How to Dress in Your Twenties, According to Movies

Collage by Zoë Gigis

There are approximately one trillion things that differentiate my life in this apocalyptic hellscape from that in the great before (yes, this is a Pixar reference; no, I’m not a Disney adult). For example, I used to entertain the illusion of a work-life balance and the hope I’d meet my soulmate at a crowded coffee shop or on the subway during rush hour. Another thing I had before it became famously no longer viable: a fashion sense. 

I didn’t love clothes in the same way Instagram bloggers do, with grids so tightly curated that the Smithsonian called to say it's getting bangs and moving to Europe to find itself. For me, clothes were like my mom’s childhood best friend: they reminded me that, honey, you’re young, you’re hot and you should text her son, who just broke up with his shiksa girlfriend.

But that was before clothing became purely utilitarian. Now, I change into my day pajamas so I don’t wear out my night pajamas. The stretchiness of a pair of leggings determines whether my daily activity will be a thrilling trip to the grocery store or rousing walk around the block. I’m like a character in a dystopian YA novel forced to wear a government-issued jumpsuit, but less chic.

This loss only really came to my attention after I revisited films and television shows I’d adored growing up; ones I hadn’t fully understood but had latched onto as a kid. Some of the hits include Girls, The Devil Wears Prada, Chewing Gum and Legally Blonde. 

I was obsessed with any film with a makeover montage or peeks into characters’ closets, probably because I was canonically ugly until *checks mirror* yesterday and they gave me hope  of an anxiety-free adulthood. These were women who went to costume parties and wore heels to work. What more could I possibly want?

Initially, I gravitated toward these films and shows to sink into the familiar and to give me something to do other than eat Chex Mix while staring at a wall. But, splayed on my bed in a high school lacrosse tank, I realized that this content was the reason fashion became so intertwined with my impression of being a person in their twenties. There was a joy and free-spiritedness that came across through each wardrobe and that association informed my idea of what it meant to be twentysomething (oldest child vibes, much?). 

Watching Girls when I was younger, the way the show used fashion went over my head. I didn’t see how Shoshanna’s sugar-coated closet signaled naivete, how her taste for popular trends stemmed from a deep ache for acceptance and camaraderie. I also never would’ve clocked Jessa’s transformation from eccentrically unstable to uniquely tame from her altered appearance, as she goes from wearing a black feather dress to embroidered varsity jacket. All I knew was I couldn’t get enough of the big scarves and costume necklaces. Disclaimer: I only made it through the first season because Adam Driver used to scare me.

Some part of me understood that Andy’s wardrobe revamp in The Devil Wears Prada indicated a transition from wide-eyed ingénue to sophisticated bitch lady, but like in a good way? It was only later I realized it’s really a film (ahem, cinematic masterpiece) about ambition, overachievement and, ultimately, disappointment. 

I tried to reconcile my former impression of a person's twenties with my reality. One difference between my life now and the before times is that my clothes made me feel like I was presenting some version of myself that felt true. Not having that validation is hard and figuring out what to do about it is even harder. In short, please email suggestions for feeling good to my assistant, who is actually just me using my “phone voice.” 

I guess if I’ve learned anything from this “journey” it’s that I used to think being in your twenties was all about open-mouth laughter with friends over margaritas while wearing an oversized blazer. A small part of me thought, or at least hoped, I’d be a fully-formed person (read: billionaire CEO sex goddess) by my twenty-fourth birthday (hey, stop laughing!). I didn’t understand that this age still revolves around rejection and re-evaluation, pandemic or not. These films were trying to tell me all along, but I was too busy picturing myself in a neon mesh tank and pink wig to notice.