By Greg Dawson

Before reading further, study the photo of the four men. They are, left to right, actor Tom Nowicki, former U.S. poet laureate Billy Collins, Winter Park Magazine editor and publisher Randy Noles, and Rollins College English instructor Mike McLeod. 

I took the picture. Trust me, I would have blended right in with this motley crew.

We represent the sartorial incorrectness that Craig DeLongy has spent decades striving to reverse as founder of John Craig Clothier on Park Avenue, purveyor of fine menswear. DeLongy was named 2023 Merchant of the Year, Specialty Store, by New York-based MR Magazine.

Speaking with DeLongy in his office above the store, I showed him the photo on my iPhone and was surprised by his restrained critique.

“Randy needs help, so does the guy in the floral shirt,” he noted. “I’m not a fan of floral shirts — a little outdated. I’d venture to say he’s had that shirt for a long time. The other two aren’t that bad. Four guys out having lunch — it really doesn’t matter.” 

When I told him that it wasn’t lunch, it was dinner, and it was at the posh Alfond Inn, then it mattered. I asked if he would ever show up at the Alfond dressed like that. DeLongy recoiled, as if from an awful smell: 

“Oh, no. No. I wouldn’t be washing my car in a couple of these outfits. But that’s me.”

That is DeLongy, unvarnished, and exactly why I was there — hoping that he could shed light on a stereotype that’s 100 percent true: The vast majority of men are fashion zombies, marching blindly, blithely ahead in hideous ill-fitting garb that’s caused generations of women to ask: “Is that what you’re wearing?”

Translation: That’s not what you’re wearing, not if you expect me to be seen with you in public.

The day we met, DeLongy was slumming by his standards in jeans and a quarter-zip over an open-collar, long-sleeved shirt. He semi-apologized: “I’m the guy who goes to Publix always wearing a sport coat. My wife often says, ‘Do you have to wear a sport coat every day?’ And I say, ‘Yeah, I do.’ I’m dressed casual today because we’re going to the warehouse.”

DeLongy’s folksy manner and faint Kansas twang from boyhood belie the fervor and frustration of a sartorial evangelist under a self-imposed gag order:

“I’d seen pictures of a very prominent local woman and her children and husband at Easter. I wanted to walk up to her and say, ‘Send your husband in. We need to shorten his sleeves, we need to tuck in his shirttail and we need to shorten his pants.’ It would have made a world of difference in the way he looked. But I chose not to mention it. I’m very careful. I don’t want to embarrass anybody.”

DeLongy continued: “I’ll see a woman all dressed up, accessories and a beautiful purse, and the man looks like he just walked out of a Tommy Bahama store. I’m going, ‘He doesn’t get it.’”

And I’m going, “Tommy Bahama is a bad thing?” But DeLongy was just getting started: “On Instagram, I saw a Palm Beach couple talking about what they were wearing. The guy was wearing all-custom out of Italy, but he killed it by wearing a crew-neck T-shirt instead of a V-neck. And I actually commented on this. I said, ‘Why do men do this?’”

I shook my head as if in dismay and wondered if DeLongy could tell that I was desperately trying to feign the sharing of his pain. My wardrobe is to haute couture what Velveeta is to haute cuisine.

Is knowing how to dress well nature or nurture? In DeLongy’s case, maybe both. “My mother started dressing me when I was a little boy,” he said. “She sent me off to high school wearing black-and-white saddle oxfords. I barely escaped that day.”

He was even luckier to escape the day he was on a street corner in Manhattan and noticed the man in front of him in a sport coat with double-side vents that were still stitched together. “I see this all the time,” he sighed.

DeLongy boldly intervened: “Excuse me, I’m in the men’s clothing business. Would you mind if I fixed your jacket? He said, ‘Nah, I wouldn’t mind.’ So I reached into my pocket and popped out my knife, cut the threads and said, ‘There you go!’ He was very happy with my little alteration.”

There are two types for men who dress well, DeLongy said: “There’s the man who gets it, who knows what he wants to wear, with our assistance. The other is being directed by his spouse. Unfortunately, there’s a third type who just doesn’t care. He might be wearing a white button-down shirt, khaki pants and an old navy blazer and thinking he’s just fine.”

Except for the blazer that’s basically the way I reported for work every day for five decades, and no one ever told me it wasn’t fine. Of course, we were reporters and didn’t know any better. Plus, for me and my colleagues, khakis were an integral part of the newsroom uniform.

Still, in 50 years of marriage, my wife, Candy, has managed to teach the old dog a few new fashion tricks. But I still get that familiar “is that what you’re wearing” question on those occasions when I choose something insanely wrong. Maybe it’s an unconscious protest and homage to a fallen favorite garment.

I once had a light jacket that I loved. It was made of a canvas-like material the color of effluent, fit like a large sack and had floppy Captain Kangaroo pockets ideal for carrying everything from car keys to snacks and Kleenex. 

Over the years it had picked up a few stains. For some reason, Candy detested the jacket. One day, like Jimmy Hoffa, it mysteriously vanished. She denies it, but to this day I believe that Candy buried it in the backyard. The old dog is still in mourning.

Greg Dawson is a journalist and author. He has worked as a reporter, a television critic, a metro columnist and consumer columnist. His most recent book, with Susan Hood, is Alias Anna: A True Story of Outwitting the Nazis (HarperCollins, 2022). Dawson is a contributing writer for Winter Park Magazine.

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