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N Sync wearing regrettable vests Photo: Ron Gaiella/Getty Images

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The Road to Style Is Paved With Regrettable Vests

A journey of sleeveless self-discovery.

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“Wait ... you had a vest phase?”

My girlfriend nearly spit out her calamari when she found out that I had enjoyed quite the love affair with those notorious sleeveless numbers through my college years in Syracuse. We’d only been dating a few months and this was the most scandalous secret I had revealed.

The shock did not end there. She was further dismayed to learn that I did not mean vests of the puffy, sporty variety (marginally acceptable, if marred by their own problematic connotations), but black, dressy suit vests worn sans blazer over a button-down with dark jeans. It was my go-to outfit every time I went out for a night on the town. In retrospect, I probably looked like an amateur magician.

“You should really throw them out,” my girlfriend advised, dead serious.

Now, I have always considered myself to be above-average fashionable, especially for a suburban-raised straight white male. I have a deep appreciation for layering, wear jeans that actually fit, and know that the shoes make the outfit (not sneakers). But nobody is born dressing like Tom Ford. My long and tumultuous road to moderately good fashion sense involved an ill-advised obsession with Justin Timberlake, a healthy dose of teen pretension, and, yes, four (very) regrettable vests. This is the story of how each one of those vests (all still sitting in my closet) helped lead me to fashion enlightenment.

1. The Gateway Vest

I am 14, just entering high school, and don’t particularly consider the clothes on my body much at all beyond how funny that day’s graphic tee is to my friends (I definitely have a “Vote for Pedro” shirt). But it’s also 2006 and at that very same moment in time a child star-turned-mature pop icon named Justin Timberlake is “bringing sexy back.” I’m barely old enough to even know what sexy is, much less where it’s been the past few years, but I know that I want it.

Of course, this is all happening as the standard self-consciousness and insecurities of my age are setting in and taking hold. Courting members of the opposite sex is suddenly less dependent on how fast I can run at recess and more so about these pesky things called “appearance” and “confidence.”

Timberlake is culturally ubiquitous at this point, but I am more properly introduced to the man’s music by my mother, who at the age of 44 buys FutureSex/LoveSounds on CD for herself (she was a big Justified fan) and blasts it in the car while driving me to school every morning. It doesn’t quite jive with the classic rock sensibility my dad has instilled in me (I am pretty much a grunge geek at this point, increasingly obsessed with Nirvana), but I can not deny its cool (or those seductive beats). Oh, and the ladies love it! I see videos of him performing live with girls swooning and screaming for his smooth dance moves.

I hone in on JT’s clothes. My mother is a sharply-dressed and trendy woman who regularly mocks my dad’s ill-fitting wardrobe and John Deere chic. This is clarifying for me and I begin to subconsciously model my vision of cool off Timberlake’s outfits. And this, for better or worse, is how the vest becomes, for me, the ultimate totem of cool; the secret weapon of a man who knows how to party, but still dresses with class.

My mom soon relents to my begging, and at the Express in Delaware’s Christiana Mall, she buys me a black wool pinstripe vest with buttons. Where will I be wearing this? Good question. But this vest makes me cool. I imagine it will work like the sneakers in Like Mike and transform me overnight into a phenomenal dancer. Girls will soon be fawning. I am in love.

2. The I-Should-Probably-Stop-Looking-Like-I’m-Perpetually-at-Prom Vest

I am 16 now and, though it is still my most prized article of clothing, I have worn my Express vest exactly two times. The problem, of course, is that I have literally no occasion to bust it out. I’m 16! My fancy date nights out are few and far between. This is also the first two-year span in my lifetime that nobody in my giant Italian family gets married, leaving me with no formal events on my calendar. Am I supposed to wear a vest to the movie theater?

When I do vest up, it’s nothing short of a goddamn mess. For an April high school dance with my new girlfriend, I don my pinstripe vest over a white striped shirt, not bothering with a jacket, even though my suit vest basically demands it.

Stripes on stripes and wool in the spring. I should be in prison.

The one thing I have going for me at this time is that my jeans game is strong. My mom has introduced me to the joys of designer jeans (Express and Lucky, specifically) and I take a perverse pride in flaunting my high-brow taste over my Wrangler-clad friends.

I’m becoming slightly more aware of all the errors of my ways, but I am not ready to give up on vests just yet. My modest compromise is that perhaps any material other than wool would help to dial down my pretentiousness — I can’t always look like I’m at prom. So I return to the mall, this time walking away with an Alfani black polyester vest. It is still far too formal, but without the wool and sharp pinstripes I do look slightly less like a newspaper boy from the ‘30s. This baby gets me through another two years of high school dances (I still have no other place to wear it).

3. The “Casual” Vest

It takes me three more years to realize that I just cannot make suit vests work... without a suit. But I’m in college now, and I finally have reasons to look nice. After all, one must look dapper for blackout nights dancing on sticky basement floors.

Like most college kids, I am in a race to fully express myself and leave my mark on the world. I need a statement piece that says “I’m classy, but I don’t take myself too seriously; I’m trendy, but not a style sheep.”

I don’t immediately realize the statement piece I’m looking for is a statement vest. But fate strikes on a winter break trip to the Guess outlet when I spot a charcoal asymmetrical-cut zippered vest with even MORE zippers on the pockets. It might as well be a superhero cape. I fork over $75 without thinking.

This asymmetrical monstrosity becomes the centerpiece of my signature outfit: my new vest over a dark blue Banana Republic button-down, Lucky bootcut jeans, and black leather boots. I wear this exact ensemble out enough times to warrant a role in a Wes Anderson movie. And I think I look good. Damn good.

But everybody thinks they look good in college. And besides, in Syracuse, fashion is irrelevant because every outfit is buried beneath giant North Face coats and scarves. A subsequent semester in Los Angeles, interning on the Universal Studios lot, forces me to get real when it comes to dressing. I need to look both fashion-forward and professional and I begin to consider how every part of an outfit works together. No vest is an island.

4. The Puffy Vest of Quiet Resignation

I am 24 now. There is only one vest in my wardrobe rotation. It is a puffy nylon sport vest with a fleece hood. It’s as basic as it gets. I wear it on brisk fall days when my chest is ever so slightly chilly, but my arms are breaking out in a sweat.

The ridicule of multiple girlfriends has shamed the rest of my sleeveless repertoire to the back of my closet. While my high school sweetheart and fellow pretentious teen may have found my vest-wearing endearing, it became a problem in later relationships, especially my bougie post-grad girlfriend who pulled the nauseatingly cliché (but also educational) move of personally making over my wardrobe with her parents’ formidable credit card. My vests were not part of her plan.

Even without that not-so-gentle pushing, it occurred to me that in all my years of stubbornly stumping the vest in public, rarely did I ever see any of my peers doing the same. In fact, the only people I actually do see vesting up in New York, where I live now, are older, more well-off, model-caliber men with $1,000 pants and shoes and shirts and watches and jackets to match.

In the decade I have spent becoming more fashion conscious, my shoes have gotten nicer, my clothes better-fitting, my sense of matching more creative and my taste more refined. But vests and the suave men who wear them seem as inaccessible to me now as JT did to my 14-year-old self in high school. Sometimes I wonder if I’ll ever be able to pull them off; don’t we all have a vest of a some kind in our lives?

Fashion is so often aspirational (“Dress for the job you want, not the one you’ve got”), but I’ve come to find that the outfits that truly work are never forced. They are a reflection of your own unique creativity and comfort level. The problem is I never figured out how to own my vests. I was just wearing a costume. I am not a male model, or a socialite frequenting Michelin-star lunch cafés, or a pop star hanging out at the VMAs. I am not a magician.

These days, vests are something I admire from afar, the same way my current girlfriend knows that she can probably never pull off that sparkling orange halter top Rihanna rocked at the Grammys.

But lucky for me… vests don’t have sleeves. And that means I can still squeeze my conveniently thin frame into every one I’ve ever owned. So they’ll remain in my closet, no matter how many times my girlfriend objects. Someday, I might just need them.


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