Monday marks the 6th anniversary of when I first started working post-college. After a summer of European travel followed by aimless afternoons spent reading the entirety of the Harry Potter series on pool floats at my parents’ house and generally overstaying my welcome everywhere I went, I finally bucked up and made my first tentative steps into becoming a productive member of society.

That transition into actual tax-paying adulthood from lovable Mark Ruffalo in You Can Count on Me-esque quarter-life-crisis-courting post-grad is, to paraphrase both Paul McCartney and Sheryl Crow, a long and winding road, every day.

With any entry-level hire, there are some obvious hurdles to get over, like navigating office politics and the art of the perfect work email greeting and closer. There are also some other, trickier tasks, like the trial and error process of discovering the appropriate level of drunkenness at company happy hours and the best way to ensure your breath doesn’t smell like an ashtray dipped in Absolut at your 9am meeting the next day.

I mastered many of these tasks years prior as a problem child at my father’s company social outings like a true old soul—an old soul who excelled at getting secretly drunk at age 16 at a sales retreat in the Dominican Republic—but I did find myself grappling with one unexpected challenge: the dreaded business casual dress code.

Even the name 'business casual' makes no sense to me, as there is nothing casual about my business. My business is fucking fancy.

As a PR assistant at my first place of employment, I was informed that I would need to adhere to a strict collared shirt, khakis, dress shoes regimen every day. Not a full on suit, mind you, as that wouldn’t mesh with the “young creative” vibe the company hoped to portray. Also, curiously, our young creativity did not apparently extend to facial hair, as we were instructed to shave every morning. Stubble is so stifling! And since we already had the casual part on lock, the thought of implementing casual Fridays was only spoken about in hushed voices, the way young revolutionaries discuss the promise of a better tomorrow under democracy, or how Kim Kardashian reveals her secret attraction to Caucasian men.

To begin with, my wardrobe generally has two speeds only: casual bordering on homeless or a formal tuxedo. I don’t know why I go to extremes either, Billy Joel, but I do. That middle ground—simply looking “nice”—has never been my strong spot. Even the name “business casual” makes no sense to me, as there is nothing casual about my business. My business is fucking fancy.

As I was making approximately two dollars and zero cents per annum, the only place I could really afford to shop without parental support were the sort of soulless mall brand retailers that littered midtown and the less desirable stretches of Broadway in SoHo. I resembled a sort of cheap imitation of how a Banana Republic marketing team imagines yuppie architects to look, slaving all day over blueprints in sensible loafers and genuine leather belts, cups of colored pens splayed just so on slanted drawing tables. Except replace “blueprints” with “boss’ travel schedule” and “drawing tables” with “cubicle lodged between the bathroom and the mail room.” Me and my striped button downs knew when everyone picked up their copies of USA Today and when they went number two.

But I’ll be damned if the thing that excited me most about moving to another agency wasn’t the option of actually wearing jeans.

Instead of a strict dress code serving to remove distractions so I could focus on the task at hand, as people argue elementary school uniforms eliminate unnecessary diversions for school children, the manacles of my business casual dress code actually distracted me more than anything else—imagine fidgeting with the cuff of your pants, bitter about your dry cleaning bill. I never wanted to wear this shit in real life, at least not every single day, and it made my already grumpy demeanor even grumpier. I was Walter Matthau in a J. Crew merino wool v-neck.

After a while, I sucked it up and stopped being a whiny bastard, and subsequent raises afforded me some other retail options that were less restrictive to my own style. But I’ll be damned if the thing that excited me most about moving to another agency wasn’t the option of actually wearing jeans.

I don’t need to tell you all, as readers of Four Pins, that how you dress is important. Not only because of how it shapes others’ perception of you, but also because of how it makes you feel about yourself. Fuck what other people think of my current wardrobe of crew necks, jeans and sneakers, man—if I don’t feel like I look good, then I don’t feel good. And all the khakis in the world can’t help me then.

Steve Dool is a writer based in New York City. Follow him on Twitter.