I’m starting to get bored of wearing sweaters with my arms in the correct sleeves and with the “front” actually facing forward. It just feels, I don’t know…dull.

But before you get the idea that I’m the kind of envelope-pushing, creative-thinking, boundary-breaking mind that casually overturns social norms, I’d like to make one thing clear: If I have you fooled, I am a great poseur. Allow me to explain from the beginning.

My mother, a painter, encouraged my three siblings and me to appreciate art and pursue training at different points in our childhoods. My brother brought home prize-worthy, head-turning pottery. My sisters mastered portraiture and mixed media. And I usually created messes more impressive than the attempts at artwork that gave rise to them.

Nothing about the practice of art inspired me. In fact, it intimidated me. My creative process began and ended with shopping—how delicious is that irony? I could spend hundreds of dollars on glitter, glow-in-the-dark paint, stencils, and iridescent paper. But when I brought it all home and laid it out on a table, I froze.

Colored pencils do not come with usage directions. Canvases do not include suggested compositions. The pen—or pencil, in this case—may indeed be mightier than the sword, but only if you know what to do with it. I certainly did not.

I did, on the other hand, know what to do with clothing. There’s only one thing to do with a sweater, right? Put it over your head, slip your arms through the sleeves, and wear it with pants. For a while, I operated under the impression that fashion came with more guidelines than this mystical thing called “art.” I could plunge right into my closet without hesitation and perform the alchemy of putting together an outfit with considerable confidence, because I believed that articles of clothing came with implicit user’s guides.

As it turns out, even a self-proclaimed Uninspired Individual like me can only wear shirts right-side-front for so long before feeling woefully confined by our society’s norms of dress. Also, one time in eighth grade, I got bored and decided to play a game in my closet.

The Rules: Put together a paparazzi-worthy outfit that’s just a bit too cool for your current lifestyle. Pair items that you have never before worn together.

The Result: a cocktail dress featuring photo-realistic cherry blossom trees, paired with biker boots, topped off with a leopard-print jacket.

Sound insane? It was. And I was hooked. My next move was the logical one: Impose weirder rules, do this on a daily basis, and wear the resulting outfit in broad daylight.

The Newest Recipe: Layer things that have no business coexisting. Use two different prints, at least one inadvisable color clash, and an unnecessary redundancy.

The Most Recent Result: Last Monday’s outfit, which consisted of a plaid shirt, worn over a striped t-shirt, teamed with a corduroy mini-skirt, combat boots, and a camouflage scarf.

Feedback in the form of compliments I received while wearing this outfit leads me to think one of two things. It’s possible that my getup was so bizarre that people couldn’t look away and just blurted out a compliment when I caught them staring. But I’d rather believe that my quirky stripes/plaid combo worked because I decided to commit to the sailor-meets-lumberjack bit.

I want to believe that people react positively to the unexpected.

The best proof of this in human form is Leandra Medine, founder of a wildly successful fashion blog called The Man Repeller. If my word isn’t enough to convince you that Medine and team are a force to be reckoned with, perhaps you’ll be swayed by the slew of endorsements they received when Man Repeller hit it big in 2012. Since then, Medine has appeared on Forbes’s “Top 30 Under 30” list, TIME’s “25 Best Blogs of 2012,” Adweeks’ “Fashion Power 25,” Fast Company’s “100 Most Creative People,” and received a Bloglovin’ award for “Best Overall Blog.”

Medine has the fashion world wrapped around her finger for many reasons, but the most important is that she is wildly experimental and uninhibited when she dresses. She is the woman who challenged herself to wear a button-down shirt three different ways and never once put it on properly. She did, however, brilliantly repurpose it as a skirt.

She is the same woman who taught me just last week that I can wear a sweater tied around my neck as if it were a scarf, if I wish to do so.

I very much wish to do so. Because I’m finding that the more fashion risks I take, the more creative momentum I garner. I certainly wouldn’t be alone if I threw a sweater over a dress and made it look like a skirt. Blair Eadie, the Merchandising Consultant for Tory Burch, features this very trick almost weekly on her personal fashion blog. And why stop there when I could wear my skirt as a shirt?

Initially, my love of clothes was predicated on a misperception: that fashioning an outfit is like curating a museum. I thought that I could leave the “creativity” to fine artists and synthesize their work with ease after they’d done the dirty work. Now, I realize that I was completely wrong. In reality, the best dressers, like the best museum curators, are innovative, out-of-the-box thinkers who don’t take themselves—or any industry dictum—too seriously.

You don’t need to spend millions on a designer bag, injure yourself in a pair of high heels, or wear something that makes you feel self-conscious just for the sake of being on trend. All you need is a little humility and sense of humor.

Imagine how much happier, and more fashionable, the world could be if we all took this to heart.

Lily K. Calcagnini, ’18, a Crimson editorial writer, lives in Dunster House. Her column appears on alternate Fridays.