Meghan Markle’s best fashion moments over the years

Though Meghan Markle is the master at current interpretations of classic royal style, Princess Diana was the first English royal to ascend to the status of fashion icon. In today’s era of social media, the 43-year-old American has redefined what it means to be a real princess. From her time as an actor on Suits to her current role as Duchess of Sussex, she has continuously pushed the boundaries of conventional style and crafted a fresh story that combines luxury refinement with simplicity. However, Meghan’s style progression extends beyond high-end designer brands; it also emphasises sustainability, repurposing classic pieces, and demonstrating that grace is always in style.

One of Meghan Markle’s best fashion moments occurred recently when she re-wore a breathtaking red Carolina Herrera gown — sending a clear message that true style is about quality, not quantity. Meghan’s wardrobe is filled with such iconic moments, each one reflecting her confidence, grace, and unique ability to balance royal protocol with modern, trendsetting looks. Whether she’s owning the red carpet or arriving at charity events, Meghan’s fashion speaks volumes about her individuality and ethos.

Let’s take a look at ten of Meghan Markle’s best fashion moments that truly encapsulate her evolution from Hollywood starlet to royal style icon, and giving us something to be inspired by everyday!

Meghan Markle’s best fashion moments over the years

1. The red Carolina Herrera Gown

The Duchess just delivered a major fashion moment at the 2024 Children’s Hospital Los Angeles Gala, reworking a look that’s already got the fashion world buzzing. Meghan stunned in the same red Carolina Herrera gown she first debuted at the 2021 Salute to Freedom Gala — but this time, she brought a fresh twist. Gone was the dramatic train, replaced with a more fitted column silhouette that featured a daring thigh-high slit and a plunging neck. The duchess knows how to remix a classic while keeping things chic and sustainable, and this was prime Meghan.

Her accessories were also on point — strappy red Aquazzura sandals that matched the gown perfectly, keeping the look monochromatic and effortlessly glam. The relaxed, beachy waves she sported added an extra layer of laid-back elegance. She kept her jewellery minimal with just a gold bangle, proving once again that less is always more when you’re working with a statement piece like this.

Meghan’s choice to re-wear such a bold look speaks volumes about her commitment to eco-friendly fashion — because let’s be real, nothing says sustainable chic like slaying the same iconic outfit twice. It’s modern, it’s smart, and it’s a style power move we can all get behind​.

2. The Givenchy wedding dress

This wedding dress, designed by Clare Waight Keller for Givenchy, stands out as one of Meghan Markle’s best fashion moments. The gown’s minimalist beauty lies in its sleek bateau neckline and three-quarter sleeves, constructed from double-bonded silk cady. This look ultimately showcased the actress’s refined taste and poignantly broke away from the traditional royal bridal styles.

But what truly elevated this ensemble was the incredible five-metre veil — a statement piece that told a story of unity. Hand-embroidered with flowers representing all 53 Commonwealth countries, along with personal touches like the California poppy and Kensington Palace’s wintersweet, the veil transformed Meghan’s walk down the aisle into a meaningful journey watched by millions around the world.

Of course, Meghan’s accessories were just as striking. She wore the Queen Mary Diamond Bandeau tiara, courtesy of Queen Elizabeth II, paired with Cartier diamond earrings and a bracelet. Her Givenchy silk duchess satin shoes completed the look. And let’s not forget the hidden “something blue” — a piece of blue fabric from the dress she wore on her first date with Harry, secretly sewn into the hem. This gown didn’t just make waves for its design; it perfectly encapsulated Meghan’s personal story and new royal role.

3. Stella McCartney reception gown

Ms. Meghan Markle wears a bespoke Stella McCartney high neck lily white gown in silk crepe to her Wedding evening Reception with Prince Harry in Windsor. #RoyalWedding pic.twitter.com/HE4sF7QAFd

— Stella McCartney (@StellaMcCartney) May 19, 2018

Meghan’s Stella McCartney reception look? Pure fashion perfection. It’s easily one of Meghan Markle’s best fashion moments and showed the world how she can nail both royal tradition and modern aesthetic. After her stunning Givenchy ceremony dress, the new bride made a serious style switch for the reception, stepping into a sleek, high-neck halter gown by Stella McCartney. The dress, crafted from lily-white silk crepe, was minimal yet completely stunning — showing that simplicity can pack a punch when done right.

And let’s not forget her accessories. Meghan added a deeply personal touch with Princess Diana’s aquamarine ring, a major style statement piece that blended royal history with her modern flair. With her hair pulled back into a chic updo and minimal jewellery, Meghan let the dress do all the talking. This was a total “less is more” moment — elegant, cool, and completely unforgettable. The look was modern, fresh, and effortlessly glamorous, proving that the Duchess of Sussex isn’t afraid to break the rules and do royal fashion her way. 

4. Safiyaa monochrome two-piece

At the 2018 Royal Variety Performance, the former actress owned the night in a jaw-dropping black-and-white Safiyaa gown. The halter neck dress had a sparkly, beaded white bodice that paired perfectly with the sleek black skirt. With her hair in a chic updo and minimal accessories, Meghan kept the vibe simple but stunning. The look was extra special since she was pregnant at the time, showing off her baby bump with that signature, modern-meets-regal style. Her pointed black heels and subtle jewellery completed the look, making this ensemble a standout at the event.

Meghan’s look was a perfect example of bringing contemporary edginess to the front instead of doing things the traditional way. The bold halter neck design broke away from typical royal fashion protocol, bringing in a more youthful, daring approach to maternity style. By keeping her accessories minimal — just a pair of sparkling stud earrings — she let the gown do the talking. This appearance was significant for Meghan, as it marked her first attendance at the Royal Variety Performance with Prince Harry, solidifying her place in royal events while staying true to her personal style.

5. Victoria Beckham turquoise dress

Meghan Markle made an unforgettable statement at the 2020 Endeavour Fund Awards, stepping out in a striking turquoise dress that instantly became one of her best fashion moments. Part of Victoria Beckham’s collection, the sleek, body-hugging midi dress featured a simple yet sophisticated silhouette with a zip-up back. Its vibrant shade was an absolute standout, especially against the rainy London weather, making Meghan literally shine as she and Prince Harry made one of their final public appearances before stepping back from royal duties.

Meghan paired the dress with navy suede Manolo Blahnik heels and a matching Stella McCartney ‘Lucia’ clutch. She finished the look with her hair slicked back into a sleek low ponytail. Her accessories were kept minimal but thoughtful — a Jessica McCormack rose gold bracelet and gold snake hoop earrings by London-based jeweller Roxanne First, adding just the right amount of sparkle to the fit.

6. Dior Couture at RAF Centenary

Meghan’s appearance at the 2018 RAF Centenary Service was a classic example of her nod to timeless pieces, adding another significant entry on our list of her best fashion moments. For this significant event at Westminster Abbey, Meghan chose a bespoke black Dior dress that channelled 1950s Audrey Hepburn. The structured A-line silhouette featured a fitted bodice with a bateau neckline, a signature of Meghan’s style, reminiscent of her Givenchy wedding dress. The cinched waist and full skirt added much-needed drama, and inevitably, a big dollop of vintage Hollywood glamour.

She paired the look with some refined accessories: a sleek black Stephen Jones fascinator with mesh detailing, a Dior clutch, and nude pumps that gave the monochromatic outfit a touch of softness. Her choice to wear black for the RAF Centenary was bold, as royals typically avoid all-black ensembles except for somber occasions; however, Meghan pulled it off effortlessly. Her updo was styled into a polished chignon, completing the final look.

7. Veronica Beard in Colombia

During her official visit to Colombia in August 2024, Markle made an elegant, yet practical fashion choice by stepping out in a sleek Veronica Beard ensemble. She wore a navy sleeveless Orlinda Vest paired with matching cropped trousers from the designer’s collection, striking the perfect balance between business chic and modern sophistication. With its impeccably tailored fit, the high-neck vest perfectly complemented the structured silhouette of the trousers, creating a sharp, polished look.

The outfit was further accessorised with black Manolo Blahnik heels and a quiet-luxury-approved white Loro Piana handbag. Loose waves and minimal gold jewellery kept the focus on the impeccable tailoring of her outfit, which was worn as Meghan and Prince Harry began their diplomatic engagements in Colombia, including meetings with government officials and ministers.

8. Johanna Ortiz for her Colombian engagements 

During her visit to Colombia in August 2024, Meghan Markle absolutely owned the fashion scene, serving three unforgettable looks by Colombian designer Johanna Ortiz that quickly became some of her best fashion moments. Each outfit was a perfect mix of effortless chic and tropical prints, giving us all a masterclass in how to mix local design with royal elegance.

First up, Meghan turned heads in a bold zebra-print dress by Johanna Ortiz. This dress was all about the drama, with a black-and-white pattern, thin straps, and a playful cutout at the waist. The thigh-high slit gave it that flirty edge, perfect for the warm Colombian weather. She paired it with oversized black sunglasses, gold bangles, and sleek black sandals, keeping the look glam yet totally relaxed.

Next, Meghan kept the fashion game strong with a black-and-white striped Johanna Ortiz set. With its breezy silhouette and strapless top, this two-piece screamed laid-back summer vibes while still looking super polished. Meghan leveled up the look with a chic wide-brimmed hat, a cream Cuyana crossbody bag, and brown sandals — basically a perfect vacay look, but with that royal twist.

Lastly, Meghan wowed in another Johanna Ortiz creation — a woven midi dress with intricate red-and-cream detailing. The sleeveless dress featured a classy slit, perfect for those tropical walks while still staying effortlessly chic. She kept the accessories minimal with gold jewellery and strappy sandals, making this look the ideal balance between sophisticated and easy-going. These looks were more than just stunning — they showed Meghan’s ability to mix high fashion with cultural appreciation, once again proving her mettle as a global style icon​

9. Valentino shift dress at Global Citizen Live 

At the 2021 Global Citizen Live Festival in New York’s Central Park, Meghan Markle turned heads in a crisp, white Valentino shift dress. The mini dress featured intricate floral embroidery that added texture and detail to the otherwise minimalist silhouette. Simple, yet striking, the look perfectly suited the event’s message of global unity and action. Meghan paired the dress with black Gianvito Rossi heels and styled her hair in loose waves for a relaxed, yet elegant vibe. Her choice of minimal jewellery and a sleek updo allowed the embroidered detailing on the dress to stand out, making it one of her most memorable public appearances in New York.

10. Martin Grant dress in Cape Town

During Meghan and Harry’s royal tour of Africa, the couple attended a reception for the youth and civil society leaders at the British High Commissioner’s residence in Cape Town. For the event, Meghan stepped out in a Martin Grant creation, a flowy, green-and-white striped dress that radiated both comfort and elegance. The flattering cut and cinched waist made the look effortlessly chic, perfect for a warm day in South Africa. She paired the dress with tan Castañer espadrilles and a delicate necklace, keeping her accessories light and summery.

(Main Image: Emmanuel Osodi and Eric Charbonneau via Archewell Foundation/Getty Images, Featured Image: Matt Winkelmeyer/Getty Images) 

This article was first published in Prestige Singapore