Fashion Masochist: The Jarty

HEAD-TO-TOE DENIM HAS BEEN A SERIOUS FASHION no-no ever since John Mellencamp dropped the Cougar, Tiffany dropped the mall tours, and George Michael dropped Andrew Ridgeley. A relic of the '80s and early '90s, the "jarty" (jean + party) was eclipsed in popularity only by pirates and "G.I. Joes and Barbie Hos" in the kegger-theme playbook of my college days.

Now, more than two decades post-Wham!, the jarty is staging a comeback, as the stylish likes of Penélope Cruz, Alicia Keys, Christina Ricci, and Kanye West have unapologetically broken out the so-called Canadian Tuxedo (also known as the New Jersey Tuxedo, the Farmer's Pajamas, and—my favorite—the Redneck Tracksuit). In fact, it was a jarty all over the runway at the latest fashion show for William Rast, Justin Timberlake's clothing line.

Bringing sexy back may have been a prescient call. But reviving matching denim? Far murkier territory. To test the blue-on-blue waters myself, I assemble a rotation of denim pieces—short-sleeved shirt, long-sleeved shirt, slouchy jeans, tight jeans, classic jacket, and vest—and choose a Casual Friday to ease into my planned five-day experiment. When I arrive at the office in an indigo shirt-jeans combo prepared for Kelly Kapowski references, I receive but a single curious "Double denim? Huh..." from a nostalgic older coworker. Similarly, a friend mentions that my outfit makes me look young—probably because she hasn't double-dipped denim since her own youth.

By Monday, I'm thrilled that my assignment gives me an excuse to keep on doing the jean thing in the office and beyond. Though it might have gone differently if paired with a baseball cap and blinding white tenni-pumps, the denim extravaganza continues to please, no matter which items I pick from my selection. The vibe is a relaxed but confident I know the rules, and I choose to break the rules. Plus, everything matches, so getting dressed in the morning is a breeze.

Problem is, I can't tear myself away from the jarty's freedom and ease and just-realized coolness. For days after my official test drive ends, the denim uniform stays—like last Friday's beyond-flat keg that a frat boy persists in swigging into the school week. My laundry habits also evoke that frat boy: I'm so addicted to the fantastically cowgirly long-sleeved denim shirt that I'd rather wear it slightly soiled day after day than give it a wash break.

After more than a week of denim madness, the same friend who originally praised me for my youthful look stages an intervention. "How much longer are you planning to wear that?" she asks, perhaps tipped off by the fragrance. "I'm still researching," I reply unconvincingly. Then to the laundry my denim goes. But when it gets back, life is a jarty again.