what am i wearing?

Last month, my college friends and I resumed our annual trip after a Covid hiatus in 2020. Per usual, we spent a lot of time planning our trip to Palm Springs including researching restaurants, hiking options and buzz management plans. As our departure date approached, the group texts started to increase in frequency and inevitably the big question was asked, “What is everyone wearing??!!”

I think it is really funny that we are in our 50’s and we have been asking this question for approximately 40 years – basically since our first middle school co-ed birthday party or Bar Mitzvah. When we ask what everyone is wearing, we are basically saying, “I would like to pack for this trip so that when I get there I am wearing something similar to what most people are wearing. I don’t want to look exactly like everyone else but I prefer not to be an outlier. If everyone is wearing shorts and flip flops, then I will wear something similarly casual. But if we as a group are going to be dressed up, I would like to follow suit.”

I definitely believed that by the time I had kids in college I would have the ability to confidently choose three or four outfits without regard for what others might be wearing. But, apparently, I don’t. Hypocritically, I have strongly suggested to my daughter that whenever possible she should ignore trends and completely go for her own style. Yet, even in the safety of a weekend away with women who have known me since I was 17, I still don’t feel secure enough in my own skin to choose outfits without consulting the group.

Whenever I dress to go to a party or event, I generally feel like I have a good sense of how dressy to be and hope to be neither the dressiest or most casual person in attendance (especially at weddings, graduations and funerals where I absolutely do not want to the only weirdo in jeans.) Shooting for this middle safe zone means that I’m rarely the person that has a stand out, trendsetting ensemble. Yet, I strangely envy anyone who dresses uniquely, shows personal style and a propensity to take risks.

For coed events, I feel like as long as my husband and I are somewhat in sync then I don’t need to concern myself with other people’ choices. Lately, however, my husband has been constantly wearing his “hot girl summer” white Stan Smiths so that is throwing me off a little. (He says that they go with everything but I think they are too summer 2019.) Also, I am also still dressing Covid casual and the global supply chain bottleneck is making shopping really challenging.

This week, I am going out with a group of women for dinner and to see “Golden Girls Live” in San Francisco. I was already thinking that I will probably wear jeans or my pleather joggers but then considered that others might be more dressed up. It is very possible that Sandra is going to show up in a stunning silhouette along with perfect hair and make-up. I know a few others might just pop off and wear something amazingly on point.

Given this reflection, I am considering taking this moment to try to grow up and confidently be my own person. I may even listen to Chase Tucker, my new favorite Peloton instructor, who regularly ends class with these words: “I am in competition with no one except the person I was yesterday. And, I am exactly where I’m supposed to be right now.” The lyrics from “I Drink Wine” by Adele also resonate with me right now: “I am gonna learn to get over myself. Stop trying to be somebody else.” (I am easily and often moved to action by inspirational quotes.) Yes, it’s definitely time to stop listening to the middle school girl in my head who is always eager to text, “What is everyone wearing?”