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Shopping For the Fashionably Challenged

I hate shopping. In fact, I'm borderline Fashion Challenged, having gathered up all my hoodie sweatshirts and 10-year-old yoga pants eons ago so we could hide together under a rock, far from the trendy magazine knowledge and image awareness so often required at the mall these days.
So, naturally I was intimidated when I won a gift certificate to a cute, online boutique. The shop was full of sweet dresses, vintage skirts, and flowy blouses. Nary a pair of yoga pants to be found, and no housewares or kids' departments to divert my attention (or funds). I had no choice — I had to spend the money on new clothes for myself. It was a rare opportunity to turn over a new leaf, and maybe even turn up with a new wardrobe.
I agonized over the selection. Countless adorable garments begged to become the new me, but was I ready to change my whole style? Would I really start wearing dresses if I owned some? Could I be a hat person? Some outfits seemed perfect, except I couldn't tell how well they'd translate to anyplace other than the preppy sailboat where the model was lounging — not to mention how well they'd translate from the model's size zero body to my somewhat-quite-larger-than-size-zero body.
Gradually gaining confidence, I clicked several possibilities into my cart and then perused my haul. It was at this point I checked the prices.

Rookie mistake. Shoulda done that first.
Loosely moored back in reality, I began deleting my new identity, piece by piece. The gift card wasn't going to buy me a whole new wardrobe, it was going to get me either one gorgeous dress that I loved but would probably never wear, or three plain t-shirts, on sale, identical in every way except color.
As you can probably guess, I got the shirts.
However, determined to force myself out of my comfort zone, I hit another online site to snag a few things on the cheap. I decided to give jersey knit maxi dresses a shot. After all, they're practically full-body yoga pants, right? I could look like I'd changed out of my pajamas, and still be comfortable. Winning!
The t-shirts arrived, as did my new "I'm Casual But I Do Care A Tiny Bit About My Appearance" dresses. Here's what I learned:
  1. Designer t-shirts automatically get put in the "Too Nice To Wear" category. They're always passed over in favor of crappy old t-shirts that are immune to being ruined because I've already spilled coffee on them 100 times.
  2. My capris were camouflaging more hip lumps than I gave them credit for.
  3. I have an irrational fear that wearing a skirt outdoors is an invitation for grasshoppers to jump upwards toward my netherparts.
  4. Leg stubble is like Velcro for jersey knit fabric.
  5. I am, indeed, not a dress person, nor do I ever attend any functions worthy of a "good" t-shirt.
  6. I hate shopping.
This article originally appeared on In The Powder Room in July 2013; reprinted here with permission.

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