I Dressed Like Bill Belichick For A Day In Hopes Of Learning What It Feels Like to Win

This week, Deadspin and Jezebel swap beats to celebrate America’s most dangerous and controversial pastimes: football and fashion, two sports that have far more in common than you think.

NFL head coaches are not a group known for dressing well, but the worst offender in the league is Bill Belichick, a member of Donald Trump’s Council on Sport, Fitness, and Nutrition and a man who has, by his own admission, “ handled dozens of balls” in order to prove that his men are not cheaters. I’m not a Patriots fan, and Tom Brady’s propensity for strange diets and kissing his son square on the mouth leaves me cold, but something about Belichick’s game day attire has always intrigued me.

Though he coached this season’s opener against the Houston Texans in a fairly staid short-sleeved windbreaker with pants to match, the attire I associate Belichick with is sartorially confusing: a New England Patriots hoodie, transformed into a cap-sleeved sweat-tee. A long-sleeve t-shirt is worn underneath the hoodie, layered not for fashion (as I was soon to learn), but for practicality. Paired with the aforementioned wind pants, sneakers, a headset, and a Microsoft Surface tablet occasionally thrown to the sidelines in frustration, it is an arresting vision: a man dedicated to comfort, sport, and, maybe fashion?

The line between high fashion and streetwear has now blurred to an indistinguishable smear; Kim Kardashian trots through the streets of Calabasas clad in her husband’s interpretation of 1980s sportswear, and Anna Wintour, Vogue’s high priestess, has not one but two pairs of Jordans created under her tutelage. In June, designer Alexander Wang sent models down the runway in looks that are a prime example of how far athleisure has come. Belichick’s curious sartorial choices represent a shared sensibility; I, too, enjoy the comfort of a sweatshirt. I love tailoring my own clothes with nothing more than scissors and a fleeting vision; I love soft pants and dressing for either a nap or Thanksgiving dinner. In short, Belichick and I are more kindred spirits than I thought.

My challenge to myself was to dress like Bill Belichick for one day and to see if I felt powerful, stupid, athletic, or a titillating combination therein. I ordered a men’s XXL Patriots hoodie from Amazon and stopped by my local Modell’s Sporting Goods to procure a pair of pants that would approximate the look and feel of Belichick’s trouser situation. I admit that I could’ve done better in this department, but buying something that I’d actually wear again felt important. For verisimilitude, I should’ve worn sneakers, but a bad pair of shoes worn two weeks ago tore the tops of my feet to shreds, and so flip-flops were the answer. I changed in the bathroom at work when I got in, removing my dress in a stall in the bathroom and emerging catatonic with rage, in my best approximation of the Belichick I remember storming off the field after losing to the Philadelphia Eagles in the Super Bowl.

The day I chose to wear this outfit was extraordinarily warm, but thankfully the GMG offices are kept very, very cold. My core was toasty but my arms were freezing. Though not a single person looked at me strangely while I was at the office, I felt self-conscious in a way that I did not anticipate. Did everyone think I was a Patriots fan, consumed with such rabid love for my team that I emulated its coach in dress on the first day of the season? Was everyone staring at me? Was I hideous?

These questions mercifully went unanswered, but my colleagues’ reassurance that I didn’t look like an asshole buoyed my spirits. “You were walking away with the purpose of a football coach at the end of a game,” Deadspin news editor Samer Kalaf said to me in Slack. “The headset makes you look like you really have something to do at any given moment.” Jezebel’s Hazel Cills told me that she’d dump a cooler of Gatorade on me. If I hadn’t convinced myself I was owning the look, at least my coworkers believed me. But would the general public?

Luckily, I was able to see for myself on my 15-minute walk to the video studio at around 2 p.m., when the sun was at its full power. Being hot and not being able to remedy that is one of my least favorite sensations on the planet. For the blog, I persevered, though the desire to remove my sweatshirt and walk the rest of the way to the studio in my brassiere and some track pants was strong. It was at this point, about halfway through my slog, that I realized that the long-sleeved shirt worn under the sweatshirt serves a purpose beyond aesthetics: surely it must wick. Alas, the shirt I had ordered to simulate Belichick’s second layer didn’t arrive in time. A small lake of sweat collected at the small of my back, unabsorbed by the sweatshirt.

After work I met a friend for a drink at a bar. No one paid attention to me, and when the sweat pool finally evaporated, I felt at ease. Is this how Bill Belichick feels, I wondered, sitting in the locker room at halftime, screaming at his team in an apoplectic rage? Maybe cloaking his body in ultimate comfort allows him to really inhabit his passion for sport.

On my way to and from my various locations, a few men on the street shouted things at me that I didn’t quite hear—support for the New England Patriots, perhaps. A man sitting on a bench in front of a bougie cafe gave me an enthusiastic thumbs-up, accompanied by a hearty “Go Pats!” that I gamely returned with a smile. Every time someone commented, I felt like clarifying immediately that I wasn’t serious, but that impulse died as I continued my walk in the oppressive heat. What did it matter? Really, who cares? Dressing like a man whose sole focus is winning didn’t make me feel like I was more focused on winning than I am every day, but at least I was (slightly) comfortable.