Royal Fashion: Maternity Style Moments Ranked

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31. Best: Princess Diana, March 1982

Princess Diana was spotted in Huddersfield on March 22, 1982, during her first pregnancy with Prince William. For the appearance, she wore a gorgeous magenta coat with a soft wool texture to it. We love how chic this statement coat looks and how flattering the straight cut style of the jacket looks with her budding baby bump.

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30. Worst: February 25, 2019

The Duchess of Sussex stepped out for a casual appearance on February 25 while visiting Morocco. Meghan opted for a simple striped long sleeve, black jeans and a pair of mid-calf boots. While it’s refreshing to see Markle in a casual look rather than her typical sophisticated dresses and suits, we couldn’t help but feel a little underwhelmed by this look. The pants looked a little messy tucked into the boots and didn’t quite fit her properly, and the entire look felt quite lackluster.

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29. Best: Kate Middleton, March 2015

Kate Middleton typically opts for solid colors, clean lines and structured pieces, which is why this leopard print dress definitely made quite the impression! During this 2015 public appearance, Middleton wore a shift style dress that featured a black and white animal print, long sleeves and hit her mid-thigh. To add sophistication to the look, Middleton slicked her hair into a polished ponytail which showed off her dainty pearl earrings perfectly. The print was bold enough to make a statement but she styled it in the classiest way possible.

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28. Worst: Princess Diana, June 1982

Diana was spotted again in June even closer to her due date for an appearance on the balcony of Buckingham Palace at the Trooping of the Colour ceremony. For the event, she wore a dark green dress with a matching hat. While we actually don’t mind this color on its own, it definitely wasn’t the best choice of color while standing beside men in red! The combination of the green and red clashed and the dark shade of green felt quite heavy for an early summer event.

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27. Best: Meghan Markle, November 2018

The expecting Duchess stepped out in late November 2018 wearing an absolutely gorgeous monochrome ensemble in a rich shade of burgundy. Markle’s shift dress featured a polished peter pan collar that she layered with a coordinating wool jacket on top. She opted for black tights and booties as accessories and pulled her hair into a low updo to complete the ensemble.

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26. Worst: Kate Middleton, January 2018

Kate Middleton stepped out in January 2018 while visiting Stockholm, Sweden wearing a blue velvet dress with a dramatic pattern on it. The look definitely received mixed reviews from fashion critics, and we’d have to agree that it isn’t a favorite. The heavy velvet and chaotic pattern felt quite overwhelming, especially for a maternity look!

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25. Best: Princess Diana, March 1984

Diana absolutely dazzled when she stepped out during the early stages of her pregnancy with Prince Harry wearing this drop-waist pale pink gown. From the sleek shape to the subtle glittering texture to the lovely shade of pink, this look totally stole the show on the red carpet.

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24. Worst: Meghan Markle, October 2018

Meghan Markle turned quite a few heads in one of her appearances on the 2018 Australia/New Zealand tour where she wore a royal blue sweater and skirt combo. While we love the pleated midi skirt and the contrasting pops of light blue, we’re not sure that the mom-to-be realized the skirt was completely sheer in the daylight! The look bared all from the waist down and we’re quite certain the Queen would not have been a fan of a look this revealing on a Duchess.

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23. Best: Kate Middleton, April 2013

Kate Middleton absolutely dazzled at the 2013 National Portrait Gala where she stepped out wearing this icy blue empire waist dress. The shape of this dress was super flattering on the expectant Duchess and the glitter texture really brought a glamour factor. She pulled her hair into a loose half-up style and accessorized with simple drop-style earrings.

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22. Worst: Meghan Markle, October 2018

For their second day in Fiji, Meghan and Harry both stepped out wearing flowery, boho numbers. While it’s rare to see Markle in a print, we can’t say this is one of our favorite styles on her! The shape of the dress itself isn’t too bad, but the bold print in combination with the pom-pom detailing at the waist came across a little tacky.

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21. Best: Princess Diana, June 1982

Diana stepped out again in June 1982 to attend a polo event at Windsor Great Park. She was photographed here with Prince Charles looking very pregnant in this silky pale pink dress. We love this chic, summery color on her and the choker detail really added a trendy element to her look.

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20. Worst: Kate Middleton, January 2018

When we first saw Kate Middleton’s red houndstooth Catherine Walker coat, we were actually huge fans! The ’60s-inspired look is undeniably different than anything we’ve previously seen her wear and it channeled some serious Princess Diana and Jackie O vibes. Unfortunately, her choice of burgundy accessories was a huge downfall for Middleton and the colors absolutely clashed. The orange-red color of the coat looked quite awkward with the maroon tones of the accessories and we truly wish she would have opted for nude or black instead to allow the coat to shine!

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19. Best: Meghan Markle, December 2018

Meghan Markle and Prince Harry were one of the sharpest dressed couples at the Christmas Day church service in 2018. The pregnant Duchess revealed her small budding bump in a midi-length knit navy dress. She paired the look with a matching navy overcoat, scrunchy leather boots and a formal fascinator on her head. The navy monochrome look was pure fabulousness!

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18. Worst: Princess Diana, April 1982

Pink seems to be the color of choice for Diana during her pregnancies, which seems funny considering she had two boys! This look she wore in April 1982 while pregnant with Prince William for a visit to Liverpool. For the appearance, she wore a bright magenta coat with a matching hat. This look was simply a little too frilly for us from the oversized ruffles on the shoulders of the coat to the bow on her hat and lacked the classic Diana elegance.

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17. Best: Kate Middleton, February 2018

Kate Middleton absolutely dazzled at the 2018 BAFTA Awards where she stepped out showing off her budding baby bump in an empire waist emerald number. We absolutely love how elegant the subtle bateau neckline of this dress looks. For added sparkle, the Duchess topped her look with an emerald jewelry suite.

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16. Worst: Meghan Markle, February 2019

We weren’t the biggest fans of this conservative look worn by Markle on the second day of their Royal tour of Morocco. The dress seemed to drown her in fabrics and felt a little outdated in terms of maternity fashion. The color also wasn’t the most flattering and seemed to wash her out.

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15. Best: Princess Diana, June 1982

We absolutely love this bubblegum pink maternity look that Princess Diana wore in June 1982, which was the same month William was born. The look was super effortless feeling with the undone buttons and rolled up sleeves, but still sophisticated and breezy for a summer afternoon.

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14. Worst: Kate Middleton, January 2018

We have to admit we weren’t the biggest fans of this cape number that Kate Middleton wore in January 2018 while visiting Sweden. The entire look seemed to feature an excess of fabric from the high neckline to the sheer cape to the floor-skimming length, which made it feel a little overly matronly and outdated.

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13. Best: Meghan Markle, March 2019

Meghan opted for a stunning Victoria Beckham dress on 2019 Commonwealth Day that consisted of a bold, chain pattern. To channel a little tradition, Meghan accessorized with a mod-inspired circular pillbox hat, which was an iconic Jackie O look for many years. For a pop of color, Meghan topped the crisp white ensemble with olive-colored pumps and a matching olive clutch.

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12. Worst: Princess Diana, June 1982

Diana stepped out in June 1982 wearing the same green polka dotted maternity dress she would wear to reveal William to the world a few weeks later. While this dress has likely become one of Diana’s most iconic and memorable fashion moments, we can’t say that it’s a favorite either. The pussy-bow detailing and awkward sleeves made this look appear a little stuffy.

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11. Best: Kate Middleton, March 2015

The expecting Kate Middleton was pretty in pink for the Queen’s birthday parade back in March 2015. This soft pastel color looked so gorgeous on her and the shift-style shape was flattering and strategic for a baby bump.

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10. Worst: Meghan Markle, January 2019

We have to admit that we weren’t the biggest fans of this bold colorful look worn by Markle in mid-January during a visit to Birkenhead. The combination of red and purple totally clashed and the entire look came as quite the shock from the neutral-favoring Duchess.

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9. Best: Princess Diana, June 1984

A few years later when Diana became pregnant with Prince Harry, she returned to her beloved pink maternity fashion despite having yet another son. In June 1984 she was showing slightly, but still able to conceal her bump with the help of a flowy dress and oversized cardigan. We absolutely love the chic feel of this fluffy sweater paired with an elegant midi length dress and kitten heels.

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8. Worst: Kate Middleton, January 2018

Kate Middleton rarely has a fashion misstep and consistently steps out looking head to toe fabulous, but we were quite disappointed to see her step out in this yellow floral Erdem number back in January 2018. The look seemed to drown her body in heavy silk and patterns. The ruffle around the ankle was confusing and didn’t seem to flow with the dress. Despite this, we love her elegant updo, but simply wish she had opted for something a little less distracting!

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7. Best: Meghan Markle, March 2019

In early March, the expecting mother-to-be opted for a striking gold dress which she topped with one of her favorite white coats by Amanda Wakeley. The golden number hit her just above the knee and featured an absolutely gorgeous cream and gold brocade pattern that gave off a metallic sheen. The shift style shape of this dress really flattered the Duchess’ budding baby bump and the golden tones made her appear even more glowing than she already is!

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6. Worst: Princess Diana, September 1982

In 1982 Diana stepped out to attend the wedding of her former flatmate Carolyn Pride in Chelsea, London. For the occasion, the pregnant Princess opted for a loose-fitting magenta dress with white detailing along the front. While it’s understandable to opt for something loose and breezy while pregnant, this dress was simply ill-fitting, which was unfortunate. Luckily, the bright fuschia color looked beautiful on her which compensated for the shape.

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5. Best: Kate Middleton, April 2013

This fashionable royal rocked polka dots in the most polished way possible back during her 2015 pregnancy! She paired the black and white spotted dress with a classy cropped cardigan and a pair of simple black pumps. Rather than look juvenile or immature, the print actually looked quite sophisticated and elegant, especially when paired with her voluminous waves and dainty diamond earrings.

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4. Worst: Meghan Markle, February 2019

Meghan recently stepped out in Morocco wearing a floor-length patterned dress that we weren’t the biggest fans of. The double-tiered ruffled sleeves overwhelmed her figure, especially when paired with the sweeping skirt that had no shape. We wish this look had cinched in or had an empire waist for a more updated version of maternity fashion.

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3. Best: Princess Diana, May 1984

Princess Diana looked super elegant and feminine when she stepped out in May 1984 while pregnant with Prince Harry wearing this Victorian-inspired lace gown. The subtle glitter laced throughout and the dainty button detailing along the sleeves made this a truly remarkable fashion moment, especially when topped with a sparkling crown!

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2. Worst: Kate Middleton, October 2017

Back in 2017 when it was announced that Kate Middleton was pregnant with her third child, many fans were on edge waiting for the first look the Duchess would wear to reveal her bump to the public. The first signs of her baby bump were clear when she wore this light blue dress in October 2017. As excited as we were about the new Royal baby, we, unfortunately, can’t say the same for this dress. The full lace look felt quite conservative and we weren’t fans of the unflattering sleeve detailing.

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1. Best: Meghan Markle, February 2019

The Duchess of Sussex put her own personal twist on winter whites when she stepped out in late February wearing a full white ensemble for a visit to the Natural History Museum in London to attend a gala performance. To jazz up the simple look, Markle accessorized with olive green pumps and a coordinating clutch, which brought a lovely and fashion-forward pop of color.

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Olivia Di Pede

Olivia loves all things fashion, beauty, and entertainment. In her free time, she can be found taking yoga classes, reading thriller novels, and styling outfits on Instagram.