While I would never claim to not care about my clothes or shoes or accessories, I will admit that I like to keep it simple and have been known to wear the same outfit every Saturday night for months at a time. I am constrained by closet space and a choice to spend the disposable income I do have on things like food, alcohol and travel, so I keep the shopping to what I think of as a minimum.
I took this simplicity a little too far a few weeks ago when I wore the same dress three times in one week. Since I am being honest, the truth is I wore the same dress three times in four days. The third time I wore the dress, was to my cousin’s wedding which was one of those challenging black-tie
optional Sunday afternoon affairs. The second time I wore the dress, was to my friend’s 40th birthday party at a fancy Upper East Side club that was supposed to be followed by watching basketball in a sports bar (but was actually followed by a hospital visit to see a friend). Another tough one when selecting the right dress.
The first time I wore the dress is probably the most interesting. At some point on the Thursday of that week, my friend Paul emailed me to invite me to join him at a charity event in soho that evening. We never talked about it, but I am assuming Paul invited me to go with him because his wife was busy and I work in soho and I am often free for last minute invitations and my friends are almost as invested as I am in finding me dates. I was dressed more on the side of casual than business that day and, since Paul has the kind of job that requires a suit and tie every day, I thought maybe I needed to run home and change before the event. This was just a feeling because I didn’t know exactly where I was going and I didn’t know the name of the organization. I did know that I wanted to avoid embarrassing Paul at an event for this mysterious organization he was considering joining. It turns out changing into a black cocktail dress was the wrong answer. The appropriate dress was almost anything other than the same thing one would wear to a Sunday wedding or a Friday birthday party/hospital visit. At this event, there was an artist painting flowers on topless women (and I am pretty sure some of the women were just regular guests at the event who decided to go for it) and the cocktail of choice was a tall-boy of Six Point beer. So there I was, out with a married man, drinking tall-boys, staring at semi-nude women and debuting a new dress. Classy.