Who cares about who is best-dressed? If you’ve got money and taste, chances are you dress well. But some of us don’t have money, and we don’t all have taste, and even if we have one or the other, sometimes we don’t use our judgment. We’ve all worn something that we shouldn’t have. Here is an ongoing column about our greatest faux-pas. Feel free to contribute your own stories.

Two years ago, “shirt-dresses” really threw me for a loop. Is it a dress, is it a shirt? Do I have to wear leggings with it on a ninety degree day? On a hot day in Chelsea I chose to rock one, by itself, with a thong. It was fuscia with a key-hole neck-line and safari print. The bottom of the shirt ruffled like a skirt and when I tried the shirt on in the store, the sales-person assured me that the shirt-dress wasn’t too revealing on its own. I used to work in retail, so I should have known better.

So there I was in Chelsea, and it was windy. My shirt dress kept blowing upwards, and I had to press down on it at all times like a child who needs to pee badly. I was late to my job at a night-club. As I walked through the door, my manager, Juan lifted an eyebrow like a total queen and said “Girl what are you wearing?” “A dress!” I answered, as I walked quickly into the coat-check to drop off my purse. “If that’s a dress, these flip-flops I’m wearing are Prada!” he said, flashing me a pair of bedraggled canvas sandals with a tag that brightly announced RAIN-BO. “Whatever, it’s cute. You got a problem with it?” He smiled at me and said “No, but I guarantee you will have a problem with it in a few more minutes.”

As I collecting menus and checked the reservations for the day, every bus boy, waiter, bar-back, and bartender did a double-take and intentionally dropped something to sneak a peak. After this happened four times, I made my way to the host podium, hoping I was safe. The podium was right next to four sets of opened doors, and again my shirt kept blowing up like Marilyn Monroe in real-time. I shut two of the doors and kneeled down to put the door stoppers into the floor. Once I had shut the doors, and looked behind me, there was Juan, with his arms folded, thinking about something. He asked “Are you wearing any underwear?” I didn’t even answer him. I just ran back to the coat check and shimmied my way into a pair of leggings that I had brought with me just in case my fashion chutzpa failed me.

Since then, if I’m not sure if something is a shirt or a skirt I stick to one rule: I don’t wear it.