A week after my Tory Burch Eddie Ballet Flats arrived in the mail, I realized with some mounting panic that I had no idea what to say about them. They were…black. They were kind of like ballet shoes? (I now know these are called “flats.”) They didn’t have that big gold Tory Burch insignia on them, which was nice, because those things are the equivalent of the little hood ornament on a Mercedes, in that they screamed to the world that you had enough money to buy expensive shoes and that your wallet probably wouldn’t mind if it found new ownership in someone’s pocket on a crowded subway car. Ya feel me? So these black leather little ballet flats were nice, but they were…well, boring.

To give a little context, I am not a “shoe person.” I own about two pairs of colorful Adidas sneakers that I bought with my own dollars-money. My other footwear consists of two pairs of heels that were part of an experiment, and a pair of Ugg boots that were given to me at an event and that I wear every day because they are bright purple and I love purple.

I also have a kind of screwed up view on what constitutes “boring” versus “interesting.”

For example, these things are boring:
-Brushing my teeth/buying toothpaste
– water (the most boring thing in the world)
– sunlight (overrated)
– groceries
– sleep
– clean, open spaces (Sorry Gwyneth)

These things are interesting:
– Stuff on the computer (mainly YouTube videos but also the SomethingAwful forums)
– Porn (I guess that goes under computers)
– Trying to figure out at what point jeans become jeggings
– Tuna fish
– Alcohol
– James Franco
– Colors!

So in terms of costume design (which is how I refer to my daily wardrobe choices), I usually go for the least “conservative” thing in any shop, which for some reason always happens to also be the least utilitarian item I can find. For this reason, I didn’t own a coat up until a month ago. I find warm clothing “itchy” so I’m usually freezing. My one scarf was stolen from a barn and smells like cigarettes, but doing laundry goes under my “boring” category as well. If my outfits were an art movement, they’d fit right in with Marcel DuChamp and the rest of the Dadists. So yes, my fashion inspiration is “Misplaced Urinal.”

What to do then with these very nice, very understated black flats? Could I wear them as earrings? (Too heavy.) Could I draw on them like Converse sneakers? (Nope, they were black and the magic marker washed right off in the snow.) Were they warm? No, silly, they were flats: If you wanted to wear them to parties in the winter, you had to bring these shoes in your purse and then change into them from the boots you arrived with. Hey, two pairs of shoes for one night? That is boring .

Then came the night where I was expected to go to a big-name media event (jealous??!) and I realized that I could not wear my Adidas sneakers. I could have tried, but I also had a fear that I’d arrive at the door and, like some restaurant scene out of a movie where the guy isn’t in a nice jacket for his date, the sneering butler (garcon?) would make me take off my sneaks and put on some second-hand Manolos they had lying around that were five sizes too small. Plus, even though I am fashion’s version of Forest Gump (I run a lot and have met the president, Jen- nay ) I knew enough to realize that a little black dress + high tops wasn’t a “statement.” It just hurt people’s eyes.

That night, no one mentioned my shoes. I know the shoes “worked” for precisely the reason that no one thought to comment on them all night. Not one single person did that thing where they look down at what you’re wearing and go, “those are so interesting!” in that over-complimentary tone that really means “my mind has drawn a terrified blank in the gaping chasm of weirdness you call an ‘ensemble.'” And even though I’m perpetually in that Catch-22 where I want to be recognized for being different while simultaneously trying to hide the fact that I forgot to wear pants again (I keep confusing “big t-shirts” with “dresses”), there was something adult-ish in the way I didn’t have to explain my footwear to anyone that night, or accept vaguely confused compliments about how “brave” I was being for wearing flip-flops to a catered dinner.

I figured out that night why every girl needs to have those wardrobe staples: the black dress; the Tory Burch flats; the one nice lipstick, and it wasn’t so she’d blend in with a crowd or be “boring.” These were the classy safety nets to prevent against that one day you turn however-old and realize that dressing like a slutty party clown wasn’t cute anymore. Or at least, wasn’t work appropriate. My version of “boring” was what other people saw as “normal” or even “stylish,” and just because they didn’t make some sort of flashy impression or drew the eye immediately upon entering a room…well hey, I always had my amazing personality to fall back on. My amazing personality and those interesting urinal-cake earrings I just bought on eBay.

If you have a piece of clothing that’s meant a lot to you – and you want to share on TheGloss – drop us a line at Jennifer [at] thegloss.com or Ashley [at] thegloss.com