Dress For Princess Diana Fall Without It Looking Like Cosplay  

Princess Diana’s fashion for fall? Groundbreaking. But TBH, out of all the autumnal trends over the years, like *shiver* infinity scarves, jeggings, or those suede slouchy boots from the early oughts that were meant to go up to your knees but would inevitably fall down to your ankles, making you look like a pirate — which is one of our “favorite” early 2000s trends that’s making a comeback. (Hopefully, the boots stay up this time).

Princess Diana’s style keeps coming back each fall like the foliage (pretty sure we won’t be saying the same thing about Brat Girl Summer…don’t @ me). Similar to how Marilyn Monroe’s red lip or Audrey Hepburn’s little black dress has become iconic, so has Princess Diana’s effortlessly cool layered preppy timeless vibe.

But there is a fine line between dressing like Princess Di and looking like you’re dressing up as her. Especially since this trend happens around spooky season – and nothing is spookier than looking like you’re in a costume when you’re not (as a theater kid, I get it).

What is Princess Diana Fall?

When you think of Princess Diana’s style – you’re likely thinking about her athleisure aesthetic of a baggy varsity sweatshirt, biker shorts, chunky socks, and sneakers. Or maybe you’re thinking of her red sheep sweater with the one black sheep that has become the chicest of ugly sweaters; just ask Bowen Yang.

Princess Di’s style can best be described as a mix of “comfort and a laid-back polished feel” that hits “that perfect sweet spot between cozy and stylish,” said stylist Sharon Warton. This basically describes how you want to dress when it gets colder (any day now): Cozy, with enough style, so you don’t accidentally channel the Michelin Man.

Why does Princess Diana Fall Keep Coming back?

Lilliana Vazquez, style architect, and creator, who has a real talent for showing you how to choose timeless pieces that are worth the investment in her This Not This series, thinks Princess Diana’s style comes back each year because of how tricky it is to dress for a transitional season like fall — something even Vazquez, a professional stylist who always looks flawlessly put together struggles with when dressing herself.

“When you have these very iconic images of somebody who carried themself with so much elegance and just really understood how to dress for their body, you kind of use that as your north star for getting dressed in these tricky more transitional times,” she says. When you search “Princess Diana Fall” on Pinterest or TikTok, not all those pictures were actually taken in autumn, but because London’s weather is all over the place (like fall in the States), these looks make sense to use as inspiration during our Pumpkin Spice Season.

As this style keeps coming back each fall, the more classic and iconic it becomes. “Her style has a kind of effortless elegance that people always want. With athleisure and comfy-chic fashion always on trend, her looks will stay timeless,” said Warton. Vazquez agrees adding, “I really don’t think that we’re ever going to tire of her looks, I think if anything it makes me sad that we don’t have more.”

How do you pull off Princess Diana Fall without it looking like cosplay?

“It’s all about balance…Avoid going overboard with accessories or trying to recreate it exactly. The trick is to take inspiration from her style without copying it head-to-toe,” Warton says, adding that you can keep Princess Di’s style fresh and modern by sticking with a simple color palette and combining her timeless pieces like a great fitting black or navy blazer, fresh white sneakers and neutral sweatshirts with modern staples since, “Diana’s style was all about looking polished but not overdone.”

Masterfully layering is key when it comes to embodying Princess Diana’s style and it can be subtle, “like adding a white t-shirt under a crew neck sweater may seem really insignificant but seeing that pop of white at your neck really adds some depth to the look and some dimension,” Vazquez adds.

Lauren Morales, the manager, buyer, and stylist at Polkadots & Moonbeams, a modern and curated vintage store in Los Angeles, knows the challenge firsthand of keeping vintage pieces looking fresh and not costumey, especially when it comes to the eighties, a decade Diana gracefully dressed her way through.

“The eighties are so hard because that was such a lull in fashion, like the over-the-top, the excess, the crazy diamonds, rhinestones, glitter, and sequins. It’s like everything got thrown in the pot, but she was somehow able to navigate that late eighties and early nineties with chic looks that everyone still copies forever,” Morales says, showing how to make Princess Di’s fashion modern in a recent post that styles a pop of red with neutrals like all black or all white outfits, or by adding some edge to basics like a stripped navy cardigan with gold buttons short set by adding equestrian black leather boots.

Avoid the overly pinned looks

Image Credit: Getty Images

When it comes to using Princess Diana’s style as inspiration, Vazquez suggests following the less Pinterest-ed images that might be under the radar, like Anya Taylor Joy did when she wore head-to-toe red. “The second I saw her in that, I was like, that is one thousand percent Princess Diana inspired. There is a photo of her with red tights — what royal would ever wear colored tights? She was doing this before we ever thought of doing this,” Vazquez said. Princess Di walked so Blair Waldorf could run.

Red Tights

Red Blazer Dress

When you think of Princess Diana, you might not immediately think of animal print, but that’s another under-the-radar style of hers, like this leopard swimsuit she wore on vacation. “She was a huge fan of leopard print, but she did it in such an elegant way, like she didn’t do it mob wifey. It always felt like it was really subtle, elegant, and elevated,” Vazquez says, who suggested channeling this look today by wearing a leopard bodysuit under a black blazer with black trousers or having it as an accessory like a leopard pump with jeans a T-shirt or with all black. “Instead of having it be this very loud moment, almost have it be this accessory moment,” Vazquez explains. “It’s more ‘refined‘, which is a word I think of a lot when I think about her style. She managed to pull off these big, bold prints or these big, bold trends in a really elegant way.”

Image Credit: Tim Graham Photo Library via Getty Images

Leopard Print Bodysuit

Leopard Print Heels

In addition to avoiding overly pinned looks of Princess Di, Vazquez also suggests considering if the look you’re trying to recreate “was a huge part of the wardrobing of The Crown that feels very identifiable,” which can also make this style “feel costumey.” Such as Di’s off-the-shoulder black velvet mini “revenge” dress with a chunky jeweled choker or the iconic sweatshirt with bike shorts. Vazquez recommends making these looks your own. For example, with the bike shorts, “maybe throw a blazer on over it and do it with a flat instead of doing it with the high socks and the sporty sneakers. I always say take these images and let them be a springboard to your style.”

Invest in a timeless blazer and denim

The cornerstone of Princess Di’s style, which will continue to be a wardrobe staple, is a good-quality blazer and denim. “A classic blazer on anyone, no matter what your body type is, will always be in style,” Morales says. “Same with a great pair of Levi jeans. It’s always going to come back in some capacity. If it’s 2024 or 2014, you’re always going to see those same styles. They’re evergreen and interchangeable no matter where you are. They always work.”

When shopping for that perfect blazer, Vazquez recommends looking for one that has “a beautiful shoulder, a cinched waist, is lined and has beautiful button detailing… whether it’s black or chocolate brown or even a houndstooth that you can literally throw on over everything.”

Image Credit: Photo by Tim Graham Photo Library via Getty Images

Oversized Blazer

White Denim Jeans

As for the denim, turns out you can tuck your jeans into your boots again, like the Princess of Whales so masterfully did — without bringing back the jeggings or skinny jeans. Instead, Vazquez suggest looking for denim like the pair she’s wearing in that above video that’s “slim enough, it’s the same exact width at the knee to the ankles so you can get them into a boot, it’s just not going to have that early 2000s skin tight jegging [look].”

So invest in that classic blazer and denim, play with a pop of color or animal print, tuck your boots into your non-skinny jeans, and relish in Princess Diana fall. Just remember if your look is all over Pinterest or The Crown, you’re probably doing too much. Make this Princess Diana Fall your own, and you really can’t go wrong *slowly takes off Princess Diana wig*.