Unpacking My Love-Hate Relationship With Dresses

Summer dress season is upon us.

One of my earliest outfit memories is what I wore to my first day of pre-school. Sitting in the back of my mom’s cyan-colored minivan (which we affectionately called “blue lightning” because it was kind of beat up but got us from point A to point B), I cried because I was uncomfortable. I hated, I mean hated, tights as a kid. I wanted to wear pants so badly, but my mother had probably made a pretty dress and wanted me to wear it for whatever picture was to be taken. I was miserable. And each time a pair of tights was pulled from my drawer a little tear would run down my face because I knew I was in for a day of discomfort.

In the years following, my disdain for tights was met with a dress code that required skirts and jumpers for most of my adolescence. I went to Catholic school where even in cold weather, I’d often opt for knee socks over tights to go under my cleverly rolled skirts. Tights were too clingy to sit in all day and I liked to wear my soccer shorts under my uniform. On the weekends, I almost never wore dresses, always jeans or jean shorts and a top.

When I moved to New York City for college, though, something shifted. Suddenly, it was almost as though I had never heard the word “pants” in my life, and from now on, anything that even remotely covered my butt was acceptable as a dress. Once my older sister visited me at school, and to her horror, I was wearing a men’s purple graphic t-shirt and nothing else … to work. “They let you do that?????” she questioned, assuming the answer was no and I was about to get fired. I quit soon after and moved on to American Apparel, where this type of outfit was encouraged.

This pants-free habit went on for about three more years, in which I would put on my dreaded tights – filled with runs and holes – just to make a sweater look like a dress. I would sometimes buy a tall men’s tank top at Walmart or Goodwill and wear it with a belt. I don’t even know if I owned pants during this time period. I think I was rebelling in the sense that I kind of looked like a mess with these DIY dresses. It was fun and reflective of where I was at that moment.

When I graduated college – after some breaks and months of trying to get my life together – I lost that sense of apathy toward what others thought of my pantsless ensembles and refilled my drawers with jeans and work pants to look more put together. I remember a friend telling me in the days after I was hired for my first internship, “you know you have to wear pants, right?” And so my complex relationship with what I put on my legs went back to being framed by a dress code that prohibited anything above the knee. Slacks it was, and I hated it too.

Then after I started working in magazines, I went back to dresses, this time, fully trying to copy all the editors I looked up to. They all would wear expertly tailored maxi dresses with white boots. They would float around the office, and even though they were my colleagues, I felt so many of them were untouchable. So, I acquired those dresses to unsuccessfully try to fit right in. Every time I wore them, I looked at myself in the mirror and it seemed like an imposter stared back. I felt more out of place than before.

So when the pandemic came, my wardrobe went back to comfort, which was pants everyday. No nap dresses, just so many jeans.

I think the reason for my endless swing between loving and hating dresses has to do with conformity within different versions of my life. In my college years, ugly, too-short dresses were an act of rebellion. I could wear something that wasn’t meant to show off my legs and do it as I wanted to. I could make a dress look like shit, but also kind of cool. But when someone told me to wear a dress or a skirt to fit into to some arbitrary idea of what a girl’s uniform should be or, in adulthood, how a high-powered femme editor should dress, it was like wearing someone else’s armor. It just doesn’t fit.

I’ve been thinking about this a lot as the summer approaches, and I take a mental inventory of the dresses I own – including those flowy editor dresses that probably have permanent hanger marks at this point. Mostly, I just want to find a balance between that rebellious spirit dresser and the one that just wants to be herself. Can a dress do that? Maybe.

I tried one on to test it out:

If you liked this little essay, here are some more:

The Subtle Joy In Not Finding The Right Outfit

Perfect Clothing Doesn't Exist

A Quick Note on My 15-Year-Old Forever21 Top

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Thank you for reading!!

This Stuff is a newsletter by me! fashion journalist, Alyssa Hardy. Three times a week, I unpack the ways our clothes impact the world through news, essays, interviews and more. Subscribe for free here and follow me on Instagram, Facebook and Twitter.

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