Nothing could have prepared me for the shock I would face on my first day of college in Philadelphia. I walked into my 9:30am class and I saw them, girls wearing oversized pajama pants rolled up at the waist paired with equally oversized hoodies, their feet in shower sandals, a half-done up pony-bun-knot thing in their hair. Erring on the side of caution, I assumed this was a classic mistake of oversleeping—what a horror to be late to your very first class! As the the weeks went on, I realized this was no mistake. For these girls, wearing ratty pajamas to class wasn’t a last-minute, accidental thing, it was a lifestyle.
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This way of dressing was so foreign from anything else I had ever seen in my life. In Puerto Rico, where I grew up, looking good and being well-dressed are an essential part of our identity. I was always told to wear nice underwear, “in case something bad happens” (because the ambulance would be like wow look at this girl’s ratty underwear, she had it coming!?). My grandmother dressed up to go to the gas station because you never know who you might run into. I grew up on an island where antes muerta que sencilla, or “better dead than simple,” is a common way to describe our relationship to getting dressed up and looking nice. Not even a lifetime of watching Seinfeld and Friends reruns could’ve prepared me for this.
It’s true that I have experimented with more relaxed modes of dressing, but even those experiments carried with them an effort and purpose. I vividly remember in 6th grade, during one of our “Casual Day” Fridays where for fifty cents we could come to school wearing clothes that weren’t our uniform (the money always went to to raise funds for the school).
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I decided to wear an oversized black graphic t-shirt with some sort of environmental message, black tights, white socks, and hiking boots. It was 1994 and I wanted to be a Grunge baby, except as soon as I got to school, and looked around at all my classmates wearing, you know, regular clothes like pants, I realized I looked like I was in my pajamas (the real purpose of all oversized t-shirts when you are that young). I spent the whole day miserable and embarrassed, and obviously scarred for life, as even now, 24 years later, I can vividly recall the way I felt that day. I would never dress like that again.
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Now, that’s not to say that I was Miss High Maintenance because I wasn’t. I was definitely more of a pre-makeover Tai Frasier than I was a Cher Horowitz. Perhaps as an unconscious response to the cultural pressure to look and act more ladylike, as soon as I hit my teen years and laid eyes on one Gwen Stefani, it was over for me.
I lived in spaghetti strap tank-tops that showed off the colorful bras my mom purchased for me in the JC Penneys’ young girl’s section. I traded the dainty sandals and heels so beloved by my peers and my family for sneakers and chunky boots. Looking back though, it made sense to be attracted to someone like her. Sure, she was a tomboy, but she also always wore red lipstick, she always had her hair done, and the fact that she took the time to bedazzle her bra straps showed effort.
It was a purely superficial rebellion.
I scoffed at the girls who spent hours blowdrying their hair, but in the end we both spent the same amount of time getting ready to go out. We both always made sure that we had something to estrenar, something to debut, when we went out on the weekend; a new top or new shoes, a new way to do our makeup. And when it came time for prom, well, we were all emperifollás or done up like we were about to head off to a red carpet somewhere. Sure, my hair was blue, but it was freshly dyed, cut, and blown out, and I was in a sequined slip dress, and metallic gold heels. I could never stray too far from my roots.
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As I got older, I felt the pull of my roots in more subtle ways, like how I always made sure I would estrenar an outfit on the first day of a job and birthdays, or how I always needed to ring in the new year somewhere fancy so that I would not look overdressed. (It’s important to welcome the new year looking your best so that same energy carries throughout the next 12 months.) I was reticent to fully give into it in my every-day life, but when I would go visit my family during the holidays, I’d let myself indulge, wearing a dress and heels to all events, no matter if they were low key affairs in our own backyard. A few years ago I remember looking around at all the women in my extended family, drinking their Medalla beers in casual jean shorts and halter tops and tall espadrille wedges, looking over at my grandmother in her short fiery red hair, a gold mesh top that showed a beautiful bra underneath, her nails done in a matching gold nail polish, and thinking how obvious it was that all these women had made me.
Recently, in the peak of the heatwave, I put on a pair of jean shorts, a striped linen shirt slightly unbuttoned to show off a yellow lace bra underneath, and a pair of blue Prada kitten heel sandals, I thought about how I was finally joining their ranks as I stepped out into the hot New York City sun. Sure, I had to put on some bandaids on my feet after only two hours, but I looked good. Antes muerta, que sencilla.
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