How to Dress Like Princess Diana - 4 Iconic Casual Outfits

1. Pink shirt and white dungarees

The first outfit I've recreated is Diana sitting in the garden - I believe this is at Highgrove. She is wearing a pink and white striped button-down with white overalls and white loafers.

I think that it is such a cute outfit, it's so feminine, very classic, and I was able to recreate it with clothes that I have in my wardrobe. I'm wearing a Ralph Lauren button-down Oxford shirt that has pink and white stripes.

I also have my trusty white overalls. These give a bit of a different vibe to Diana's ones because, as you can see, they've got flares, so they remind me of the 70s. Sometimes when I'm wearing them, I feel like the 5th member of ABBA or something!

The only downside about these overalls with this particular outfit is that they come up quite high at the top, so you don't get to see as much of the Oxford shirt as you see in Diana's outfit. I still think that it works and looks super cute.

Diana is wearing white loafers; I don't have white loafers, so I just went with white sneakers. 

2. Pink shirt with black jeans

For the next outfit that I wanted to recreate, I used the same shirt as in the first, although I don’t think that Diana is wearing the same shirt as in the other picture, as this one is solid pink.

Diana has paired her pink button-down shirt with a pair of black jeans, so I popped on my black skinny jeans. Hers are more of a straight leg, but we’re working with what we’ve got. Then I went with my trusty Tory Burch belt - I like the subtle little gold buckle.

Diana has black loafers on, but I’m wearing black ballet flats instead. I’m kind of obsessed with how this outfit looks. I always love a pink and black combo. You get the chic seriousness of the black, and then the pink brings a nice feminine touch.

I think that this is a very classic and balanced outfit, it’s casual enough, but it’s also workwear appropriate enough. Diana knew what she was doing.

3. Sloane ranger

Here I have gone for full-on "Sloane Ranger" Diana. Diana was wearing hunter green boots. I went a little bit out there with my hunter boots and decided to go for an autumn stone red.

I've done my best to recreate this outfit out of things that I already own, so I'm also wearing my jodhpur pants with the boots.

The top section of this outfit is where I became a bit stuck because Diana's sweater is very specific and very intense, and I don't have anything like that, but what I do have is this jumper here that my mum gave to me. I think that this little knitwear number is totally something that Diana would have worn.

I popped a white turtleneck underneath because Diana had a turtleneck underneath her jumper. Because my sweater was a bit longer than hers, I did ye olde belt trick where you put a belt around your waist and tuck the sweater up underneath.

4. Post-workout attire

Lastly, I had to recreate one of Diana’s iconic workout outfits! In the 90s, when Diana was leaving the gym, there would always be paparazzi following her, which was terrible, but it means that there were lots of snapshots of her in various forms of this outfit.

She essentially had a gym uniform that she would always leave the gym in. She would wear biker shorts, a large oversized sweatshirt, then her white sneakers and her gym socks. Also, she would usually wear sunglasses and have some sort of bag that did not match the outfit.

I’m wearing a massive sweatshirt, and then come cute little peach biker shorts, athletic socks, and my Adidas sneakers. This is a very successful recreation!

How to dress like Princess Diana

Recreating Diana’s casual looks has given me even more of an appreciation for just how much of a style icon she was. Anyone can look royal in a ballgown and tiara, but Diana's casual outfits show that her classic feminine looks from the 80s and 90s are timeless.

Let me know what you think of these outfits in the comments below. What's your favorite Princess Diana fashion moment?