September 3: Ain't No Fashionista

I have a decent sense of humor. I have an incredible sense of taste. If there is the smallest amount of coffee in my brownies, I will discard the dessert faster than you can say, "it's supposed to bring out the chocolate!" I've made do with my other senses, but the one that has gotten the best of me for twenty-seven years is my sense, or lack thereof, of fashion. When it comes to clothes, whether it's buying them, wearing them, or even washing them, I'm clueless.

Up until a few years ago, I only wore shorts. Summer, Autumn, Winter, and Spring. Shorts. Sunshine or rain. It didn't matter. Shorts. I literally had two pairs of jeans (one of which my sister put over a fireplace to dry and burned them rendering them useless unless I was painting or playing in mud) and one pair of black slacks for Christmas and Easter. I never wore my decent pair of jeans because they weren't decent at all. I was under the impression that the "baggier, the better" rule applied with jeans. Oh. And they were cargo jeans.

So imagine my surprise when I ventured into the world of shopping for a pair of jeans and discovered that it wasn't just about buying for 32-inch waist. Loose fit, straight leg, boot cut, low-rise boot cut, regular, and painter. I'm not exaggerating here. Just a few years ago, I had no idea I would have this many options. I ended up getting the straight cut because it sounded better than boot cut. When I finally got around to wearing them out a week later, I was miserable.

I have since decided that boot cut jeans, although relatively uncomfortable at first, look the best on my scrawny legs. I now had a wardrobe of shorts, a few eight-year-old (and up) button-up collared shirts, a whole lot of free t-shirts. I decided it was time for my fashion-savvy sister to take me to the local American Eagle Outfitters (her suggestion) and let her pick out some new clothes.

We were pretty successful. She told me this polo would look good with jeans, this thermal would look good underneath it, that polo would look good with those shorts, and so on. I tried them on and she said yay or nay. And so it went until I had a 100% recycled AEO bag of new clothes. Perfect right? Think again.

In the store, I felt ridiculous in the "vintage fit" polos, but she insisted those were the style and they didn't look bad. Even if I felt comfortable in my new purchases, I didn't know what went with what once my sister was gone. Could I wear the blue, striped polo with plaid shorts? What about the green, striped polo? I bought a blue polo to go with the shorts, but could any of my t-shirts work with them as well?

This is what goes through my head every time I get ready to go out. The American Eagle polos have since been replaced by the old button-ups. As comfortable as the plaid shorts are, they rarely come out of the drawer any more either because I don't know what goes with them. I've had the same pair of tan shoes since my sophomore year of college, but I'm afraid to buy a new pair because I don't know what's cool and hip.

How long can I continue this trend? When is someone going to call me out for wearing the same shirt over and over again? I've tried using my sister's expertise and reading Men's Health for their advice. I've tried finding complete outfits online and even take mental notes of clothes that I think might work but I'm still helpless. I have absolutely no sense of fashion and I'm destined to wear the same clothes I wore in high school for the rest of my life.