The Skinny on Jeans

Old man pants wouldn't do; I needed to get a cool pair of jeans

Photograph by Hulton Archive/Getty Images

"I thought it was Daddy standing there, when I came up the street," my mother marveled, as I trimmed a maple tree in her Connecticut front yard. The jeans I was wearing had been my father's, a Paul Newman look-alike we'd lost to cancer at 72 years young.

Mom had given me the jeans, along with two suits from when Dad moved from the factory to the office in an impressive late-in-life second act, back when she was wearing his unlaundered shirts because they still had his scent. Though I was awed and moved by how perfectly Dad's clothes fit me, I wore them that day to make Mom happy.

It was sweet, and a high compliment, that my mother mistook me for the love of her life, but it also set off alarms. I had been searching for my soul mate and didn't want to resemble a grandfather who had five kids and eight grandchildren. Dad's old man pants just wouldn't do; I needed to get a cool pair of jeans.

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I usually go to a Manhattan discount store, ask where the "normal" jeans are and hope for a sale. I don't do button fronts, which seem like a childproof-cap type safety feature for aging zipper users. Forget any pants-on-the-ground situation. And relaxed fit stresses me out.

On my inaugural shopping trip, I didn't try anything on, I was so overwhelmed by boot cut, loose, regular and classic fit options, plus something called "just below the waist," which brought to mind beer guts and plumbers' crack.

Others were ripped, bleached, embroidered, perma-wrinkled or filthy looking—like off-duty circus clowns would wear with big red shoes. I had no clue what to wear to impress a date while not trying too hard to be hip. It was certainly easier back in my father's day.

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A suited Macy's salesman offered to sell me designer jeans. Hugo Boss displayed styles named Iowa, Kansas and Montana that sounded meant for rodeo riding, though I suppose I did hope to metaphorically lasso a mate. I wondered what America's breadbasket thought about Madison Avenue's marketing. I also pondered the top $245 price tag—more than the first suit my father helped pick out for me after college.

For a guy who has run 10 marathons and is in pretty good shape, I obsessively checked my backside for jean worthiness in mirrors and store windows. Worse, I snooped the behinds of successful-looking men my age as they strutted down Broadway.

"That dude has no business wearing those 7 for All Mankind jeans," I thought. Then I saw a player with a much younger woman on his arm: "Who does he think he is, wearing Naked & Famous?" Another time simply, "Oh my God!"—embarrassed for a tragically unhip stranger.

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When I stooped to asking fashionable men who made their threads, reactions ranged from being treated like a registered sex offender to an incident at Macy's with a gentleman named Paul. Smiling, he handed me his business card.

"Call me. We'll do a shopping day," he said. I thanked him while picking up a pair of black Tommy Hilfigers—classic straight, like me.

I explained my dilemma to Angela, an adorable 20-year-old dynamo at a Greenwich Village Levi store, who should be selling hedge funds instead of hawking $30 pants.

"How 'bout these?" I asked, grabbing the closest pair.

"Oh God no!" she said. "Fantastic, she gets it," I thought.

Until Angela continued, "Someone your age would look STU-PID in skinny jeans."

Stung by her comment, but proud of my 31-inch waist, I waited for Angela to leave to sneak into a dressing room with an armful of blue youth.

In my 20s, I'd been savvy enough to avoid the stonewash debacle that friends succumbed to, but now, a huge placard touted the differences between skinny, slim and tapered that "hangs on the hip." There was even a "super skinny" version I relabeled "eating disorder," when my foot wouldn't go through the leg. One pair pushed up my junk like a male Wonderbra. I couldn't imagine leaving the dressing room clothed like an '80s porn star, though I did consider buying a pair to prowl around my apartment.

"How you doing, sir?" asked the dressing room attendant/"Levi Consultant" at another store who simultaneously fielded breaking denim crises from his associates via a wireless headphone.

"Great," I squeaked in a slim-fit, straight-legged, just-below-the-waist falsetto.

The final pair felt way weird. A glance at the tag informed me that I was modeling women's pants, which clearly exaggerated my muffin top. The dressing room mirror looked past my "bold curves" directly into my soul. I'd become Michael Scott stuck inside of an episode of "The Office."

When a woman I'd met traveling emailed that she would be in NYC for a couple of weeks, I got a second wind. On a mission for pants and passion, I returned to Macy's armed with a coupon. I found a clearance rack and when the smoke cleared, I'd spent the lavish sum of $110 on last season's Hugos. Sex sells, as does the potential for sex.

I'm still the same weight I was in high school, but have to admit that the sands of time have shifted. And although I felt guilty about the wild extravagance (being the only son of a factory worker), I paid to have my sexy jeans tapered by a real tailor.

I teach music on Saturdays and usually dress more appropriately, but one snowy day, instead of ruining nice dress pants, I wore Dad's grandpa jeans to mush to school. My first class went crazy.

"Great casual look, Mr. Prior," said a sharply dressed flutist.

A teenage fashionista in the back row cured my blues with, "Way to rock the skinny jeans."

Skinny jeans? Embarrassed—and exhilarated—by the attention, I was confused because they were just boring dungarees, like when I was a thin kid who'd gotten cut from the football team because I didn't weigh enough.

I only then remembered that Mom always took three quarters of an inch off the leg, tailoring them for Dad—like I had just paid someone to do. The normal jeans weren't for old guys, but they were perfect for a confident man who knew who he was. And I felt blessed to have my stylish father's slim genes to pull it off.