Lily’s Top 10 “WTF Was I Thinking?” Clothing Purchases

I wouldn’t say I have a shopping “problem.” It’s more like a really dedicated interest in what I consider to be one of the more exhilarating sports on earth. As with any great athlete, though, I sometimes screw it up. And even floating in the ever-expanding sea that is my wardrobe, those screw ups make themselves known, like an endless loop of whiffing on a goal playing every ten minutes on ESPN. Alright, that’s enough with the sports metaphors. Jessica, Susannah, and Leo, I’ve got you beat…

  1. An Agent Provocateur Corset. I don’t regret owning a corset; corsets are totally badass. I do, however, regret spending $370 on one that I knew didn’t fit my chest at all, convincing myself that I would wear it IRL with blazers and pencil skirts for a dirty librarian sort of vibe. The only vibe you get from that thing is porno.
  2. Amphibian-encrusted handbags. Who remembers a couple years ago when Marc Jacobs put frogs on everything? I do. Mostly because I bought not one, but two purses with large silver frog clasps. To this day I can’t follow through on using either one of them.
  3. A modern day Cleopatra mini dress. See the dress at left? I have that. Mine has black lining and is longer — though admittedly by only about two inches — but yes, purchasing what is essentially a gold fishnet dress once struck me as a great idea. A few weeks ago, I wore it for the second time ever as a $1,600 costume. And got dizzy from the shame spiral.
  4. Shoes a full size too small. There were these glorious Christian Louboutin loafer pumps when I was a senior in high school and I decided that I needed them. While I maintain that they were absolutely necessary to my continued existence, my decision to buy them a full size too small because that was the last pair still haunts me. I couldn’t walk in them without experiencing excruciating pain half a block in.
  5. A black wool, floor-length YSL skirt. I am not Amish. Apparently I forgot that for a minute, though. I blame the sample sale blinders that prevented me from noticing anything beyond the fact that the $1,800 skirt was marked down to $250.
  6. Most of my high tops collection. Don’t get me wrong, I love a good pair of kicks, but I probably don’t need 25 pairs, given that my typical wardrobe doesn’t exactly mesh with bright, high-top Nike Dunks.
  7. A silver Burberry trench. In theory, I like the thing. In practice, I look like a confused robot trying to be a real girl.
  8. A beaded chiffon Phillip Lim tutu skirt. Not. Flattering.
  9. Designer man suspenders. File this one, along with the corset, under things that actually only work in porn. Or on a dude whose man boobs won’t make lovely, tailored suspenders somehow look insanely slutty.
  10. All 50 of the too-small or too-big bras I own. Okay, so underwear shopping makes me nervous. I’m too old for that to be okay, but the hot flashes and stammering that accompany buying new bras for me don’t seem to be going away. Those nerves often result in an unwillingness to ask for another size and panicked purchase of bras that don’t actually fit, like, at all. Despite being a pretty solid 32DD, my underwear drawer spans everywhere from a 34C to a 32EE. FML.