Princess Caroline Of Monaco's Best Fashion Moments

As both a member of the royal Grimaldi family of Monaco and the daughter of legendary Hollywood actress Grace Kelly, Princess Caroline Louise Marguerite has had to live up to some high standards. Yet, the royal has always managed to handle whatever was thrown her way with a sense of style and grace.

Over the years, the princess has overcome personal tragedies, including losing both her mother (per the Chicago Tribune) and her husband (per the Los Angeles Times) in tragic accidents. Since unexpectedly stepping into her mother's metaphorical shoes as the princess of Hanover (via Hello! magazine), this extraordinary woman has been committed to various philanthropic endeavors (via Prince's Palace of Monaco) — and she always looks good doing so, with Vogue naming her "one of Europe's most stylish royals."

Princess Caroline is also specifically known for her longtime love of Chanel and her years-long friendship with the fashion house's former head honcho, Karl Lagerfeld, per Tatler. Let's take a closer look at the royal's sense of style and explore some of her greatest fashion moments ever.

In the 1980s, as Princess Caroline of Monaco was thrown into her work leading various philanthropic organizations, she always managed to embody style and class with her fashion choices. In 1985, the princess was seen with her father, Prince Rainier III, at a squash tournament in Monaco wearing a stunning red-and-black plaid blazer adorned with gold detailing — which included chain accessories — with a pair of black dress pants, per Vogue. Her hair was worn down and accessorized with a simple headband.

It appears that the jacket is also one of Caroline's favorite pieces, as she's been publicly photographed wearing it more than once. In 1986, she was seen on a rainy day in London wearing the blazer, this time pairing it with a skirt (via Tatler). On her head, she wore a plaid hat that seemed to match the blazer perfectly. A thick gold cuff bracelet can be seen on her right hand, while her high-heeled pumps added a pop of color. She held a red Chanel handbag with a gold chain.

Of the look, Isabel Mundigo-Moore noted in an article for Who What Wear that the royal was likely to have drawn inspiration from the late Princess Diana's apparel.

Red dresses can be everything from sexy to regal to classic. On Monaco National Day in 2018, Princess Caroline of Monaco made her grand entrance in red, looking a bit of all three. She exuded royalty and elegance in an asymmetrical caped gown in bright red from Stella McCartney. She accessorized the gown with long white gloves, dangling earrings, black-and-gold cage sandals, and a red clutch, as noted by Harper's Bazaar.

In addition, the princess wore a red-and-white sash featuring the official colors of the country's flag, adorned with the Grand Cross of the Order of Saint Charles, a badge that featured multicolored jewels. The magazine further noted that the exact style of dress appeared to be sold out at the online couture retailer Net-A-Porter. (We found a similar dress by way of Neiman Marcus from designer Naeem Khan with a $4,995 price tag.)

While some of Princess Caroline's looks are more classic and subtle, others are bolder. In 2017, she was pictured at the Rose Ball alongside longtime friend Karl Lagerfeld wearing a Chanel creation that can best be described as dramatic.

Not everyone could pull off this look, but the princess did so with seemingly effortless confidence. She wore her hair down for the occasion, showing off a pair of dangly earrings. Per Town & Country, the black-and-white, full-length gown features a full collar neckline with a gold and emerald embellishment. The top of the dress is decorated with a black-and-white checkered design; a pink ribbon divides the top from the rest of the dress, which features a pattern of black swirls against a white background. Completing the dress are dramatic ruffled sleeves in white with black trim.

In an article from the Red Carpet Fashion Awards, writer Rachel Watkins described the princess' gown as "the epitome of elegance-meets-whimsicality." We couldn't have said it better ourselves.

More than once over the years, Princess Caroline of Monaco has wowed in pink. In 1980, per Vogue, she showed up to the Monaco Red Cross Ball alongside her family, looking sweet and stylish in a one-shouldered pink gown with a three-tiered skirt. She held a small bouquet of white flowers, with two gold bracelets on her left wrist. A close-up photo from StyleBistro shows off the rest of the princess' accessories that day: large diamond earrings and a turquoise bangle on her right hand.

Many years later, Caroline showed up at the 2018 Rose Ball in Monte Carlo, Monaco, in a similar dress alongside her daughter, Charlotte Casiraghi, and close friend, renowned Chanel designer Karl Lagerfeld. The Chanel dress, which was featured in the fashion house's spring 2018 couture show, has a mesh material at the top and on the ruffled sleeves (via Fashion Sizzle). The skirt of the dress boasts the same ruffles layered in three separate tiers. As Catherine Kallon of the Red Carpet Fashion Awards noted, the look was a departure from the riskier Chanel creation the princess had worn the year before.

In what may be Princess Caroline's most fashionable look yet, she wowed in Madrid in 2004 alongside her husband, Prince Ernst August of Hanover, as Town & Country noted (while the two are still legally married, they separated in 2009). 

Officially known as the Chanel 2004 Couture Tulle Sleeve Gown (per UFO No More), it is black from the waist down; from the waist up, it's all about the white bolero, which is adorned with ruffles, feathers, and a pink ribbon. In the center, she had placed a sparkling, jeweled brooch. The pink ribbon extends down the side of the gown, which includes a slit that shows off the black heels Princess Caroline wore for the occasion. Dangling from her ears were multicolored gemstone earrings.

Of the look, Who What Wear's Isabelle Mundigo-Moore described the bolero specifically as "a piece of art," which the princess "carried with so much grace."

Another work of art worn by Princess Caroline of Monaco appeared in 2019 at the Rose Ball in Monaco. Pictured alongside her brother, Prince Albert of Monaco, Caroline wore an off-the-shoulder gown in black, set off by an explosion of pink ruffles along the side (per Tatler). She held a bouquet of red, yellow, and pink flowers. The princess accessorized the bold yet feminine look with diamond earrings and a Van Cleef and Arpels three-string pearl necklace adorned with diamonds. According to Hello! Magazine, the necklace had belonged to the princess' late mother, Grace Kelly, and this was the first time Caroline had worn it.

This year's ball was particularly sentimental, as it was the first one since the death of the princess' close friend Karl Lagerfeld, with whom she had planned the event each year, noted the Evening Standard.

Another iconic look of Princess Caroline's is an all-white outfit accessorized with gold or pearl accessories — or even both.

In a photo roundup by Vogue, the princess is shown in a photo from 1975 wearing a white silk dress with a daring, plunging neckline. Around her neck, she wore a single strand of pearls, with flowers adorning her hair.

Fast-forward to the 1980s: In a photo from Chanel's fall/winter 1989 show, Caroline is seen in the front row next to Carole Bouquet, a French actress, in a white suit accessorized by layers of pearls around her neck. Pearl and gold bracelets are seen on her right wrist (per Town & Country).

In another all-white look from the 1980s, Caroline is seen wearing a white fitted blouse tucked into white pants. She dressed up her casual look with a gold belt and hoop earrings (via Who What Wear).

And, in 2021, Caroline was seen with her daughter in classic white, with her choker, bangle, and ring adding a pop of gold. The Telegraph described the outfit, a wrap-front jumpsuit from Halston (per New My Royals), as a "glamsuit."

Most of us love wearing our favorite jeans — and it turns out the royals are no different. Over the years, Princess Caroline has displayed a number of denim looks. In 1973, she was photographed walking with her family while decked out head to toe in denim, including a shearling jean jacket and matching flared jeans (per Vogue). A few years later, she was pictured on a trip to the coast wearing a casual but chic denim shirt (also via Vogue). In the photo above, taken many years later, the royal shows she still loves a basic denim shirt. 

Caroline was also pictured in Paris at Chanel's Fall 2013 Ready-to-Wear fashion show looking casually chic in a pair of dark jeans, a tweed blazer, and black boots, while carrying a black Chanel handbag with a gold chain, per Tatler. A closer look at her dark blue jeans, thanks to Hello! Magazine, shows a diamond pattern throughout.

While this next dress gives off some court jester vibes, we still love it. At a Royal Palace Christmas event in 2009, Princess Caroline wore a stunning gray Chanel dress from the fashion house's 2009 pre-fall collection. Even in gray, the princess managed to look festive, thanks to the dress' fun geometric design and ruffled neckline, sleeves, and hemline. The Royal Couturier later spotted the dress with tags listed on eBay for $2,800. According to the outlet, the original price of the dress is said to have been around $5,000.

In a rare 2014 interview, Caroline made a comment about her sense of style that seems quite appropriate in light of this look: "I was growing up in the hippie years and maybe there's a bit of that lingering on [laughs]. I think you have to have a sense of fun, even if it's not in perfect taste" (per AnOther).

And then we come to this look, quite possibly our favorite of all. At a 2013 gala benefiting Natalia Vodianova's The Naked Heart Foundation — an event that Princess Caroline attended along with her brother, Prince Albert, and his wife, Princess Charlene — she was the image of understated and refined elegance.

Featured in Town & Country's roundup of the princess' greatest style moments, her off-the-shoulder, white lace Chanel gown was trimmed in black and tied in a bow at the neckline. Her circular drop earrings (which she was also spotted wearing later in 2016 at the Longines Global Champions Tour of Monte Carlo) added a modern touch. Otherwise, the princess wore only dainty bracelets, letting the dress do all the talking, and held a most unusual clutch.

One comment posted to The Royal Couturier summed up the look well: "Caroline's dress embodied 'romance' to me. Perfect for the Love Ball!" We'd have to agree.

Princess Caroline has a habit of wearing looks straight off the runway. In 2006, she arrived at the Monaco Red Cross Ball alongside Prince Ernst August of Hanover in a white feathered gown with a long train, as noted by Tatler. The dress, which also features short ruffled sleeves and a thick bow at the neckline, is officially known as Chanel's HC Sequined Pussybow Feather-Trimmed Gown from its Spring/Summer Haute Couture collection of the same year, according to UFO No More.

The princess showed off a similar look in October 2019 when she attended the Secret Games, a 1920s speakeasy-themed event at the Casino de Monte-Carlo, with her family members, including her brother, Prince Albert. She wowed in a short-sleeved, feather-fringed gown first seen as part of Chanel's Spring/Summer 2014 Haute Couture collection (per Hola!). Caroline wore simple accessories with the statement dress.

We've already noted Princess Caroline's love of tiered dresses and gold accessories. In this look from 2004, she indulged in both. That May, Caroline was dressed to the nines to attend a gala held the night before the wedding of Crown Prince Frederik to Crown Princess Mary of Denmark. Her gold halter gown features tiers of shiny satin, each embellished with shimmering beads, per The Court Jeweller. Her matching gloves, clutch, shoes, and historic collection of jewelry completed the look.

According to The Court Jeweller, the princess wore some of her own jewelry paired with accessories belonging to the family of her husband, Prince Ernst August of Hanover. The diamond tiara she wore is known as the Hanoverian Floral Tiara, said to date as far back as the 19th century. It was designed to simulate the look of blossoms, leaves, and berries.

If you'd like a similar look for yourself, we spotted two from Mac Duggal that give off serious Princess Caroline vibes: the Beaded Sheath Gown and the One-Shoulder Ruffle Tiered Gown, both available at Nordstrom.

While many of Princess Caroline's outfits feature some degree of glamorous elements, this one was full-on glam. In a photo from a 1986 party in Los Angeles, the princess is dressed to the nines while surrounded by Hollywood legends, including Frank Sinatra, Roger Moore, and Gregory Peck (per Town & Country). 

Caroline's ensemble was certainly fit for Hollywood or European royalty — her black, low-cut halter gown features plenty of sparkling embellishments. Dangling from her ears were moon-shaped chandelier earrings with even more sparkle. Her makeup that evening was glam as well: red lipstick and smokey eye makeup, per StyleBistro. We don't think she could have selected a look more suited for the occasion.

While there's no way to recreate an iconic '80s look, we were able to find a couple of similar gorgeous gowns with a somewhat modernized look: the Lacey Cutout Sequin Halter Gown from Halston and the Embellished High Halter Mermaid Dress from Elizabeth K.

While Princess Caroline has had her share of tried-and-true looks, she also likes to change things up a bit and wear something not typical of her style. She did just that in 2015, when she attended an AIDS charity gala wearing a short, silver-and-white dress by Lanvin. While at first glance, the dress appears to have a watercolor effect, a closer look shows that it's actually not an abstract design at all but an image of a naked statue — hence its name, the Statue Print Dress (per UFO No More). It's a sleek and modern look that's also a bit "daring," as Town & Country described it.

Additionally, while we absolutely love her open-toed stilettos, the eye-catching sandals didn't take away from her overall look. The princess wore her hair down for the event while keeping it behind her ears to show off her dainty pearl earrings, a subtle nod to her penchant for classic pearls.

When choosing an outfit for a wedding or a night out, nothing beats a little black dress (LBD). Princess Caroline showed her love for the classic favorite when she donned a simple black dress to celebrate something else she loves: equestrian sports. As New My Royals noted, she was joined by her daughters, Charlotte Casiraghi (a talented equestrian herself) and Princess Alexandra of Hanover, as well as her son, Andrea Casiraghi, at the 2016 Longines Global Champions Tour of Monte Carlo. And, considering Caroline's love for Chanel, it's fitting that the LBD was made famous by none other than Coco Chanel (per Elle). 

Caroline's LBD, however, is not from Chanel; this time, she donned a dress from Lanvin known as the Bicolour Crepe Dress. The sleeveless sheath dress, which is made of 100% silk, is described as having a round collar (via UFO No More). What makes the dress so unique is its neckline, which gives the illusion of a plunging v-neck without actually showing skin. While the dress itself is simple and stunning, the princess' eye-catching white statement drop earrings and unique bracelet added the perfect complement.