Princess Diana-Approved Trends That Are Making A Comeback

When fans and royal watchers reminisce about the dazzling Diana Spencer, many aspects come to mind. The late Princess of Wales' dedication to human rights efforts, the AIDS crisis, and advocating for the removal of landmines often tops the list, as does her public display of affection towards her sons, Prince William and Prince Harry (such PDA is relatively uncommon amongst members of the firm). Still, others might think about her tragic death and the life cut short that is still mourned to this day, while many may ponder what Diana would think about her sons' feud if she were alive today.

Diana encapsulated so many critical elements of royal life in her short time with us. Yet, one aspect of her public persona that many still recall as her most triumphant is her fashion sense. The late Princess of Wales not only dressed within the trends of the time but often set new ones in motion — from cowboy boots and jeans to bike shorts topped with baggy sweatshirts to dazzling evening wear, Diana's sense of style is still remarked as one of the most iconic displays of royal fashion. While the dearly departed princess hit the top trending lists more than two decades ago, her impact on the fashion scene is still very much felt today — these Diana-approved trends are even coming back.

Structured blazers

If there was one component of Diana Spencer's wardrobe that made its way onto the royal fashion scene on many occasions, it was the structured blazer. Such a menswear-inspired garment was a favorite of the princess's. She was spotted in detailed blazers while attending royal events, out and about with her sons, and making special appearances at high-profile events.

For instance, the oversized white blazer she chose to wear while attending the Cannes Film Festival in 1987 is a favorite of ours. The silhouette was sleek and sophisticated — but to tone down the structure of the blazer, Diana paired it with a full dress that billowed at the knees. The juxtaposition of the garments worked beautifully for the red carpet moment.

Still, other sightings of Diana wearing a blazer occurred at both royal events and casual outings. She chose a cream-colored blazer — with black piping detailing — and matching pencil skirt for a 1988 event at London's National Gallery, pairing the look with a simple black clutch. But, while attending the 1988 London marathon, Diana wore a pale yellow blazer over a graphic t-shirt. The oversized structure blazer was a favorite of the princess's, and a variety of options should be a staple in your wardrobe. Pair your structured blazer with a great pair of straight-leg jeans and boots for a fall-appropriate look, or throw a blazer over a casual dress to instantly elevate your look.

Coastal chic

Anyone familiar with the variety of aesthetics trending on TikTok knows that the coastal grandma look is all the rage. Sourcing inspiration from Nancy Meyers, Diane Keaton, and the glorious recipes of Ina Garten, the coastal grandma trend is all about embracing the more relaxed elements of life — adorned with a perfect white sweater, cream-colored jeans, and striped shirts to match. But, anyone who wants to embrace such an aesthetic should look no further than Diana Spencer, who made coastal chic very much a staple in her wardrobe.

A fan of the sailor-inspired look, Diana wore nautical-like garments on multiple occasions, proving that a touch of white against a sea of navy material was an option worth considering. Perhaps one of our favorite looks of hers came in the form of an oversized white sweater — adorned with a blue kerchief pattern — paired with a flowing white skirt. The unexpected silhouette was a very relaxed option for the princess and one that is easily recreated today.

Another nautical-inspired look worn by the princess came in the form of a stunning black suit dress that featured a white sailor collar, a black satin bow, and gold buttons. The look was a bit more understated than some of her other coastal chic looks and is a perfect outfit to replicate if you want to bring the aesthetic to a more dressed-up event. Diana was ahead of the trends.

Sporty styling

Of all the Diana Spencer-approved looks coming back, the cycling shorts and oversized sweatshirt look is perhaps the most popular. Diana, of course, looked stunning in evening wear and brought out all the stops when she wanted to. Still, her go-to gym look — often made up of a pair of bike shorts, white chunky '90s sneakers, and a fun, oversized sweatshirt — is easy to replicate and just as stylish today as it was when the late princess donned such a look.

Some of Diana's best pairings included her Harvard sweatshirt and black bike shorts, her Virgin Atlantic sweatshirt and orange bike shorts, and her white and black sneakers (with ankle socks, of course). The princess was often pictured wearing such outfits when she came to and from the gym, but given that streetwear and casual aesthetics are carrying us out of the pandemic-ridden world, replicating such a look is easy, comfortable, and Diana-approved.

It's no secret that the bike short look has had a comeback, and as noted by Express, Diana's look has received a spike in Google searches thanks to the trending outfit option. The term "bike shorts" has enjoyed a 250% spike in searches — meanwhile, the search term "princess diana 90s fashion" has seen a 100% increase. So, what are you waiting for? Grab some bike shorts, a cozy sweatshirt, some chunky dad sneakers, and a great pair of sunglasses — Diana would certainly give you her nod of approval.

Fun knitted sweaters

With the colder weather rolling in and fall in full swing, many of us are looking to revamp our sweater collection. If you're looking for a Diana Spencer-approved look to add to your wardrobe — but want to stay warm and cozy while doing so — turn your attention to her fun knitted sweaters that accounted for many of her best looks. As Vogue detailed, Diana wore a "grandma knit" better than anyone, and in one of her first photographs taken with then-Prince Charles, the young Diana was seen in a colorful sweater adorned with knitted details. She was later seen in a maroon cardigan with reindeer-looking images delicately gracing the collarbone and was pictured in a cozy green sweater in 1980. She knew that the fun knitted sweater trend would one day catch on.

But perhaps Diana's best knitted sweater came in the form of her "black sheep" jumper worn at a polo match in 1980. The bright red pullover featured a pattern of white sheep, with one black furry friend positioned in the middle. It was such an unexpected choice for the young royal, yet it's still just as iconic today. Pop icon Harry Styles channeled Diana when he wore a similar sweater vest while on the town in New York City. So, if campy, brightly colored sweaters sound like your aesthetic, look to Diana for some approved looks.

Statement pants

We all have that one style of trusty denim pants that fits so well we have pairs in every wash under the sun. But if you're a bit tired of constantly wearing jeans, look to Diana Spencer for some approved statement pants. The late Princess of Wales was photographed in 1986 sitting on the front steps of Highgrove House wearing a pair of pink pants! Not only was the color fantastic, but the gingham print stood out against the more traditional setting Diana found herself in. Pairing the statement pants with a pink sweater and a white top peeking out of the collar of her pullover, Diana looked instantly chic but laid back at the same time.

Gingham is a great print to incorporate into your fall wardrobe, and these statement pants have certainly impacted Diana's fashion influence. As noted by Hello! Magazine, the search for replicas has been on as of late, proving that the late royal's 1980s fashion is just as popular today as it was in her day. If pink isn't your color of choice, perhaps opt for a light blue or even a black-on-white gingham look. By mixing up the color palette, you can channel Diana while also making the statement pant your own — simply pair your look with a corresponding pullover sweater, simple jewelry, and a great pair of flat (or take a cue from Diana's gym look and wear some chunky white sneakers) for the perfect fall outfit.

Bold evening wear

We'll be the first to admit that we don't venture outside of our standard nine-to-five often, but when the occasion strikes that evening wear has to be busted out, Diana Spencer's looks should be taken into consideration. Diana's bold evening dress made quite the splash even during her first official outing with then-Prince Charles. Choosing a black taffeta strapless gown, the young Diana looked ever so chic and proved that black isn't just for royal funerals (much to Charles' dismay). People further points out some of Diana's best — and most unexpected — evening dresses, so if you do find yourself with a dressier event on the calendar, take a cue from Diana and opt for a silhouette that is on the creative side.

For instance, Diana's choice of dress for the "Back to the Future" London premiere in 1985 was stunning, as it featured a low, v-shaped back. Diana styled the dress with a string of pearls tied in a knot, but instead of wearing the necklace to drape the front of her dress, the princess swung the pearls to the back so that the dress silhouette was highlighted. Of course, we can't talk about her evening wear without discussing the revenge dress — a black mini number that featured an off-the-shoulder neckline and an asymmetrical hemline. With her corresponding clutch and bold attitude, Diana looked like a million bucks. So, if you are dressing to impress, consider options with interesting detailing and stand-out necklines.

Everyday mismatch

With the COVID-19 pandemic becoming the new normal, many still work from home. Comfy sweatpants and work-from-home attire have ruined our ability to wear jeans for more than an hour at a time, but Diana Spencer may have given us the nod of approval to wear sweats out in public. She was quite the pro at making comfy clothing a streetwear staple, and her take on keeping things casual sparked new trends that stand the test of time.

As detailed by Popsugar, one of Diana's best-mismatched outfits came in 1989. Pictured wearing a matching sweatshirt and sweatpants combo, an oversized blazer, a baseball cap, and her sweats tucked into cowboy boots, Diana looked like any mom of two who through on whatever clothes were available in a pinch — and yet somehow her mismatched outfit looked effortlessly chic, so much so that we're sourcing inspiration from it today. In fact, some of the biggest names in modern fashion have been spotted wearing similar mismatched ensembles. Kendall Jenner, for instance, was pictured sporting an oversized sweatshirt and joggers tucked into a pair of white cowboy boots. So, if Diana Spencer and Kendall Jenner — two fashion icons decades apart — are sporting such a mismatched look, you can too.


Us 1990s kids have a love-hate relationship with overalls. Our moms would force us into them at the young age of five, much to our dismay, and trying to get them off was even more of a chore. But, in the renaissance that is our adulthood, we realize that overalls are a fashion statement, and they're certainly making a comeback. Of course, Diana Spencer would greatly approve of such a look, as she was spotted in overalls even as a royal, proving that the versatile dungaree staple is appropriate for anyone.

As noted by Elle, Diana's all-in-one overall looks came in several ways. She was spotted during a ski holiday in head-to-toe denim, opting for a blue jumpsuit that made her look effortlessly chic. Earlier in her royal career, Diana was seen at a polo match in a pair of pale yellow overalls which featured relaxed legs and a fitted upper half. She paired the dungarees with a delicate floral top and a pair of red wedge heels and effortlessly placed a pair of sunglasses on her head.

"She really adopted this fairytale princess look on the polo field, these very country-core sweet pastels," British fashion writer Eloise Moran told Elle of this particular look. So, if pastels are your thing — or you simply like versatility in your outfits — opt for a pair of Diana-approved overalls.

Bold collars

This is a trend for the fearless among us, but if you want to evoke Diana Spencer's classic 1980s look, you should start incorporating some bold collars into your wardrobe. The late Princess of Wales was often spotted in looks that featured the "prairie collar," Vogue details, and her choice of collar wear was seen on many occasions. In fact, incorporating such visually interesting collars into her wardrobe was seen as a small act of rebellion, stylist Anna Harvey points out, as the neck silhouette disrupted what would've otherwise been safe wardrobe options for the royal. "Fashion might not have been a priority, but she loved to experiment," Harvey told Vogue of Diana's collars, which became synonymous with the unexpected royal star.

Dazzling fashion options with visually interesting collars were seen on Diana at pivotal points in her royal life. Emerging from the hospital with a newborn Prince William in 1982, Diana wore a dress by Catherine Walker, which featured an eye-catching white collar and bow detail. In 1983, she was seen again in what would've otherwise been a darling little mint blue dress, but the intricate collar that reached well past her collarbone made the dress much more interesting. Incorporating this trend is perfect for anyone who loves the cottagecore aesthetic trending on TikTok and for lovers of 1980s silhouettes revamped for the modern era.

Polka dots

This trend is for the fashion-conscious among us who know how to rock a print. When it came to incorporating patterns into her wardrobe, Diana Spencer knew how to experiment. In her early days as a royal, we saw her in grandma-inspired knitwear, gingham, check-patterned dresses, and bold florals. As she got her footing and started to branch out even further, polka dots made their way into the late Princess of Wales' closet. As noted by Vogue, some of Diana's best looks came in the form of polka dots. If you're looking for a Diana-approved trend that'll stand the test of time, this is the one.

Let's take a look at a casual option first. Pictured at a polo match, Diana wore a white skirt with red polka dots, pairing the skirt with a white pullover. What made the outfit that much better, however, was Diana's incorporation of white and red polka dot socks worn with a pair of red kitten heels — the choice was definitely unexpected, and it's one of our favorite outfits of hers to date. Taking a look at a more formal event, Diana was spotted in a white dress with black polka dots at the Royal Ascot in 1988. Her dress became an instant classic and was even replicated by Catherine, Princess of Wales, decades later at the same event. Polka dots might not be for everyone, but Diana proved that the playful pattern could look effortlessly chic no matter the occasion.

Cowboy-inspired boots

We got a glimpse of this Diana-approved trend when we discussed her mismatched outfits. Still, if one element of the aforementioned outfit deserves to stand out, it's Diana's wearing of cowboy boots. Such a choice in footwear was incredibly unexpected, especially for a royal, given the strict fashion rules they are expected to follow (the late Queen Elizabeth II apparently hated wedge heels so much she banned them from being worn). As such, Diana's frequent wearing of cowboy boots, slouchy "pirate" boots, and knee-high boots certainly stood out — if you're thinking of how to dress for colder weather and are looking for a new pair of shoes, why not take a cue from Diana?

Her cowboy boots were seen on many occasions, Vogue notes, including the aforementioned sighting in London and at a polo match in 1988. Diana paired her boots with a great pair of jeans, an oversized sweatshirt, a blazer, and a baseball cap. A few years earlier, in 1986, she wore polka dot trousers tucked into a pair of knee-high black boots, finishing off the look with oversized layers on top for warmth. And, going full cowboy in 1987, Diana was seen at a polo match in jeans (with a bold belt at the waist), a collared shirt tucked in, and iconic boots that gave her a Wild West aesthetic. Such a look takes confidence, but if you're set on replicating Diana's best outfits, don't overlook the cowboy boot.