Princess Diana’s Style Will Always Be Iconic, So I Built Outfit “Recipes” Based Off 6 Of Her Most Loved Looks, And Now They’re Helping Me Get Dressed Every Day
Hello! My name is Alana, and I used to work in the fashion industry. I'm starting a series where I try dressing like different styles, trends, celebs, or places each month. Last month I tried dressing like a Pinterest Girl, a popular trend on TikTok, and this month, I'm retreating to more familiar territory: Princess Diana.
I'm wearing my late Grandma's coat here. Born in England, she booked a one-way ticket at 19 to the US in 1954, met my grandpa, only to return to England a handful of times. She LOVED Princess Diana, so even though she's no longer with us, this one's for her.
Princess Diana is the people's princess for a reason — not only did my grandma love her, but parents and today's youth love her, too (as evidenced by the many TikToks trying to emulate her style). Her legacy lives on in her charitable endeavors, as well as her impeccable taste.
I can only wish to embody even a hair of her charm and taste, but I wanted to try! The thing about Diana's style is it's so effortlessly and undeniably chic, but also quite approachable. Like, she's a radiant beam of light here, but her outfit is so casual, relaxed, and easy. In a sea of micro trends, seeing this is a breath of fresh air.
So, let's get into all the looks recreated! First, I grabbed the style inspo shot of Diana, then I made a little "recipe" cheat sheet for the look, and then I tried it myself. I only used what I had in my closet, so most of these are interpretations, rather than exact copies. But that's what makes it fun!
1.Alright — here we go! To recreate: Diana's casual chic look
The recipe: blazer + crewneck + jeans + boots + cap
What I love about this outfit is it's so unique, but you probably have most of this in your closet! Grab a pair of straight-leg jeans (the more vintage, the better!), an old crewneck (maybe you can dust one off from college), an oversized blazer (seriously, I bought one last year for $4 at Goodwill), a hat, and boots. Obviously, Diana's and the recreated outfits use cowboy boots, but I also think this could work with any other calf-length boots.
Clothing links: Blazer; Crewneck; Levi's; Boots; Vintage Detroit Hat; Earrings
The result in real life:
I made two ideas using the same bottoms but a different crewneck and blazer combo to show that this is a *reaaally* simple combination. And if you're like me and overdid it with the oversized blazer trend, you're in luck. Put 'em to use!
Special shoutout to the jeans — they were my mom's in the '80s! And on the right, I'm basically an ad for Target x Rowing Blazers (both the top and blazer are from the collab). Rowing Blazers just recreated Diana's iconic sheep sweater... It's an A+ brand when it comes to emulating the preppy side of Diana's style. I dream of affording the real brand, so I practically ran to Target when I saw they were doing a Target collection in the fall!
The side-by-side:
2.Onwards! The look to recreate: Diana's varsity jacket/school drop-off outfit
The recipe: varsity jacket + skirt + long sleeve + chunky belt + hoops + tights + loafers or flats
Alright, first off, can you believe she looked THAT good dropping her kids off at school!?!? The base of this outfit is quite simple: plain black shirt, skirt, and some tights. Annnd for those that are sticklers on not wearing color, it's essentially all black, so you're in luck.
I liked the idea of updating the look a little with a pleated skirt and loafers, but it's solid either way. You could wear the base of this outfit perfectly fine on its own, but I love that addition of the varsity jacket to make it more casual. Sooooo if you've been wondering what to do with your dusty old high school varsity jacket, this is your chance!
Clothing links: Varsity jacket; Long sleeve; Belt; Skirt; Tights; Earrings
The result in real life:
I personally am not sporty nor do I play any cool instruments, so I borrowed my partner's drumline jacket from college to create the look. I did, however, have an old '90s skirt and some sheer tights so that was easy peasy. Personally, I can't imagine dropping kids off at school in this, but I sure as hell would feel pretty chic!
The side-by-side:
3.Next! The look to recreate: Diana's Canadian ski tuxedo
The recipe: a Canadian tuxedo! (Jean shirt + jeans) + leather bomber + ski boots/boots + belt
Okay, so, this look might be the most controversial — you either love or hate all denim looks. But as I have said before, denim on denim is never really going away. And I think Diana is just proof that it can look fab! This whole denim ensemble is from Levi's. The accessories are give or take depending on what you have — I swapped ski boots for cowboy boots to keep the more western vibe (and for more everyday practicality).
Clothing links: Bomber; Western shirt; Jeans; Belt; Boots; Earrings
The result in real life:
I was not sure how I felt about this one, but I actually didn't hate it??? I think of all the outfits, this is the closest to Diana's original fit. I did like it better without the leather jacket, though. I sadly don't have one oversized enough (unless I scuffle through my dad's closet).
It's pretty ~country western~ and definitely not for everyone. However, I didn't think I'd ever wear this one, but I actually loved how it made me feel once I had it on! So if anyone wants to invite me to a country music concert...or maybe I'll wear this skiing this year to truly embody Lady Di (though I can't imagine I'd have great movement in jeans).
The side-by-side:
4.The look to recreate: Diana's effortlessly chic outfit
The recipe: white button-down + jeans + belt + loafers + optional matching accessories
The simplicity of this one is *chef's kiss* 👩🍳😘. I'd be shocked if you didn't have most of this already in your closet. It's such an easy outfit, but I think it looks universally good on everyone (I saw so many people recreate this one on TikTok!).
The result in real life:
What I love about this outfit is it seems so obvious, but I've never really gravitated toward putting this together. So I always consider it a huge win when I have a new everyday outfit to add my wardrobe! ➕1️⃣
For the look, I didn't have the right colored tan belt, but I think it works fine with any neutral brown, tan, or black belt. I also don't think you have to wear loafers to achieve this look — I'd probably choose a clean sneaker over what I have on (or if I had loafers that matched the belt).
The side-by-side:
5.The look to recreate: Diana's iconic workout outfits
The recipe: Crewneck + bike shorts + dad sneaks + sunnies + tote/gym bag (optional)
Arguably the most famous of Princess Diana's looks, the crewneck + bike short combo completely took👏over👏 the👏streets👏 this fall. And even though we are entering a new season, I don't think this will go away! It's so versatile for everyday wear — sure, you can wear it to the gym, but I'd also throw this on to run errands, walk the dog, and maybe this one would be more practical to pick up the kiddos from school.
Clothing links: Crewneck; Bike shorts; Sunglasses; Sneakers; Bag; Slouch socks
The result in real life:
Here's my try at it! Wearing the Rowing Blazers sweater again (I can't get enough...also, in case you couldn't already tell, Michigan is my alma mater so I naturally gravitate toward maize and blue). I love this one!!! There's only one issue with it... Is it possible to wear an outfit *too* much?
Personally, I say no! Rewearing outfits is sustainable and resourceful. What's also great is I can just keep swapping out the crewneck for a completely new outfit each time. Yes, I will be wearing this Diana recipe until it goes out of style. (But it won't!!! 😉)
The side-by-side:
6.And finally, the look to recreate: Diana's "quiet luxury" polo outfit
The recipe: sweater + layered button-down + trousers + optional matching shoes/accessories
Ok, I finally understand the "quiet luxury" style everyone was obsessing over this year. Sorry, Sofia Richie (love ya), but Princess Di *is* the blueprint. Yes, Diana wore this to a polo match, and no, I definitely don't have any polo matches to attend, but I WILL play pretend by trying to recreate this look!
The result in real life:
Ok so...here's my look, and I actually think it's a slay!?? 🤭🗡️ No, my crewneck is not backwards, and no, I didn't try to recreate this three different times — it's giving effortlessly chic, ok!!!
But in all seriousness, this is probably my favorite look because I followed the guidelines (sweater layered with a button-down + trousers), but I diverted a little in the styling. I didn't have any white straight leg pants that fit (I actually tried putting some on from high school, but they were waaaay too tight), so I decided to just wear these gray ones I had with my little pointed booties (love how they peep out of the pant leg!). Clementine the cat said it's a slay...and I kinda have to agree!
The side-by-side:
Alright, that's a wrap! While I was a tad scared to try and emulate a style icon for the public, this was actually so much fun. And after trying out some of Diana's iconic looks, I truly think it's possible for anyone to put their styling magic to the test and try out these Princess Diana outfit "recipes"! This could be you:
Let me know if you try any of these out, and if there's anything I should try next! XOXO, see ya next month!
