This winter, after being in lounge wear for most of last year, I’m feeling inspired and energized to play dress up a little bit more. And what better item in my closet to dress up than a leopard skirt?!

A few years ago when leopard skirts came into trend, I put it on my thrift list. Soon enough, I found this one at my local Clothes Mentor (it’s like a more mature Plato’s Closet, in case you’re familiar). This specific one is ‘Express’ and it’s pleated and lined and comfortable enough to wear year-round.

In the Spring and Summer, I wear it with graphic tees, my all-white converse, and a denim jacket. But, I’ve never been super motivated to style it up for Winter, so I thought I would give it a try with some other items I’ve thrifted lately.

First up: what I wore for Christmas

Sweater: Vintage – Purchased in a closet sale on IG
Boots: A Poshmark find (Brand is Wild Diva)

And there’s a fun story about the sweater. About 1.5 years ago, I discovered Erica of ‘Tiny Acorn’ on YouTube. She does all kinds of thrifted and vintage looks, and I was so inspired by a vintage cobalt sweater she had that I put a similar sweater on my thrift list. But, 1.5 years later, I still hadn’t found one I loved. Until… Erica had a closet sale and the blue sweater was up for grabs. So I bought it! This is the exact vintage blue sweater I was so inspired by. I don’t know why, but I love this story, and it makes me love the sweater even more.

Next up: A dressier, edgier (for me) look.

Sweater: Cable and Gauge (Cashmere!) Found at Goodwill
Boots: X Appeal from Off Broadway
Earrings: Upcoming DIY Tutorial

This look would be cute for a Valentine’s date (especially with the earrings).

I have some tall brown leather boots that would look cute under this skirt for a more boho take on it. Haven’t tried it, but I just might. I’ll keep you posted! And…

Before I go, let me just say one more thing (in case you’re actually reading this): wearing boots with a skirt like this is a big deal for me. I’m not tall and I don’t have long legs or thin ankles, so I’ve avoided ankle boots with skirts forever because I thought it wasn’t flattering on my short frame. Now, I’ve said screw it, and I’m wearing what I want to wear regardless of how ‘flattering’ it is. Changing my mindset to focus on how I feel in an outfit, rather than how it makes my body look has been a game changer.

I wouldn’t be surprised if there were lots of you out there who also struggle with the ‘flattering’ versus ‘feeling’ internal debate. So, let me know if you do, or if you’ve overcome it.

And tell me, do you own a leopard skirt? Is it a trend you’re hoping to try? Which of these looks did you like better?