Do It Like Diana: Oversized Sweater Trends Fit for a Princess

The ever influential Princess Diana's style lives on to this day as 90's fashion circles back into the mainstream media. With the oversized sweater trends popping up all over Instagram and popularized by celebs (I'm sure Ariana Grande comes to mind) I thought I would go a bit in-depth into Lady D's fashion history for inspiration. 


Diana was seen leaving a workout wearing the classic 'Athleisure' combo: bike shorts and an oversized sweater. I want to do a post about Diana's Athleisure style fashion and highlight her love for bike shorts. For now, as I stick to sweaters, I'll point out the pattern that you'll see in a lot of Diana paparazzi shots. 

This was her classic fit for any and all workouts. In the left photo: This sweater is from Virgin Atlantic, and copies of the sweater can be found all over the internet for purchase.  Her white shoes are brighter than any sneakers right out of the box and peep the rolled down socks. So incredibly 90's. 

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I thought I was doing something unique pairing a college sweater with some shorts, but Lady Diana had this art mastered years before I was even conceived. Here we see the classic white bike shorts below the sweater, striking fear into the hearts of all women that don't own nude underwear. Celebrities these days have openly stated that they love to copy this look from her. 

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The large sweatshirt with a slightly business-minded looking cream skirt and shoe combo can make any look a bit more relaxed. The USA sweatshirt she's wearing on this rainy day is contrasted by a black tote. I really like that she wasn't afraid to match a bright white sweatshirt with a cream skirt here, and I think it works well on such a dreary day.

Shop Inspiration:

Disclaimer: All photos below are from the ASOS website. By clicking the link, Sincerely, Alice does not profit in any way. These are just some sweaters I found cute and fit the theme of this post. 

For the looks below, the focus was on a fun and vibrant looking sweater that would pair well with bike shorts and gives that kind of 'vintage vibe'. I accidentally ended up with a blue/purple pastel palette, but I really like it! 

When I saw this sweater, I knew I had to add it to this list. I tried to specifically pick things that weren't too expensive (aka things I could buy and not feel too bad about it) and this sweater is the most expensive on this list. The font read as very 90s and the bright whiteness of the sweater was something I think Diana would really go for.

The half zip really stood out to me, as well as the decal of the American flag. I really like the way this piece is styled as well, as the jeans give me a 90s/80s vibe that felt almost androgynous. 

I found a college sweatshirt! Feel free to use your alumni hoodie as a substitute for this one, but if you don't have a comfy college sweater yet, this one may be for you. The text that's slightly curved in the center gave me the same kind of vibes as Lady Diana's Harvard sweatshirt.

Lastly, I loved both the color and neckline of this sweatshirt. The sleeves seem puffed from the shoulders which gives it even more of a retro vibe. While I'm not sure I would catch Diana wearing a pastel purple turtleneck, I think that this look really captures the decade as well as the comfy-cute factor.

I'm no expert in fashion, but I had a lot of fun making this post. I love looking into older fashion trends and analyzing why they are still iconic today, so while this is a different kind of post for me, I hope I can make one again very soon.

As always: thanks for reading!