The young man of promise wore wingtips

A pair of shoes can walk you back in time.

About three times a year I haul all my dress shoes out of the closet for an hour-long polishing and shining session. I wear dress shoes maybe twice a week now. For 30 years though I wore them pretty much every work day. And a lot of weekends. Now I get by with a couple of pairs of penny loafers, a tassel loafer, and a pair of cowboy boots I’ve had for at least 20 years.

Then there’s my wing tips. They’re too narrow now. Twenty five years of running has widened my feet. The sewing is slightly frayed here and there. And on one of them, the upper is starting to crack. Yet I can’t bring myself to throw them out.

Life, if you’re lucky, is a long race. I’m at about the 20-mile mark in my marathon. Marathoners will know what I mean. The final 6.2 miles can be a joy or a horrible slog. It depends on both your preparation and your luck. It’s the point you start thinking about the finish line and how you’ll do when you cross it.

The wingtips represent my miles, oh, maybe 9 through 17. You’re past youth and education. You stride the miles strong and confident.

I bought these shoes at Lord & Taylor in Copley Square, Boston, sometime in the early 1980s. The company I worked for (Cahners Publishing disappeared years ago) had a culture of conservative suits and shoes. When I joined in 1980 for the princely sum of $16,500 per year, I and my cohorts would buy suits at store called Simon & Sons. It sold cheap suits but in a nice setting, with elderly salesmen treating you as if you were buying a bespoke Brioni. As you moved up the ranks — and I did — you’d graduate to Jos. A. Banks. In those days Banks manufactured its own suits and distributed then directly to its stores. It was in my Banks days that I added these nicely-made wingtips. I probably had them on when I purchased my first Brooks Brothers suit.

The shoes represent the apogee of my work life and ambition. I was supervising people, going to off-site management meetings, viewed by management as destined for bigger things. I had an offer somewhere else and Cahners gave me a big raise and a company car. The executives all had Mont Blanc ballpoint pens. On a trip home from Europe I bought a Mont Blanc ballpoint pen off the Lufthansa duty-free cart. It cost $50. After one promotion, my wife bought me the matching mechanical pencil.

Some time in that period my mother presented me with a six-pair pack of Gold Toe over-the-calf socks. My dad never wore them, but mom felt a man on the rise should wear over-the-calf socks. I still wouldn’t be caught dead in a suit and dress shoes without black, over-the-calf socks. I’m not sure young men today realize how awful those garish, color-patterned socks look. Especially with brown shoes and a blue suit — the puerilization of the American male.

Time passes. At one corporate review, I had passed 30-years old. The consultant, a man in his 80s but still sharp as a tack, joked, “You’re no longer a young man of promise. Now you gotta produce!”

I produced, but never quite made VP at Cahners. My one regret is never having received a pair of Cahners cufflinks that would have accompanied that promotion. I did make the title of executive vice president at the company to which Cahners sold the property I worked on. But no more company car, much less cufflinks. Then the subsequent company sold the properties I helped oversee. I got a nice buyout and switched careers. That was a dozen years ago, and I don’t think I’ve worn the wingtips since.

A seeming lifetime has passed since I acquired those shoes. Just holding them, dusty from disuse in the closet, brings a tide of memories. I don’t like to spend too much time dwelling on the past. A character in a James Michener novel remarked that if you mine your memories too early, you’ll be tapped out by the time you really need them. But hefting a pair of shoes can momentarily bring back all of the triumphs and struggles of a career, the wins and losses, the opportunities taken and the ones that got away.

After polishing them as best I could, I put on a pair of dress socks and tried them on. Still wearable, if a bit tight. But they show their wear. My mom, if dementia hadn’t robbed her of comprehension, would have counseled me to shelve those old shoes for good. What young man of promise would go around in worn shoes?

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