Why Shapeless Clothing Makes Me Feel The Most Confident

The year was 2012. The dress was kelly green, with thicker, better quality fabric than much of what you'd find at the notoriously inexpensive mall chain where I bought it. The back featured thick black strips of elastic stretched across a cut-out panel. I'm nothing if not a sucker for back cut-outs that still manage to accommodate a bra. I paid the $12.99 or whatever to take it home, thinking that I'd finally found it — the body con dress to change my life.

That $12.99 (or whatever) was an investment at the time. It was the summer before my senior year of college and I had a full-time job in the admissions office on campus, a brand-new pixie cut that essentially made me look like a poodle, tentative hopes that my relationship with food was improving, and a crush on a boy who hadn't texted me all July, but it was fine, I was fine, I wasn't even thinking about him. And now, I had the dress.

Even though I'd been promised that college was where sad girls with mental health issues flourished into cool, edgy, artistic geniuses, it hadn't been working out that way. My anxiety and sadness, which used to act as subsets to my overall personality, had dwarfed all my other qualities and teamed up to prevent me from leaving my bed unless it was strictly necessary.

I was on a journey of self-actualization that summer, and I had pinned all my hopes and dreams about maturing into a confident woman with zero body image issues on finding The Body Con For Me.

All my life I'd been hearing from magazines, well-meaning acquaintances, and television shows that explain how your entire wardrobe is wrong and then give you money to fix it, that as a short, busty woman, I should only wear fitted clothing, ostensibly because my fellow humans weren't intelligent enough to realize I had a waist if they couldn't clearly see it. I spent much of my youth wearing tight sweaters and those horrible, wide belts with square buckles so as not to confuse strangers into thinking I was just a floating head tethered to a pair of legs by a T-shirt dress.

But I kind of wished I was a floating head, or maybe even straight-up invisible, when I wore anything skintight. I would spend the entire day squirming around, trying to contort my body into a comfortable position, worrying about how I looked from every angle. I'd been taught, as girls and women often are, that the only way to be perceived as "sexy" (read: appealing to straight men) is to wear form-fitting clothing.

This idea seemed to be corroborated by the cool, confident-seeming girls I went to school with, who wore stretchy black dresses everywhere — to class with button-down shirts tossed over them, to dances with heels and sparkly purses that were vintage or at least looked vintage. By contrast, my glasses fogged up any time I entered a room and my "going out" wardrobe looked like an 80-year-old Floridian woman and a 13-year-old from Long Island blended their closets together and gifted me the contents (picture lots of sequins and shirts that were loose in the middle and tight on the bottom).

I bought that tight, short green dress in hopes that I would finally become like them. Of course, in reality, there's no "like them." I didn't know these girls well enough to make assumptions about them based on how confident they did or did not seem from 20 feet away. Yet, the entire mission backfired on me. The first time I wore the green dress, I spent the entire night wishing that I was someone else. I didn't feel "sexy" or confident at all. I felt like an alien in my own skin.

I can't pinpoint an exact moment when I decided to say "screw it" to the rules I'd been taught about what I was supposed to wear. Maybe it was when I finally KonMari'd that body con dress in a recent closet clean-out after not wearing it for four years. Or maybe it wasn't one moment at all, but a series of smaller, more subtle reminders over many trips to the mall. Every time I bought something boxy or oversized, I became bolder and more assertive in my fashion choices. The part of me that allowed my dress to dictate how I felt about myself began to wither and die.

I like my clothes to fit me well, of course, but I am drawn to a looser silhouette. Oversized jackets, tent dresses, boyfriend jeans, baggy T-shirts, boxy crop tops — I love 'em all. That's not to say that I never wear items that are more fitted, but I feel happiest in voluminous pieces that allow me to play with proportions.

My green body con from college sat in my closet unworn for far too long, like a ghost of my former self. It made me feel bad because it stood as a reminder of all the things I wasn't and would never be. Removing it from my collection was a symbolic gesture that allowed me to let go of the version of myself that was always trying to please other people, follow the rules, and dress "for my shape."