Sunday, October 19, 2025

October 19th, 2025

 Today’s quote could have come from an old soul somewhere between Steinbeck and a South Side bartender. It reminded me of something my Oldman practiced his whole life.

My Oldman knew everyone.
The banker, the lady at the dry cleaner, the cook at the diner, the overnight guy at the White Hen, most of the cops in the neighborhood, and the morning CTA guy who took our tokens. Don Shepley was always kind to the working man.
One of the men I thought about this morning was Mr. Shapiro. Bill Shapiro, my dad’s go-to salesman at the Big and Tall Shop. From the late 1960s through the early 1990s, Mr. Shapiro measured my dad’s waist and inseam, picked out his trousers and sport coats, and had his suits tailored just right.
My Oldman was a fine dresser. A mechanical engineer who spent most of his time in a draftsman’s office before finally getting his own office at the end of his career. He wore a suit to work every day; wing-tipped shoes, a square handkerchief in the pocket, cufflinks on his monogrammed shirts, and silk ties that glowed without shouting. On dress-down days, he would wear pressed khakis, a blue shirt, and a navy blazer... still with the square handkerchief, of course.
When he went to inspect railroad cars in the yards, he would show up in freshly pressed bib overalls and well-polished shit-kickers. And yes, there was still a handkerchief squared up in that pocket. The man had standards.
I remember one weekend when I was in eighth grade. I was coming up to Chicago to visit. He called my mom and told her to send me with slacks, a tie, a sport coat, and church shoes. Trouble was, nothing I had fit. My Oldman had bought us tickets to see Do Black Patent Leather Shoes Really Reflect Up? at the Candlelight Dinner Theatre down on Harlem Avenue.
When I got off the train at Union Station, the first thing he asked was, “You got your sport coat and slacks?” I told him I did, but they were too small. He came unglued, and we drove straight to Karoll’s Red Hanger, where Bill Shapiro was working at the time. Mr. Shapiro changed shops often, but always made sure my dad knew where to find him.
Looking back, I’m guessing Mr. Shapiro was gay. Though I didn’t know what gay was back then. Most men of his generation were still closeted. He was Mr. Brady gay, not Freddie Mercury gay. Back then, gay men carried themselves like British aristocrats with proper etiquette, soft voices, sharp suits. It wasn’t until disco and The Village People that the closet door swung open. Or at least that was around the time I noticed a difference.
Mr. Shapiro fitted me in a brown tweed sport coat, a tan V-neck sweater, a brown knit tie, and light brown trousers. It screamed 1979 Catholic schoolboy and he nailed it. The perfect look to attend a play about Catholic school life.
My dad wore a navy suit that night. He made sure I had a pressed square handkerchief in my new sport coat pocket. I worried we would be overdressed, but when we arrived, everyone looked sharp. After the show, we drove to White Castle and grabbed a sack of sliders. Sitting in his Cadillac at 11:30 at night, both of us in our Sunday best, eating sliders under the glow of the parking lot lights...
...that was the best.
They tore that dinner theater down in the late 1990s and replaced it with a Portillo’s and a Krispy Kreme. Maybe that is another reason that I hate both those chains. Mr. Shapiro passed around the same time. My dad and I went to his wake, both wearing suits we had bought from him.
Happy Sunday, Chalkheads. Go make friends with a stranger today. You might be surprised how astonishing that can be.