Okay, so I was scrolling through my Insta feed the other day, and I kept seeing these throwback pics of Winona Ryder. I mean, she’s always been a style icon, but it got me thinking, could I pull off her look? I decided to give it a shot, and let me tell you, it was a journey.

First things first, I had to do some research. I spent hours, seriously, hours, looking at old photos of her. From her early days with the maxi dresses and oversized blazers to her more recent stuff with cool, unexpected details. I noticed a few key things.
- She loved a good band tee. There were tons of pictures of her in loose-fitting tees, especially Tom Waits ones, it looks like.
- Jeans and flats were her go-to for casual wear. I saw a lot of her in worn-in, comfortable flats, blue jeans, and even baseball caps in some pics.
- She could rock a red carpet too. She has worn Chanel on red carpets many times.
- She mixed grunge and girly elements. Her style seemed to effortlessly blend these two vibes.
Armed with this knowledge, I started digging through my closet. I found a vintage Tom Waits tee I’d completely forgotten about. Score! I paired it with some straight-leg jeans and my trusty Converse sneakers. I even dug out an old baseball cap. Looking in the mirror, I felt like I was on the right track.
Experimenting with Different Looks
But I didn’t stop there. I wanted to try out some of her dressier looks too. I found a black, long-sleeved dress and threw a vintage blazer over it. Added some ankle boots, and boom! It was like I stepped out of the 90s. I even tried to mimic her signature short hair with some styling gel, but let’s just say that didn’t quite work out as planned. It was fun, though.
After a week of experimenting with different outfits, I felt like I had a pretty good grasp of the “Winona Ryder style.” It’s all about mixing comfort with a touch of edge, and not being afraid to throw in some unexpected pieces. I might not look exactly like her, but I definitely feel more confident and stylish. And who knows, maybe I’ll even try out a pixie cut someday. Maybe.
This whole experience taught me that fashion is all about having fun and expressing yourself. It’s not about copying someone exactly, but about taking inspiration and making it your own. And it was also fun to rewatch some of my favorite Winona Ryder movies. “Stranger Things” is still one of my favorites.

So, if you’re looking to switch up your style, why not give Winona Ryder’s look a try? You might be surprised at how much you like it.