Meghan, Duchess of Sussex, has certainly been through the wringer since she married Prince Harry in 2018. 

The now mother of two left behind a successful career as an actor to become a senior member of the royal family — something that sounds great on paper, but the reality was quite different. 

Despite opting to bow out of royal life in 2020 and make an abrupt exit from the U.K., the Sussexes have remained firmly in the spotlight. 

Thanks to an explosive interview with Oprah Winfrey, a captivating memoir from Harry, and a Netflix distribution deal, Meghan and her husband have remained in the spotlight.

Despite not being a senior working royal anymore, Meghan still gets a lot of attention whenever she appears in public.

 Of course, one thing that always raises eyebrows is her own personal sense of style and how it has evolved over time. 

This isn’t unique to Meghan, either. Royal watchers have long since been invested in what different members of The Firm wear, whether it’s Catherine, Princess of Wales, or Queen Camilla. 

While Meghan Markle’s best fashion moments won’t ever be forgotten, she doesn’t always get it right. In fact, there have been plenty of times in which Meghan has been caught wearing outdated fashion trends — especially since leaving the royal family sphere. This is not the end of the world, of coure, but when you’re a cultural and historical icon, these details don’t go unnoticed. So, let’s take a look!

There was a time when skinny jeans were a key staple in any self-respecting fashionista’s wardrobe. This was a trend that largely dominated the 2010s. Whether you were into alternative styles or catwalk looks, they were the one item that everyone had. For a long time, it seemed like this was one trend that wouldn’t die — but then Gen Z grew up and told us that we were all delulu. In 2021, the New York Post ran an article with such a title: “Gen Z deems skinny jeans out of style: Here’s what you can wear instead.”

Skinny jeans were officially over, according to the youth of today, leaving all elder emos and sleek chic queens broken-hearted and red-faced. It’s true that mom jeans, boyfriend jeans, and even cargo pants have been rising in popularity in recent years, with ’70s flares even making a comeback. However, Meghan decided not to pay any attention to the rally against her beloved denim and continued to wear them well into the 2020s.

When attending the Invictus Games in 2022, Meghan could be seen wearing a pair of denim blue skinny jeans with pumps and a white blazer. While the duchess looked flawless, the skinny jeans may have lost her points with her Gen Z fans for being a tad too old school. 

Oversized tailoring

We all know that trends come and go quicker than the seasons change, but some seem do stick around longer than others. Some ’90s fashion trends have made a comeback, while others seem to have died a slow, painful death before they’ve even taken off the ground. We first saw oversized tailoring take hold in the ’80s, but in fall 2022, it hit the runway again. Baggy blazers and loose-fitting pants were all the rage, bringing with it a sort of edgy office-chic culture that we could get behind — at least in 2023.  Meghan, Duchess of Sussex, appeared to hop on this trend in 2024, but it seems she was too late

Meghan appeared on stage at SXSW for a panel celebrating International Women’s Day wearing a $2,000 silk outfit by Giuliva Heritage. The beige pinstripe shirt and skirt hung off her body, and while the look wasn’t totally unappealing, it wasn’t very of the moment, either. 

Stylist Stephanie Stimmler lambasted the oversized trend when talking to HuffPost, calling it out for the sheer wastage of fabric as well as the impracticality of it. According to her, “the nipped, cinched-waist blazer seen on the runway of Stella McCartney, Proenza Schouler, Versace, and Chanel, to name a few,” was starting to replace this look by the end of 2023

Nude tones

This one may be a little controversial. Nude or beige dresses have been popular for years, reaching their peak popularity in the 2010s. However, it’s a look that doesn’t seem to die, despite dividing many fashion pundits. In October 2023, The Guardian’s Anita Chaudhuri wrote an article titled, “Why is fashion now so boring, beige and banal?” a tongue-in-cheek musing on why fashion had suddenly become so simple and lackluster. Meghan, Duchess of Sussex, could be lumped into that category if her look for Variety’s Power of Women gala is anything to go by. 

The nude dress, part of Proenza Scholer’s Resort 2024 collection, cascaded down to the floor. The simpleness of it was one thing, but the color screamed dull. Even Meghan herself once confessed to wearing colors that wouldn’t attract attention when she was a senior working royal in order to avoid stealing the limelight from other members of the family. “To my understanding,” she explained in the Netflix docuseries “Harry & Meghan,” “You can’t ever wear the same color as Her Majesty, if there’s a group event. But then you also should never be wearing the same color as one of the other more senior members of the family.” Her fix, she said, was to always wear “muted tones.” 

Naturally, it seems like an odd choice that she would continue to wear the drab shade voluntarily, considering her change in circumstances!

The shorts suit

Meghan Markle has worn outfits that just weren’t that flattering, but this shorts suit number isn’t one of them. There’s no denying that the Duchess of Sussex looked beautiful at the Invictus Games in 2023, with her long flowing tresses and glowing skin all making for a chic and demure aesthetic. Nevertheless, Meghan would have been better off leaving this outfit — a simple black tank paired with J Crew linen shorts and matching oversized blazer – on the hanger.

If you Google the term “shorts suits,” you’ll find a plethora of results — but most of them hail back to the mid-2000s, well before Meghan was even on Prince Harry’s radar. Indeed, there is something a little off about seeing a duchess wearing something that is both formal and casual at the same time. Perhaps it would have translated a little better had Meghan worn it 10 years ago!

Aviator sunglasses

Sunglasses styles go in and out of fashion more frequently than some other accessories, and for good reason. After all, they’re a big part of a look, drawing attention to the face before the rest of the outfit even gets considered. Aviator sunglasses have largely stood the test of time, first becoming popular throughout the ’70s and ’80s. Like many famous faces, Meghan, Duchess of Sussex, has been known to don a pair from time to time. The problem? They aren’t the most fashionable shades in this day and age. While aviators had a great resurgence in 2017, they have since dropped off in popularity. So when Meghan donned her gold-framed shades at the Invictus Games in 2022, she was a few years too late.

In 2020, ’90s shades were reigning supreme and by 2024, retro sunglasses remained popular, albeit with a modern twist. According to Refinery29, colored lenses, sport shields (think: ski glasses without the slopes), small metal frames, chunky oversized sunglasses, ovals, and cat-eyes are all dominating the trends in 2024.

We would love to see the duchess take a risk and put the aviators in the drawer for a while so she can make best-dressed lists with her eyewear alone!

Halter-neck dresses

The Duchess of Sussex has been known to wear a halter-neck top or dress on more than one occasion, which is interesting as it doesn’t exactly fit the royal family dress code. This is a tricky trend, most notably because it comes in and out of favor more frequently than some other looks. At the 2023 Invictus Games reception at the Hilton Hotel in Dusseldorf, Germany, Meghan wore a black version that treads the line between formal and workwear. However, the last time that halters were en vogue was two years prior in 2021, meaning Meghan was a little behind when it came to peak popularity. Regardless, Meghan has always been drawn towards this trend. Whether it’s enjoyed by the masses at the time or not doesn’t seem to phase the duchess. 

In 2018, after she tied the knot with Prince Harry, she wore a stunning Stella McCartney halter dress to the reception. There was little chatter about the fact it was a halter back then, as a lot of people actually preferred the slender number to Meghan’s ceremony dress. 

It’s not clear why Meghan leans towards this style so much, but it seems to work for her, especially when participating in formal events that require something more business casual than whimsical. 

Midi dresses

Just a few short years ago, we couldn’t get enough of midi dresses. They were everywhere you looked — from the runway to the hallowed halls of high schools across the world. While they certainly make for a striking silhouette in some cases, it seems that this once-popular dress style is on its way out. In 2023, several outlets, including the Daily Mail, reported that British retailer John Lewis had dropped floral midi dresses from its collection because they had simply been around for too long. It’s true that a lot of public figures, including Meghan, long favored the style.

At the 2023 Invictus Games, Meghan was pictured merging two trends with her color-blocked midi dress to another Invictus Games. Though the garment may have looked relatively simple, it was by famed designer Carolina Herrera. This look wasn’t her most on-trend ensemble, and we have to admit that this particular look isn’t one of our favorites on the duchess as it swamps her figure, despite being pulled in at the waist. Thankfully, she has gone on to embrace better silhouettes.

Statement necklaces

Meghan Markle has been breaking the royal rules when it comes to fashion since exiting Britain in 2020. The Duchess of Sussex appears to be taking some control back and taking risks she previously wouldn’t have with her style choices. Typically, royal figureheads are expected to dress flawlessly and conservatively, which leaves little room for modern fashion trends. With that being said, Meghan seems to be a little out of touch at times. While appearing on stage at the Invictus Games opening ceremony the same year she and Prince Harry exited The Firm, Meghan wore an off-the-shoulder top and a Cartier statement necklace reportedly worth roughly $15,000. 

The royal family, including Meghan, are no strangers to wearing expensive jewels, but it’s usually for a lavish occasion like a coronation or a wedding. While this Cartier gem might be expensive, it’s giving statement necklace from the ’00s. If you lived through the 2000s, you’ll remember just how popular big, bold necklaces really were. No outfit was complete without one — whether it be oversized beads, multiple layers, or a chocker, not dissimilar to this style moment. 

These days, jewelry seems to have taken a more understated turn, with many favoring simple chains with a sweet pendant, or subtle earrings that offer just the right hint of glam. Meghan herself is usually a part of this movement, so to see her step out of bounds was both interesting and a little confusing. 

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Source: USA Today