Meghan Markle Outfits That Just Weren't That Flattering

When you're a member of the British royal family, or any royal family for that matter, getting your style right is of the utmost importance. You're not just a public figure; you're a style icon and a role model — at least, if you play your cards right. Meghan Markle hasn't had it easy since she married Prince Harry in 2018, and even though she stepped down from her royal duties in 2020, she continues to be watched like a hawk by the media. We still want to see what she's wearing; Meghan Markle's most risque looks since leaving the royal family have certainly turned heads.

With that being said, Meghan hasn't always got it right over the years. Though some of her outfits have been so on-point she stood to rival fellow royal fashionista Catherine, Princess of Wales, others have missed the mark. One such flop took place before she married into the royal family — and it continues to haunt her. "I was going to this event and there was this DVF lace dress with a zipper up the back, and it was so fitted, and had tea length sleeves," she told Glamour in 2017. "It was too tight, and too short, and my hair was too polished, and everything about it was trying too hard."

From her early days as an actor making a name for herself in Hollywood right up to the present day, here are some of Meghan's less-than-flattering looks that we won't be able to forget any time soon.  

There are times when a baggy outfit works well and fits the occasion to a T, even in formal settings. Unfortunately, Meghan Markle did not quite nail this casual aesthetic when she appeared at SXSW on International Women's Day in 2024. The mom of two appeared at the Austin event to speak as part of a panel called "Breaking Barriers, Shaping Narratives: How Women Lead On and Off the Screen." She sat alongside other big names in the entertainment industry, such as Katie Couric and Brooke Shields. 

Perhaps in a bid to appear both effortless and fashionable, Meghan opted for an outfit by Giuliva Heritage. The pinstripe champagne shirt was paired with a matching skirt. While it was a valiant effort to turn business casual on its head, something about the look didn't pay off. The overall effect was underwhelming, and the billowy set all but swamped her. On top of that, the loose-fitting ensemble appeared dull under the stage lights.

We will give Meghan her dues, though: It was nice to see her hair down in loose waves instead of in her signature bun, and the gold Bottega Veneta Knot earrings gave the outfit a much-needed bit of sparkle. It didn't quite take it from drab to fab, but they were a good choice of accessory. 

Of all of the things that went wrong at Prince Harry and Meghan Markle's wedding, her ill-fitting dress is up there with the best of them. Just about any bride will tell you how important their wedding gown is, and when you're about to marry into the royal family, there's a lot of pressure for it to be absolutely perfect. After all, the photos aren't just going to linger in an album. They will be seen by millions and become part of history. Catherine, Princess of Wales, absolutely nailed her gorgeous lace gown in 2011, so the world couldn't wait to see what Meghan, Duchess of Sussex, pulled out of the bag. Unfortunately, many were disappointed by her simple white Givenchy dress with three-quarter-length sleeves. 

Many felt that it was simply too plain for such a grand occasion, even if it did cost $100,000. The simplicity of the gown wasn't the only thing that ruffled pundits' feathers; there were questions about whether the dress had been properly fitted. Even one of Catherine's preferred royal stylists, Emilia Wickstead, told the Daily Mail, "If you choose a simple design, the fit should be perfect. Her wedding dress was quite loose." 

This sentiment was echoed by singer Katy Perry. When asked by Entertainment Tonight what she thought of Meghan's choice, the pop star said, "I would have done one more fitting. I'm never not going to tell the truth! One more fitting, but I love you."

Before she was Meghan, Duchess of Sussex, she was Meghan Markle, an actor who became a household name thanks to her work on the hit series "Suits." Meghan isn't the first Hollywood starlet to marry royalty (shout out to Grace Kelly), but she is the only one to do so in the modern age of the media. Because of her previous career, there are tons of photos of Meghan pre-Prince Harry that show her posing at red carpet events, parties, and more. Some of her looks are perfectly put together and well-executed, while others aren't quite so glamorous. In 2013, Meghan attended the Annual Charity Day, hosted by Cantor Fitzgerald and BGC at their office in New York City. 

Given the occasion, Meghan opted to keep it modest in a knee-length dress, but it's the bold pattern that we take issue with. The blue and yellow shapes and shiny material give this vibe a distinct office look, but one that even her "Suits" character Rachel Zane wouldn't wear to her 9 to 5. Yes, it was 2013, but when you consider that it was the year of some incredible trends like monochrome and suiting, it's difficult to see why Meghan went down this route. 

While GoFugYourself called it "cute," this particular dress doesn't totally land with us. It's simultaneously dated and futuristic while also kind of overwhelming to the eye. Needless to say, this doesn't appear in Meghan Markle's best fashion moments ever.

By 2019, Meghan Markle was officially a member of the royal squad. However, she was still relatively new to the whole operation in the grand scheme of things. Catherine, Princess of Wales, had almost a decade of royal style practice under her belt before she wed Prince William; Meghan and Prince Harry got married less than two years after they first started dating. Maybe it's this lack of experience that lulled Meghan into a false sense of fashion security when she chose this burgundy leather skirt and sweater combo. 

Meghan wore the outfit when she attended a roundtable discussion on gender equality with The Queen's Commonwealth Trust alongside Harry in Windsor. While not a total disaster, the sweater created a bulky silhouette when tucked into the tight leather skirt. What's more, Meghan's messy up-do would have been more fitting for a Hollywood luncheon. 

On paper, the idea of a monochromatic look would seem perfect for the event — after all, Queen Elizabeth II was known for wearing only one color at a time. However, the different shades of burgundy clashed, and all in all, the look seemed more fitting for a vampy soap opera character to wear over a duchess attending an important event. It may not be one of her worst looks, but it isn't her best, either.

Anyone who follows the British royal family calendar knows that Royal Ascot is one of the most important events of the year. The prestigious racehorse competition, which invites jockeys compete for trophies and prize money in different races, also happens to be a big fashion event for the royals. Catherine, Princess of Wales, for example, has pulled some incredible looks out of the bag over the years for the happy event, and she's not the only one. Princess Diana, of course, sported some of the royal family's best Royal Ascot looks ever. Alas, Meghan Markle hasn't been able to reach that high bar. 

Meghan attended the prestigious social event for the first time in 2018, alongside Prince Harry. As of this writing, it's the only time she's gone. While many Royal Ascot attendees tend to don charming prints, bold textures, fun silhouettes, and rich pastels, Harry's other half went with a far more subdued pick. Instead of a whimsical or colorful frock, Meghan wore a white button-down Givenchy shirtdress with a black belt. The long-sleeved number felt a little matronly as opposed to chic, especially when paired with a black and white hat and black clutch bag. Moreover, the handkerchief hemline was a bit meh.

Suffice it to say, Meghan's dress left many wanting more. Shortly after she made her Royal Ascot debut, New York Post declared that her royal style felt "frumpy."

Out of all of the royal events that take place every year, Trooping the Colour has to be one of the most prestigious. The celebration is an over-the-top display that Brits absolutely adore, not least because it's to honor the monarch's birthday. Trooping the Colour fashion has been an important part of the day for decades, with all eyes on the best-dressed royals of the day. In 2019, Meghan Markle and Prince Harry were still senior working royals and therefore, they appeared at the ceremony decked out in their finest. 

Meghan opted to wear yet another look by Givenchy for the occasion, this time a navy blue number by the fashion house's designer Clare Waight Keller. Unfortunately, the cut did nothing for the beautiful duchess, with the high neckline and angular sleeves broadening her shoulders. At some points throughout the day, she was also spotted in navy leather gloves. At first glance, they almost looked like disposable food prep gloves.

All in all, it was largely an underwhelming choice for a day that's literally dedicated to color. Other members of the family, including the late Queen Elizabeth II, have previously opted for something bright to commemorate the joyous day. That being said, Meghan reportedly made an effort to wear duller colors when she was a working royal so that she wouldn't upstage higher-ranking female royals. 

After Meghan Markle and Prince Harry made their abrupt exit from the U.K., many pundits wondered if they would ever attend a royal event again. Though they did step down from their senior duties in order to figure things out, that doesn't mean that they cut ties with the House of Windsor for good. Meghan, Duchess of Sussex, has always made a point of praising Queen Elizabeth II and even named her second child, Lilibet Mountbatten-Windsor, after her. Perhaps it was out of respect for her grandmother-in-law that Meghan chose to return to the U.K. to participate in a service of thanksgiving for the Platinum Jubilee Celebrations in 2022. 

Meghan was all smiles on the day, and while her outfit was not a total disaster, it could have been better. Meghan wore a Dior stone white trench coat with an oversized collar and three-quarter sleeves that appeared more tight than fitted. The coat dress was belted at the waist, and the look with a wide-brimmed Dior hat. The hat was worn at a jaunty angle to accommodate Meghan's trademark low bun, but when viewed from a certain angle (as seen above) Meghan's hair wasn't visible, creating a slightly peculiar effect. 

Regardless, the duchess appeared in good form. This was one of her final visits to the country ahead of Elizabeth's death.

Working royals have a number of duties, including trekking around the globe to meet with heads of state. Before Meghan, Duchess of Sussex, and Prince Harry parted ways with the royal family, they made a number of official visits to other countries. And during one of those visits, Meghan made a small, albeit very noticeable style mistake. While in New Zealand in 2018, the duchess wore a striking red dress... and forgot to remove the tag from the bottom of the skirt's hem.

It's a fashion faux pas that any public figure — or private citizen, for that matter — would cringe at. As Meghan walked down the steps arm in arm with her husband, the tag could be seen flapping in the wind next to her chic black pumps. The red floral dress from Self-Portrait may have fared better had it not been victim to this oversight, but as it happens, it made the headlines for all the wrong reasons. While many outlets noted that it was a relatable gaffe, there was no shortage of jokes about whether or not she planned to return the dress. 

As lovely as the dress was, it's no stretch to say that her ensemble was overshadowed by the small rectangle dangling from her hemline. Thankfully, Meghan seems to have learned from this transgression and been more vigilant with tag removal in the years that followed. 

In 2018, the best moments from Prince Harry and Meghan Markle's wedding were still fresh in the public consciousness. No one knew how things would play out over the next couple of years or how much the House of Windsor would be rocked. In the early days of their marriage, Harry and Meghan, Duchess of Sussex, were busy doing their duties and visiting other heads of state. They even hopped over to the Emerald Isle, where they schmoozed with the locals and met Ireland's leaders. While Meghan did have some style wins on that trip, including a stunning tailored black suit, she also had some losses, including this grey dress. 

The calf-length dress by Roland Mouret was made of crepe and featured a statement ruffle on the skirt. Alas, even with the asymmetrical hem, it lacked a wow factor. What's more, Meghan wore the wrong type of bra underneath the outfit: The duchess appeared to be wearing a strapless bra, which did not exactly work with the shape of the dress. Rather, it created a bunched-up, almost pinched effect. 

Of course, it wasn't long before the media noticed and published stories about the blunder. Furthermore, as The Sun pointed out, Meghan previously wore the same dress in a much more striking blue hue, which just goes to show how much color can impact an aesthetic. 

Tailoring is always important, even if you're wearing a shift dress, and while Meghan Markle has proven that she can do it well, she doesn't always completely nail it. In 2019, Meghan wore a striking purple dress to the One Young World Summit. There's no denying that the color looks regal and beautiful on her, but the shape of it left something to be desired. The long-sleeved, ankle-length number wasn't an expensive designer piece that was totally inaccessible to her fans, either, but by Babaton, which was on sale for as little as $50 at the time. 

It was very nearly a hit. Again, the rich purple hue of the dress was anything but drab, and the duchess was positively glowing.  However, had the dress been altered to fit Meghan's figure it would have been a perfect addition to the duchess' wardrobe. Alas, the silhouette was a bit too shapeless.

It wasn't the first time she wore it: Meghan was previously spotted donning the outfit while pregnant. Perhaps she bought it in a bigger size and after having the baby, didn't want to simply discard it. We have to admire the sustainability element here, but it doesn't stop us from wishing it'd been taken in just a bit before it was let out to play once more.