I love planning outfits. Weeks, even a month ahead of time for events I may or may not have coming up. Once, boyfriend mentioned off-hand that we were invited to some girl’s party in a week.I felt insecure and threatened and wanted to look good and cool and pretty. So I bought a new black, patent croc print mini skirt with tulip hems on the sides from ASOS and paid an extra $7.99 for 2-day shipping. We didn’t even end up going to that party and that skirt is sitting in my To Consign pile, NWT (new with tags) because I impulse purchased something that wasn’t quite right out of panic and insecurity.

I eventually found and carefully considered the purchase of the perfect black faux leather wrap mini skirt add to my wardrobe. There was no specific event I had in mind for it. But I knew it would it could be dressed up with knee high boots and a blazer for nights out and parties, and dressed down with a T-shirt and sneakers for casual day looks.

When I got invited to a friend’s Christmas party with two weeks notice, I decided not to stress and buy something new to wear for it. I mentally took an inventory of what was in my wardrobe for what could work. My general philosophy for occasion dressing is: Appropriate and Unexpected. I knew for a holiday party, most people would go for reds, greens, sparkles and metallics. So I wore a sleek, all-black outfit. I paired my black mini skirt with a black velvet/sheer leopard print bodysuit, black semi-sheer tights and black knee-high boots.

There’s something so satisfying, effortless and chic about re-working things you already have in your wardrobe to make them work in the evening. I got invited to another holiday party a week later and wore the exact same outfit with the addition of an amazing Flamin’ Hot Cheetos pin that my boss gifted me.

Even with this newfound confidence in my wardrobe and my ability to put together Appropriate and Expected outfits for whatever occasion arises, I’m still working on buying new clothes for something out of insecurity. I have something coming up where I know someone might be there that makes me feel a little paranoid and jealous. And so I want to wear the perfect thing that makes me look good and cool and pretty.

I had bought a secondhand BCBGMAXAZRIA pink snakeskin print faux leather mini skirt of my dreams off Depop thinking I could get it altered smaller to fit me. The tailor told me that the fabric would be too hard to work with, which was devastating. I’d already been planning outfits around it (e.g. a black mockneck and brown suede knee-high boots) and dreaming of all the shows and nights out I could wear it to. But most importantly, I was going to wear it to this thing where this girl was going to be there where I need to look good and cool and pretty.

And now I realize that the times I do want to impulse buy a new outfit, it’s been out of insecurity and jealousy toward another girl I think might look better, cooler and prettier than me. And that sucks, but it’s good to know so I can move forward with that knowledge. I don’t think knowing that will cure this impulse, but it’ll definitely give me pause the next time I plan an outfit.