How I Somehow Became Even Less Fashionable

So, there's no way to hide that I've never been a fashionable human. When I was in high school, my very favorite shirt was kind of a froggy green and said "NERD" on it in big letters. It had a rip on the side that I kept closed with a safety pin. This shirt did not fit me particularly well, nor did it look particularly good on me. I LOVED it.

Yeah, that's accurate.

We could go even further back and talk about what I wore in middle school, but there could be children reading my blog and I have no desire to pay for the amount of therapy they might need. I mean, really. Middle school was a time of bad decision making for most of us, and I, about as fashion conscious as a barn owl, probably made it worse than necessary. I remember a particular outfit I used to like-- jeans, an ice-blue fleece sweater (not a zip up, a sweater) and all of the ice-blue makeup I could find, including lip-gloss. MMM middle school in the turn of the century.

I have no idea who who this is, but this is approximately how I thought I looked in 1999.
Spoiler Alert: I did not look a darn thing like this.

I've had a lot of favorite clothing over the years. Most of it, like the nerd shirt, has been basically solid-colored and fairly ill-fitting. The result of getting much much fatter than I'd ever anticipated resulted in an amount of body-shame that even my poorly-dressed low-self-esteem middle school self would be terrified of (Which I am slowly recovering... you know what's neat about kindness? It helps to start with yourself!) Self-kindness aside, my clothing for the past two years ago has taken on a particular trend of baggy and dark-colored that nuns would approve of.

Except, the nuns might have me on the fashionable side.

Anyway, as it's clear I cannot possibly be less fashionable, I was quite startled to find that my clothing had taken on a brand new method of not fitting me and generally making me look like a sillypants. That method was being way too big. Today I wore a dress to work and I swear I spent 300% of the day pulling it up. Not a class act when your job is to teach! Meeps! I have pants but hardly any of them fit-- most of them will stay up (by virtue of still having wide wide hips and owning a belt) but they look kind of like I forgot what year it was and decided elephant pants were cool again. My sweaters fall off my shoulders and hang loose on my arms.

Elephant pants, for your reference :)

I know, team, I know this is completely #weightlossproblems #shutup #gobehealthysomewhereelse.

Right now, oddly, it is one of the biggest struggles in my journey. 11 weeks in, I have some pretty firmly placed habits as far as eating and exercising go. I'm down 26.5 pounds and there's no sign of it stopping.

Here's the problem, I should just be a regular ladyfolk and open up my closet and put on my "skinny" pants. However, at some point in gaining weight, I gave up on myself and donated most of my clothes built for a "thinner" Lizzy (AHhahaha, did you like that music joke?) Now I'm regretting that move as I'm nearing the weight I was in January of 2010, when I needed to reinvest in dress clothing. I have bought myself some new stuff, but if I keep losing at the rate I'm at, nothing is going to stay on me for long.

So it is with a strange mix of pride and apprehension that I shop, do I buy this pair of pants in a size down? I can just just squeeze into them now, is it worth it to get them for later?

Team, I've always been a terrible shopper and a terrible dresser. What do I do? Accept that I'm going to look kind of silly for the next year or so? Is there something that can be done? I can definitely hit up some second-hand and thrift stores to help out, but it turns out most of them don't have a nice stock of plus-size stuff, which is what I definitely still am.

Suggestions? Comments? Do you like elephant pants? Should I just stop whining already?