed a silhouette of her legs. We’re certain that once Diana married into the Royal family that the Queen took precautions to help Diana have a more suitable and less revealing Royal wardrobe.
30. Meghan Markle: Mismatched Earrings
Meghan Markle is quite untraditional when it comes to fashion, and especially when it comes to accessories. One of the most notable style moments that broke boundaries was when she stepped out wearing two mismatched earrings. Royals typically opt for minimalist jewelry that features dainty diamonds or pearls and a look like this is definitely trendy rather than timeless, which is a royal style standard we’re not used to. Although we appreciate Meghan breaking boundaries and staying true to her own personal style, we’re not sure the Queen would approve see this trend as appropriate during a royal outing.
29. Kate Middleton: Short shorts
Even Kate Middleton went through a party-phase it seems based on this snapshot from her past! The photo was taken back in September 2008 for an ’80s themed roller disco party she attended with a friend. Clearly, the look wasn’t something Middleton would wear on a regular basis out on the streets, but we’re quite certain the Queen would want these photos of the now-royal buried based on the somewhat scandalous attire she is wearing. For any other celebrity, a look like this wouldn’t be questioned, but for a soon-to-be royal, a look like this definitely put Middleton in the hot seat for scandal.
28. Princess Diana: Engagement Look
One of Princess Diana’s most controversial looks was actually the azure blue set that she wore to publicly announce her engagement to Prince Charles at Buckingham Palace. Allegedly Diana pulled the ensemble from the racks of Harrods department store last minute, which was a surprise to many! She supposedly attempted to visit the high-end boutique Belville Sassoon but was advised by the French sales assistant, who obviously didn’t recognize Diana at the time, to visit a more budget-friendly store. Once the mishap was realized, Diana was welcomed back to their boutique which initiated the beginning of a long-time fashion partnership.
27. Meghan Markle: Pants vs. Dresses
Meghan Markle definitely surprised the world when she stepped out wearing these wide leg pants for a public appearance. Previously it was expected for royal women to wear skirts and dresses for official outings, but Markle has often opted for tailored pants instead. We love that despite joining the royal family, Markle still continues to stay true to her personal style and clothing preferences. Although we appreciate this shift forward, we’re not entirely sure the Queen would approve of her style preferences breaking royal protocol!
26. Kate Middleton: Colored Denim
The Queen is clearly a fan of color, but only when it’s on a tailored suit or outerwear piece. These coral pink jeans that Kate Middleton wore in March 2012 would definitely be a look that the Queen would find slightly garish. The bright pop of color is, in our opinion, a nice touch during the warmer months to liven up an outfit; however, we’re quite certain the Queen would have preferred Kate to wear a colored jacket or purse rather than a pair of jeans.
25. Princess Diana: Oversized tailoring
One of Diana’s go-to styles was oversized blazers and tailoring. The Princess obviously had quite the penchant for style and predicting trends because nowadays these styles are seeping back into the mainstream decades later. At the time, however, a Princess wearing anything oversized or not perfectly fitted to her body was quite controversial and something that hadn’t been done before.
24. Meghan Markle: All Black
Queen Elizabeth is known for her bright, eccentric wardrobe and almost always steps out wearing a bold pop of color. The Duchess of Cambridge Kate Middleton has seemingly followed suit and tends to lean towards colorful pastels and bright pieces within her own wardrobe! Meghan Markle, however, has proved with her latest public appearances that she will continue to stay true to her own love of neutrals and black. We think she looks totally chic and minimalist with this head-to-toe black ensemble, but we’re not sure the Queen would say the same!
23. Kate Middleton: Baseball Cap
The Queen is definitely no newbie when it comes to hats, but only when it comes to traditional British fascinators. The ever-casual baseball cap is definitely not a look we’d see the Queen in anytime soon and we can presume she wouldn’t approve of her daughter-in-law stepping out in public wearing one either. We get the practicality of rocking a ball cap when sailing, but we’re not sure the Queen would view the royal style error in this light!
22. Princess Diana: Revenge Dress
One of Princess Diana’s most iconic outfits is undeniably this off-the-shoulder minidress which was dubbed the “revenge dress” since she stepped out in it just following Prince Charles’ televised confession of infidelity. The revealing, leggy number was the perfect choice for a power outfit and Diana definitely had all eyes on her for more reasons than just Charles’ affair that evening at the Serpentine Gallery benefit. The dress was more revealing than her previous royal looks, but with her newfound freedom came a newfound love for even bolder fashion.
21. Meghan Markle: Statement Jewelry
It’s rare to see the Duchess of Cambridge Kate Middleton wearing exaggerated costume jewelry of any sort. Instead, Kate often opts for dainty diamonds or pearls, which we presume will be a transition that Meghan Markle had to make when becoming a Royal figure. Based on her previous public appearances, Markle tends to lean towards an edgier wardrobe, so statement jewelry might have been a difficult trend for her to give up!
20. Kate Middleton: Slouchy Boots
During her pre-royal days, Kate Middleton definitely had a more casual take on style. Even then, however, she managed to look straight out of Ralph Lauren catalog with her cable knit sweater, polo t-shirt and crisp white mini skirt. The look definitely suits her, but we’re not convinced it’s suitable for a royal in waiting, especially when it comes to her slouchy boots! The Queen is quite strict with her 2-inch round toe heels, so we presume she expects the same of her family. The sloppy boots definitely wouldn’t have received the royal stamp of approval and are a look that Middleton officially retired after marrying into the royal family.
19. Princess Diana: No hat
It was often expected for British royals to wear hats and fascinators for public outings, but Diana didn’t always abide by this rule! According to British Vogue, Diana was very intentional with her clothing and thought about the perception each piece would give off. Hats, for example, she thought made her seem unapproachable and even explicitly stated, “You can’t cuddle a child in a hat.” Although she did wear hats on most formal occasions, for hospital visits or visiting children, she refused to abide by this royal fashion protocol.
18. Meghan Markle: Ripped Denim
Denim isn’t completely off the table with royals, and most notably, when Kate joined the family we noticed a subtle transition into more casual streetwear when appropriate. Kate, however, often opts for polished dark denim in a tailored skinny fit that comes across rather professional. Markle definitely has her own approach when it comes to denim and has been spotted on multiple occasions wearing distressed styles! Even on her first royal appearance with Prince Harry, the trendy star rocked faded jeans with slits on the knees and a stringy, raw hemline. Although we love this edgy, casual look on Markle, we’re not certain the Queen would say the same!
17. Kate Middleton: Strapless Neckline
It’s no surprise that the Queen preaches for royals to wear high, modest necklines while out in public, but we’re not entirely sure that Kate Middleton agrees with this practice! This particular velvet look Kate wore for the Sun Military Awards in 2011 definitely caused quite a stir at the time because of its figure-hugging shape and strapless neckline. The dress was definitely more suited for a celebrity than a royal figure, but nonetheless, we think she looked gorgeous. The dress made headlines for being inspired by her late mother-in-law Princess Diana.
16. Princess Diana: No gloves
Similar to her no hat policy, Diana refused the previous royal tradition to wear gloves for public outings! Instead, she opted to keep her hands bare to allow a personal touch and skin-to-skin contact with those she met. Previously, it was expected that royals were higher in the social hierarchy and should not be touched, but Diana changed these notions with her humble demeanor and down-to-earth way of royal life.
15. Meghan Markle: Dark Nail Polish
It’s not just distressed denim or cleavage that is out of the question with the Royals, but details as minimal as nail polish are also a factor that Markle must have been told to change! The ever-polished Kate Middleton has shockingly never been photographed wearing nail polish and Queen Elizabeth has maintained a soft pink manicure regime for over 30 years. Based on the beauty track record of her predecessors, we’re quite certain we won’t see Markle step out anytime soon with anything even close to black polish on her nails!
14. Kate Middleton: Sparkly Dress
Queen Elizabeth is undeniably a fan of bold fashion, but rather than texture or embellishment she often opts for a simple bright color. It’s an unspoken style rule that royals dress to shine when they make a public appearance, but it seems that Kate may have taken this a little too literally when she stepped out at the Tusk foundation gala dinner wearing this sparkly number. Her look involved head to toe glitter, which we think looks absolutely fabulous on her, yet we’re not sure the Queen would agree! The typically polished and prim Princess Kate definitely took on a more sultry and glam style for this particular evening.
13. Princess Diana: One-shoulder neckline
The royal family never typically opted for anything overly fashion-forward or revealing, until Princess Diana joined the family, that is! Diana loved fashion and took to trendy cuts and styles when it came to dresses, such as this one-shoulder neckline. Nothing like this had ever been worn by a royal before, and it was quite refreshing to see a royal choose something sparkling and on-trend rather than something rather dull and lackluster.
12. Meghan Markle: Handbag vs. Clutch
Another unspoken royal fashion rule dictated by the Queen is to always carry a clutch versus a handbag or tote. The seemingly small style choice actually has quite a large significance in terms of public appearances! The Queen and Duchess of Cambridge almost always wear a clutch, which they often grasp with two hands, to avoid shaking hands with people. Whether she was aware of this protocol or not is completely unknown, but at one of her first public appearances with Prince Harry, Markle instead opted for a burgundy and navy tote bag.
11. Kate Middleton: Tracksuit
Kate Middleton always looks refined, even when it comes to her casual wear. She typically opts for a pair of dark skinny jeans and a variation of a cashmere sweater; however, she recently stepped out wearing one of her most casual looks yet with a ski jacket and pair of side-stripe athletic pants. This look is undeniably one of the most relaxed we’ve seen from a royal, but even so, she still looks gorgeous! We just don’t think we’ll see the Queen step out wearing track pants anytime soon.
10. Princess Diana: Low Back
Diana was known for forging her own path when it came to fashion and many of her outfits broke traditional style rules that were expected of Royal women. One, in particular, is this crushed velvet dress she wore to meet ballet dancers at Saddlers Wells theatre. The look was a gorgeous burgundy color and featured an oversized bow on the back. The real standout with this look, however, is the super low back that we’re quite certain the Queen wouldn’t have approved.
9. Meghan Markle: Dramatic Smokey Eye
To go along with her edgy style, Meghan Markle is undeniably a huge fan of a gunmetal smoky eye! Prior to her royal linkage, Markle’s signature makeup look was light, glowy skin, a natural lip color, and a contrasting dark lid look. Royals such as Queen Elizabeth and Kate Middleton are huge fans of the minimalist, natural makeup look, similar to their nail color, so we’re quite certain a dramatic eye look like the smokey eye won’t get the royal stamp of approval for Markle anytime soon!
8. Kate Middleton: Sheer Cutouts
This look is admittedly not one of Middleton’s riskiest, but it was undeniably a little scandalous when it comes to royal standards. The white garment featured sheer cutouts in every direction covering the entire length of the dress. A look like this would definitely require a slip underneath and despite reaching down to her ankles, it was definitely quite risqué, especially with the off-the-shoulder neckline.
7. Princess Diana: Casual fashion
Diana gave a new meaning to casual fashion when she joined the royal family! Before her, it was rare to see a royal wearing anything remotely informal, but Diana’s down-to-earth personality definitely gave way to a more low key style uniform within the royal family. This particular outfit was definitely one of her most casual consisting of a reindeer-printed knit sweater layered on top of a turtleneck and loose-fitting corduroy pants.
6. Meghan Markle: Wearing Canadian Brands
It’s an unspoken protocol that the royals support local fashion brands based out of the UK! Both Queen Elizabeth and Kate Middleton helped to put multiple British brands on the map by rocking local garments on a regular basis and helping to get British fashion brands in the public eye. Meghan Markle, however, has proven that the majority of her wardrobe is Canadian-based and has no shame to rock pieces from the country in which she worked for many years.
5. Kate Middleton: Knee-Baring Hemline
Another one of the Queen’s biggest royal style protocols surrounds dress length and hemlines. Although Kate Middleton is typically quite cautious to wear modest tea dresses that reach past her knees, there have also been a few occasions where she let the rule slip and wore something a little more risqué and thigh-baring. This look, for example, definitely broke the Queen’s rules and showed a little more leg than acceptable for a royal.
4. Princess Diana: Flashy textures
Royals definitely want to stand out when they attend an event, but Diana took this to the next level with her textured, glittering outfits! She loved flashy sparkles and embellishment, and sometimes both. This particular look consisted of a sleek dress that was covered in head to toe pearls which she paired with a suit jacket that matched perfectly with the dress. One would never catch the Queen in this type of flashy textured look!
3. Meghan Markle: Messy Bun
The royal family is known for its polished and proper ways, especially when it comes to grooming. Kate Middleton never steps out without her shiny locks perfectly coiffed or her updos tucked into a sheer hairnet, which she most likely learned from her role model Queen Elizabeth. Markle, however, has proved that these prim and proper hairstyles are a royal tradition of the past and has stepped out on many occasions with her hair twisted into a loose, wispy bun with pieces left out to frame her face. The look is still undeniably elegant, but we’re not sure the Queen would see the style like this based on her own hairstyle track record!
2. Kate Middleton: Cowboy Hat
This western-inspired look is quite an obvious outfit that the Queen wouldn’t approve of. Kate Middleton and Prince William stepped out in 2011 to attend the Calgary Stampede and undeniably dressed the part from head to toe. Kate’s look consisted of a white western cowboy hat, an oversized bull belt and a pair of traditional cowboy boots. Although we can understand that this look was all in good fun to go with the theme of the event, we’re not convinced that the Queen would approve of these casual, commoner-level outfits.
1. Meghan Markle: No stockings
Avid royal fans were appalled when Meghan Markle stepped out to announce her engagement breaking one of the most important royal style rules — always wear stockings! Kate Middleton and Queen Elizabeth are both avid fans of a short tea dress, but they always ensure to keep their look discreet by pairing sheer stockings underneath. One could argue that this dressing method is a way of the past, and Meghan Markle seems to agree by the looks of her public appearances with Prince Harry! She’s trendy, boundary-breaking and will definitely bring modernity into the traditional royal family when it comes to fashion.