5:15am PDT, Aug 3, 2021
Meghan Markle is many things: a royal, an activist, a wife, a mother, a changemaker and a woman with great style — most of the time. To mark her 40th birthday on Aug. 4, 2021, Wonderwall.com is taking a look back at some of her best and worst fashion moments over the years, from her days as an actress in America to her time as Prince Harry’s better half in Britain. First up? This regal red moment! Meghan arrived at the Mountbatten Festival of Music at the Royal Albert Hall in London in March 2020 in this elegant Safiyaa gown with a cape detail. She accessorized with matching red Stuart Weitzman pumps and a red bag by Manolo Blahnik.
Keep reading for more of the Duchess of Sussex’s best and worst looks…
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Meghan Markle rocked a strange color combo at the opening ceremony of the One Young World summit in London in October 2019. She arrived in an affordable frock from Canadian retailer Aritzia in a bold purple hue, but when it came time for shoes, she selected navy blue Manolo Blahniks — a surprising choice.
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A hint of things to come! A few months before she met future husband Prince Harry, Meghan Markle attended a World Vision event in Toronto in March 2016 wearing a sleeveless blush-hued dress in a flattering figure-hugging silhouette that we’d later see her in again and again once she became the Duchess of Sussex.
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Duchess Meghan wore a white dress in the same flattering silhouette (right after announcing her first pregnancy!) as she and Prince Harry stepped out in Sydney to kick off the first day of a royal tour of Australia in October 2018. She also scored sartorial points for wearing late mother-in-law Princess Diana’s diamond and gold butterfly earrings with the simple but pretty dress.
The internet was divided when Duchess Meghan attended the wedding of Prince Harry’s cousin Celia McCorquodale in June 2018 wearing this blue-and-white toile-print Oscar de la Renta dress. While some praised it as perfect for summer, others thought it was too big and baggy for the newlywed royal’s lithe frame. We’re on the fence, but when it comes to her wispy white fascinator — a $40 straw design from popular British retailer Marks & Spencer — that’s a hard pass.
A beauty in blue! Duchess Meghan rocked a look by Victoria Beckham while attending the Endeavour Fund Awards in London in March 2020. The short-sleeved midi-length dress paired perfectly with her navy blue Manolo Blahnik pumps.
Meghan Markle visited Canada House in London in January 2020 in this chic all-brown look — a Massimo Dutti sweater and silk midi-length skirt paired with velvet Jimmy Choo pumps.
A swing… and a miss. This early attempt by Meghan Markle — who briefly sported dark red hair — to deliver a stylish take on a blush-and-neutrals look, which she donned for the USA Network’s Upfronts presentation in New York City in May 2012, was clearly not her best.
Duchess Meghan arrived at the Commonwealth Day Service in London in March 2020 in this vibrant dress and cape combo from Emilia Wickstead. We loved the kelly green shade and the way she matched her William Chambers hat to the rest of the outfit. She added a darker green bag by Gabriela Hearst and tan pointy-toe pumps from Aquazzura to complete her look.
Next up? A vintage Meghan Markle look! She was starring on “Suits” when she visited the “Today” show in New York City in July 2016 (right around the time she met Harry!) to promote her USA show. We loved her striped shorts suit, which was a very on-trend look that summer.
Meghan Markle delivered another chic suit moment a year and a half later — this time in cropped black trousers and a matching blazer by Alexander McQueen — at the Endeavor Fund Awards in London in February 2018 (just a few months after announcing her engagement to Prince Harry). Though reports claimed the queen prefers female royals stick to skirts and dresses for these types of events, it made us think Meghan should suit up more often!
For the Endeavor Fund Awards in London a year later in February 2019, Duchess Meghan echoed elements of a chic suit in menswear-inspired separates by Givenchy — a crisp white button-down shirt with the sleeves rolled up tucked into an empire-waisted black skirt that covered her growing baby bump. We really liked the subtle call-back to the previous year’s vibe, but this time, the look just didn’t land.
If Meghan Markle was aiming for a sophisticated look when she hit the red carpet at the NBCUniversal Cable Entertainment Upfronts in New York City in May 2015, she only nailed it halfway. Her black pants were perfectly tailored and just the right length with her heels, but that tulle-wrapped tube top — despite its rich black velvet edging — was a major miss.
These black trousers from go-to brand Altuzarra were fine. But the belted dark blue scarf-style Oscar de la Renta top that Duchess Meghan wore with them during a visit to England’s Loughborough University in September 2018 had a peplum vibe that was just all wrong.
This peplum-style jacket, however, was a hit when paired with leather-look leggings and neutral heels for Meghan Markle’s appearance at AOL Build in New York City to promote “Suits” in March 2016. Months later, she told Good Housekeeping that when it comes to dressing in workwear, “Personally, I love cropped pants in vegan leather, a great fitted blazer and a button-down [shirt].”
This floral-print dress was a big win — and a look we think Meghan Markle could easily still wear today. She donned the fitted knee-length frock for the Tracy Reese show during Mercedes-Benz Fashion Week in New York City back in September 2013.
Her face nails how we feel about this dress: While we adored the strappy black Tamara Mellon heels Meghan Markle wore on her visit to the Commonwealth Youth Forum in London in April 2018, they couldn’t save this look: Her Altuzarra pinstriped midi-length dress was cute but way too baggy and shapeless.
Duchess Meghan scored a miss when she arrived at a Buckingham Palace garden party in May 2018 — her first public appearance following her royal wedding — in this bland and baggy blush-toned Goat Fashion dress featuring a sheer overlay and sleeves. Her pale pantyhose were the topic of much discussion too. Her disc-style hat by milliner Philip Treacy, however, was a solid choice.
This blush-colored look, on the other hand — a dress-and-blazer combo by Brandon Maxwell — was a huge win. A pregnant Duchess Meghan wore the coordinated separates to visit one of her new patronages, the National Theatre in London, in January 2019.
Though the print on the skirt and those thick-strapped heels might date this look that Meghan Markle wore to an NBCUniversal Winter TCA press event in Pasadena, California, in January 2014, it was still a great business-casual look that gave us an early hint about her penchant for a classic white button-down moment.
Some critics thought this was far too casual a look for her first public outing with her royal boyfriend, but we thought it was just right. Meghan Markle delivered another great white button-down moment, pairing the crisp shirt with ripped skinny jeans, flats and a fantastic oversized brown leather bag when she joined Prince Harry at his beloved Invictus Games in Toronto in September 2017.
Put this dressed-up denim look lands at the top of the miss pile! Meghan Markle was a briefcase girl on the gameshow “Deal or No Deal” when she wore bootcut jeans with a cropped black jacket and plenty of pearls on the red carpet at a National Kidney Foundation charity event in Marina del Rey, California, back in November 2006.
Meghan Markle looked out of this world in a metallic Misha Nonoo minidress at the 12th Annual CFDA/Vogue Fashion Fund Awards in New York City in November 2015.
This belted and box-pleated brown sheath with a metallic sheen and tapestry-inspired pattern would have been much better on Meghan Markle if only the cut of the bodice showed off her shoulders a little more. The actress wore this prim and proper dress as she left the “Today” show studios in New York City in August 2015.
This metallic look, however, was magic. Duchess Meghan topped a gold-and-silver jacquard minidress that she wore to a reception honoring father-in-law Prince Charles at Buckingham Palace in March 2019 with a long and crisp cream Amanda Wakeley coat.
If you can get past all the belly-cupping, it’s hard to deny how good a seven-months-pregnant Duchess Meghan looked in this smartly paired black-and-white print shift dress by Reiss topped with a black McQueen blazer. She wore the statement-making combo to an event in London in March 2019.
Same idea, radically different outcome: This look — a short white Herve Leger dress topped with a cropped black studded leather jacket — that actress Meghan Markle delivered during Mercedes-Benz Fashion Week in New York City in February 2014 was a solid miss!
Meghan Markle has long loved wearing blue. She’s also long loved a good fit-and-flare shirtdress. She combined both with this frock that she wore as she left the “Today” show studios in New York City in July 2016. We liked it but wished for a better fit. Still, she scores bonus points for those unexpected but great animal-print pumps.
This green Brandon Maxwell dress that Duchess Meghan wore in Sydney in October 2018 during her royal tour of Australia with Prince Harry was similar in style but a much better fit with sharper tailoring — in other words, a hit!
It’s another blue shirtdress-inspired frock, only better! This look featuring a belt and pockets in a similar silhouette fit Duchess Meghan like a glove. The Carolina Herrera denim dress that Meghan wore to the Sentebale ISPS Handa Polo Cup in July 2018 stands out as one of her best casual daytime looks to date.
This dark blue caped look by Stella McCartney was one of Meghan Markle’s crowning fashion moments. She donned the chic dress — and accessorized with an equally stellar Naeem Khan zodiac clutch — to join Prince Harry at a star-studded concert to celebrate Queen Elizabeth II’s 92nd birthday in April 2018.
They can’t all be winners! Duchess Meghan delivered a rare sartorial miss when she stepped out in this overly ruffled bespoke blue Jason Wu design for the 100 Days to Peace Gala concert in London in September 2018. Perhaps she chose the voluminous look to disguise her midsection, as she was newly pregnant but not ready to announce the happy news for another month.
This just might be our favorite of all Duchess Meghan’s maternity formalwear looks — Roland Mouret’s navy blue sequined Sarandon gown, which she accessorized with a gold bracelet once owned by Princess Diana and Stuart Weitzman’s classic heeled sandals. The Duchess of Sussex wore the beautiful curve-hugging dress when she and Prince Harry attended a Cirque du Soleil “Totem” performance to benefit Harry’s beloved Sentebale charity in January 2019.
Meghan Markle hit the red carpet at the 70th Annual Golden Globe Awards NBCUniversal party in Beverly Hills in January 2013 wearing this sparkling black cocktail dress that was part “Dynasty,” part future duchess.
Something sophisticated yet stylish in a great color? Duchess Meghan delivered in spades when she removed her cream cashmere Giorgio Armani coat to reveal a dark green silk blouse by the brand & Other Stories tucked into a deep green leather pencil skirt by Hugo Boss during her first joint visit with Prince Harry to the seat of their title, England’s Sussex county, in October 2018. This one’s definitely in the running for the royal’s best daytime on-duty look ever.
This green look just wasn’t up to snuff. Duchess Meghan wore the shapeless olive halter-style dress by Antonio Berardi for the Invictus Games closing ceremony in Sydney, Australia, in October 2018.
But this olive green look, with its body-conscious boat-neck cut, built-in belt and excellent coordinated accessories, was an instant hit. Duchess Meghan wore the Ralph Lauren dress and matching Stephen Jones hat with suede heels in the same hue to nephew Prince Louis’s christening in London in July 2018.
A month before her royal wedding, Meghan Markle combined two great pieces into one winning outfit when she threw a black Alexander McQueen blazer atop a pretty green pleated floral-patterned frock by Self-Portrait for an Invictus Games reception in London in April 2018.
This peacock green Jason Wu dress was great on its own, but those baggy sleeves and bodice were in desperate need of some alterations before newly pregnant Duchess Meghan wore it for her arrival at Nadi Airport in Fiji on day 10 of her royal tour Down Under with Prince Harry in October 2018. This one was just an unfortunate miss.
A killer combo! Duchess Meghan looked cool and confident in this green Erdem coat with black beaded appliques over top a matching maternity dress as she arrived at a Commonwealth Day Youth Event at Canada House in London in March 2019.
A coat can make or break an outfit. In this case, the sand-colored Mackage coat that Meghan Markle wore in Belfast, Northern Ireland, in March 2018 atop a cream Victoria Beckham cashmere sweater and green Greta Constantine skirt — along with those gorgeous bronze velvet Jimmy Choo pumps — turned this otherwise simple outfit into an undeniable hit.
This coat-topped look, however, was a major miss. Meghan Markle just didn’t need that giant fluffy Miu Miu monstrosity covering up the cute white top and pale blue high-waisted Wes Gordon skirt she wore to the Wes Gordon runway show during MADE Fashion Week in New York City in February 2015. Live and learn!
Another example of when a coat ruined a look? Look no further than newly pregnant Duchess Meghan’s decision to top her black side-button dress from Club Monaco with a loose tan trench by Martin Grant while in Melbourne, Australia, during her official royal tour Down Under with Prince Harry in October 2018. She made the same mistake, resulting in a messy look, when she topped her pretty pale Brandon Maxwell dress with a sloppily styled silk Burberry trench during an event in Auckland, New Zealand, nearly two weeks later.
Though this very brown ensemble that a newly engaged Meghan Markle wore to Christmas Day church services in Sandringham, England, in December 2017 left fashion fans divided, we’re among those who think it’s a chic hit. Meghan’s tan Sentaler coat served as both a neutral and complementary backdrop for her rich brown leather and suede accessories, which included a Philip Treacy hat, Stuart Weitzman boots and a Chloe bag.
We love it when a fashion risk pays off! A pregnant Duchess Meghan gave us another great coat moment — and simultaneously made a bold statement with an unexpected color combo — when she stepped out in a cherry red coat by Sentaler (that matched her Stuart Weitzman heels) atop a purple Aritzia dress during a visit to Birkenhead, England, with husband Prince Harry in January 2019.
A newly engaged Meghan Markle delivered a very stylish look when she arrived in Cardiff, Wales, with Prince Harry in January 2018 — a black Stella McCartney coat with a ribbon belt atop black skinny jeans by Welsh brand Hiut Denim and black velvet ankle boots by Tabitha Simmons. But once she took it off to reveal an unflattering Theory blazer-style Prince of Wales-check top with a wide bateau neckline underneath, we wanted her to put the coat back on!
This tea-length midnight-blue Dior dress featuring Duchess Meghan’s favorite bateau neckline fit her like a glove and couldn’t have been any more flattering. She wore it with a fascinator by Stephen Jones to join Prince Harry at the 100th Anniversary of the Royal Air Force in London in July 2018.
This boat neck dress, however, was an unfortunate miss. Though we loved the gunmetal gray color and the design — especially that scarf-like detail on the skirt — the fit was all wrong thanks to an avoidable fashion mistake: Duchess Meghan simply paired the wrong undergarments with the Roland Mouret dress she wore on the second day of her official visit to Ireland with Prince Harry in July 2018.
Duchess Meghan wore yet another look with a very wide neckline — this one went all the way off her shoulders — at her first Trooping the Colour in June 2018. Though she looked beautiful, she was criticized for showing too much skin in the blush pink Carolina Herrera ensemble. Her Philip Treacy hat game, however, was strong.
Just a few days after daring to bare her shoulders at Trooping the Colour, Duchess Meghan covered up in the chicest way possible — in a white Clare Waight Keller for Givenchy caped dress with a narrow black belt — during her first joint event with grandmother-in-law Queen Elizabeth II, which took place in Widnes, England in June 2018.
Even Givenchy can’t deliver every time. An example of a white dress/black belt look that missed the mark was this embroidered shirtdress from the design house that Duchess Meghan wore for her first Royal Ascot horse race in June 2018. Her hat, however, was another story entirely: The newlywed rightly drew raves for the bold black-and-white Philip Treacy design.
Paging nurse Meghan?! Though many loved the pillbox-inspired white hat that Duchess Meghan donned for the Commonwealth Day service at Westminster Abbey in London in March 2019 right before she began her first maternity leave — some even felt she was channeling style icon Jackie Kennedy Onassis with the accessory — we can’t help but think it vibed a little more Florence Nightingale. But we did love the Duchess of Sussex’s chain-print Victoria Beckham dress and matching coat.
It was modern. It was sleek. It was fresh. And it perfectly embodied Meghan Markle’s well-established style aesthetic as she walked down the aisle at St. George’s Chapel at Windsor Castle in May 2018 to marry her prince. Though the new Duchess of Sussex’s white silk cady haute couture wedding dress with a bateau neckline and three-quarter sleeves designed by Clare Waight Keller for Givenchy had its critics — “I would have done one more fitting,” pop star Katy Perry said — we think it was a gown for the ages.
Duchess Meghan stunned in bridal white again, though this time in a dress with a completely different silhouette than her wedding gown, as she and Prince Harry headed to their evening wedding reception in May 2018. Stella McCartney designed the bespoke halter-style creation crafted from silk crepe that showed off one of Meghan’s best assets — her shoulders. The new royal also scores sartorial points for the priceless new accessory she debuted as they sped off: a large blue aquamarine cocktail ring that previously belonged to her late mother-in-law, Princess Diana.
Let’s stick to white eveningwear for a moment. A newly pregnant Duchess Meghan took a page from her wedding night playbook and wore a glamorous white gown by Theia to dinner at the palace in Nuku’alofa, Tonga, during her royal tour Down Under in October 2018, once again accessorizing with Princess Diana’s aquamarine ring. A+ for taking a look that worked and reinventing it!
This formalwear look she wore a month later for her first Royal Variety Performance at the London Palladium in November 2018 was a big flop. We love a strong black-and-white color palette and can get behind sequins, but the overall design just looked far too matronly for stylish, sophisticated Duchess Meghan.
All is forgiven! Duchess Meghan and her growing baby bump stunned in a sleek one-shouldered black velvet gown by Clare Waight Keller for Givenchy when she presented the designer with an honor during the British Fashion Awards in London in December 2018.
We loved this gown at first, but as time has passed, we’ve changed our minds about the black-and-white confection by Oscar de la Renta featuring a laser-cut bird design that Duchess Meghan donned for the Australian Geographic Society Gala Awards in Sydney in October 2018 during her royal tour Down Under. Ultimately, it just feels like the voluminous gown is wearing her instead of the other way around.
When “Suits” star Meghan Markle attended the Elton John AIDS Foundation’s 13th Annual An Enduring Vision Benefit in New York City in October 2014, little did she know that just three and a half years later, the event’s host would be performing at her wedding reception. But thanks to her keen fashion sense, Meghan probably did know that the elegant dark teal Roland Mouret mermaid-style dress she wore that night would stand the test of time and still be a style win today.