Wearing Vintage Clothes in Modern Times
One of my most popular blog posts is titled “Clothing Labels I LOVE From The 1980s & 1990s,” so of course, it only makes sense to follow up with how I style those clothes into outfits for the modern day.
Combining modern and vintage styles is not a new concept for me, but I love an excuse to play dress-up in my closet and share some fresh outfit inspiration with you.
In this post, I will be showing off a giant roundup of newly styled outfits featuring some of my favorite clothes from the 1980s and 1990s that I thrifted and have worn and loved in my closet for years. If you feel like digging through my archives, you’ll come across other ways I’ve worn these pieces, too.
Let’s dig in!
Restyling a Contempo Casuals Graphic Button-Up
Hands down, one of my most worn vintage pieces is this Contempo Casual button-up that features mixed prints.
For this new iteration, I styled it with thrifted wide-leg pleather pants, a vintage purple cardigan, and my favorite pork pie hat.
Grounding vintage with neutral pieces (i.e., black) is an easy way to approach styling loud pieces that you may be unsure about.

Restyling a Floral Blazer
Long-time blog readers will instantly recognize this floral blazer as my “Pretty in Pink” blazer. I call it that because it feels reminiscent of something Andie wears in the movie Pretty in Pink.
I matched the pretty color palette with a modern (thrifted) checkered maxi dress to give it a funky vibe. I think Andie would approve!

Restyling a Vintage Cat Vest
If you’re new here, hi! I love cats. I once shared this vintage cat vest on my Instagram and was surprised to see it circulating really hard on Pinterest in the last few years. I thought it was fellow cat people appreciating it, but it turns out Freddy Mercury owned one with a similar pattern and people thought I had his. Who knew!? (Clearly not me! And it’s not his!)
I normally wear this vest over a basic black dress, but I took a little styling nod from Gucci and mixed it with a garish green and orange combo. It’s kind of weird, and I love it.

Restyling a Vintage Striped Skort
This red sweater vest was heavily featured in a Valentine’s Day outfit post, but this outfit is actually focused on the skort. Yes, skort! I found it last year at a garage sale and was already smitten with the red and white striped pattern. It’s just an added bonus that it’s a skort!
I paired it with a splashy 1980s short-sleeve button-up and a Y2K sweater vest. This outfit is the ultimate lesson in mixing decades!

Restyling a Sequined Parrot Shirt
One of the newest additions to my closet is this long white top with colorful sequined parrots. I love all things parrots, thanks to Claudia Kishi of the Baby-sitters Club, so thrifting this shirt was a no-brainer. Funny enough, it’s by the brand “Emo.” I’d argue there’s nothing sad about this shirt!
I styled it up with lots of colors to really make it shine. Should I tone it down, or do you like the bright look?

Restyling a Vintage Sweatshirt
I thrifted this 1990 “Fashion University” sweatshirt many years ago, and somewhere along the way, I decided to chop off the banded bottom. I low-key regret that decision because I started wearing it less as I grew away from cropped shirts. (Even the ones done tastefully!)
So when I had the idea for this post, I knew I had to include this shirt because I need to motivate myself to wear it again in fun ways. Pairing it with lots of pink is fun, right?!
Yesterday’s Clothes Are Tomorrows Vintage
Thank you for joining me for this fashion time hop! I hope this inspires you to go thrifting, try out some wacky new vintage pieces, or dig through your clothes to wear an old favorite you forgot about.
If you loved these outfits, please be sure to Pin them to try out later!


Wearing Vintage Clothes in Modern Times
