I'm even worse really bad when it comes to buying shoes. They are my Achilles heel of shopping. Show me a cute shoe and I'm a goner. Uncomfortable? That's okay, I'll break them in eventually. Can barely walk in them? That's okay, I'll get used to them eventually. Too small? That's okay, I can deal. Too big? That's okay, a cobbler can fix that (and yes, I can a shoe repairman a cobbler - I'm old fashioned, sue me).
The thing is I am not okay with being uncomfortable, being able to barely walk, or wearing too small or too big shoes. I don't deal with pain well and more often than not those great shoes I bought get worn once by yours truly and then thrown in the closet to rot until next season when I give them another try. And that other try never goes very well.
And I will tell you why it never goes well. Here's the big truth: I can't wear heels. Yes, I said it. I cannot wear heels. They hurt my arches, they pinch my toes, and I look funny walking in them. I'm more of a flats kind of girl (which is unfortunate because I'm pretty short and could use the height).
Case in point, I once was in so much pain that I went barefoot in a really gross bar in the city. And then was asked to put them back on, which was way embarrassing. May I point out that I was very, very drunk and the shoes were still killing me. And to further prove that I can't walk in them, I once put a hole in WG1's toe with one of pointed heels (she still won't forgive me btw). Two very good reasons as to why I should be forbidden from wearing heels.
I hate high heels, but I could not be more envious of those girls I see walking around in the city in four-inch heels. They glide. They look graceful. They seem glamorous. They are the very opposite of me in my ballet flats from Old Navy (last season, but don't tell anyone). More importantly, stilettos to me scream Working Girl -- someone who is a force to be reckoned with, someone you can't push around. And this is why I cannot resist high heels. I want to a be taken seriously while wearing kick-ass footwear.
But then I put them on and remember that heels are just not my thing. I am a flats girl through and through. But it doesn't stop me from envying them - those graceful Amazons in heels stomping through New York City kicking ass and taking names.
Someday I will force my feet into a pair of gorgeous Prada pumps, walk through the halls of my office, and not feel the urge to take them off before lunch and replace them with Uggs. Someday.
But for now I will stick with flats.