Okay, so I’ve been totally obsessed with Winona Ryder’s style lately, especially her 90s looks. I decided to try and recreate some of her iconic outfits, and let me tell you, it was a journey!

Getting Started
First, I scoured the internet for pictures. I mean, I spent hours on Pinterest and Google Images, just saving every photo of her I could find. I wanted to get a really good sense of her overall vibe, not just specific outfits.
What I noticed was a lot of black, obviously. Lots of leather jackets, band tees, simple jeans, and boots. It’s all very grunge, but also kind of effortless and cool. She doesn’t look like she’s trying too hard, you know?
The Thrift Store Haul
Next, I hit the thrift stores. This was crucial, because I wanted that authentic, worn-in look. Plus, it’s way more affordable than buying everything new. I was on the hunt for:
- A black leather jacket (obviously).
- Some vintage band tees – I was hoping for The Ramones or something similar.
- Plain black or dark wash jeans. Straight leg, nothing too skinny.
- Black boots – either combat boots or something a bit more sleek.
- A simple black dress – something I could dress up or down.
I got lucky! I found an amazing, slightly oversized leather jacket that looked like it had seen some things. I also scored a couple of cool band tees (not The Ramones, sadly, but still good) and some perfect, worn-in jeans.
Putting It All Together
This is where the fun really began. I started experimenting with different combinations. One day I’d wear the leather jacket, a band tee, jeans, and boots. Another day I’d try the black dress with the boots and maybe a denim jacket tied around my waist.

I also played around with accessories. Winona often wore simple silver jewelry, so I added a few thin necklaces and rings. Sometimes I’d throw on a beanie or a baseball cap, just to change things up.
The Final Verdict
Honestly, I loved it! It felt so cool and comfortable, and it was definitely a departure from my usual style. It wasn’t always perfect – some outfits felt a little too costume-y – but overall, I felt like I captured the essence of Winona’s 90s style. And it was surprisingly easy to do, thanks to the magic of thrift stores and a little bit of inspiration.
It’s a style that I added a bit to my daily look.