Illustration by Mr Seth Armstrong

EPISODE 23: making the rounds

Unlike drinking, shopping is an activity I prefer to do alone. The thought of catwalking out of a department store dressing room to an audience of my guy friends, and saying, "So what do you fellas think?" is just not on. Long ago I abandoned my Carrie Bradshaw dreams of hitting the stores and then adjourning for cocktails, fist bumps and wry apercus such as "Dude, you crushed it when you spotted the Michael Bastian at 40% off!" I wouldn't go for a massage with a wingman. I wouldn't go to the barber with one either, so when it comes to shopping, I genuinely believe: he who travels swiftest travels alone.

The exception to the rule is when I bring my son along. If Nicholas were a budding Charles Darwin, we'd spend cold, wet Saturday mornings admiring stuffed wildebeest in the Museum of Natural History. But he's not. A few weeks ago, I asked him what he wanted for his eighth birthday present. I expected him to say, "a dog".

Instead he replied, "I'd like a tuxedo."

"A tuxedo? And where will you be wearing this tuxedo?"

"Out to dinner," Nicholas said as if he were a regular at El Morocco.

"You're not getting a tuxedo. OK? You have to be fully grown... I was at least 15 before I owned my first set of dinner clothes, and that set came from a thrift shop."

Nicholas seems to have inherited my gene for being the blind pig that somehow sniffs out the most luxurious item in any shop

The heir would not take no for an answer. "OK, then what about a suit?" he asked. We eventually reached a compromise. He already owned a pair of seersucker trousers, so we decided his birthday present would be the jacket to match. I had a few items I needed to add to my spring wardrobe - notably a new pair of dress shoes. So on a recent Saturday morning, we headed off to Leffot for me and Crewcuts for him.

"Dad, this place is like a museum. A museum of shoes," Nicholas said as we stepped out of a West Village drizzle and into Leffot, New York's best men's shoe shop. Nicholas' description wasn't far off. Leffot looks more like an art gallery than a boutique. The walls are black. A chandelier hangs from the ceiling, and the shop's centerpiece is a long blond wood table where the owner, Steven Taffel, displays tightly curated rows of his favourite shoemakers. Solid English brogues from Edward Green sit alongside dress leather boots from Ron Rider, the artisanal American bootmaker.

With this smorgasbord of high-end footwear laid out before him, I was curious to see what style and shoemaker Nicholas' little heart would be drawn to. I had given him the basic brief on the taxi ride downtown: "I'm thinking of getting a two-eyelet lace-up in brown. Something I could use to dress down a suit or dress up a pair of khakis." That mission statement went right out the window, as he seems to have inherited my gene for being the blind pig that somehow sniffs out the most luxurious item in any shop.

"What about these?" he said as he held up a sleek black pair of lace-ups with lines reminiscent of a vintage Bugatti. The shoes were the handiwork of Pierre Corthay, the Frenchman who trained at John Lobb and ran Berluti's atelier before striking out on his own in 1990. "You should get black, Dad. You have so many brown shoes and like only one black pair." When I waved him off, Nicholas tried to push me into a pair of monk-strap loafers, then a Chelsea boot, and then a python-skinned pair of lace-ups that looked as if they were on loan from Joe Jackson circa Look Sharp!.

Like all great merchants Steve takes the measure of the man, not just his shoe size, so he gently steered Nicholas and I away from the super-pricey Corthays in favour of a more modest pair of Alfred Sargent suede bluchers. Members of the Sargent family have been making shoes in Northampton for more than 100 years, and they are in my sweet spot. When I asked Steven whether the Sargents came in a tobacco rather than a dark brown, he offered to order me a pair. As we finalised the specs of my order, Nicholas reminded me that he was not just my acolyte, but he had his own errands to run.

Nicholas tried to push me into a pair of python-skinned lace-ups that looked as if they were on loan from Joe Jackson circa Look Sharp!

"Dad, are we almost done here?"

Watching him fidget in his navy blue duffle coat, I was reminded of the same tension I felt with my father on similarly one-sided expeditions. By the time I was 10 years old, I could have given a dissertation on the various Manhattan men's stores of the 1970s. Back then, a Saturday with my dad consisted of him "making the rounds" before we "hit the flicks". Whenever my dad went into the fitting room, I can remember tightening up with worry that we'd arrive too late for the 3pm showing of the latest Richard Pryor comedy or Burt Reynolds actioner.

Dad's rounds were all within a tight radius of Madison Avenue and 44th Street, and the stores included Brooks Brothers; the slightly cooler and pricier Paul Stuart; J. Press (hardcore Ivy League), and Chipp, which I had a hard time distinguishing from J. Press. There was also Abercrombie & Fitch, which back then was not a teen disco for the chiselled, but a purveyor of field clothes for the paunchy. It was a bright spot as it had its own gun department and a miniature submarine for sale.

My dad was a banker and more conservative in his taste than my boyhood self. I always encouraged him to shop at Paul Stuart, the hippest of the bunch where he tended to browse then buy at Brooks Brothers. Indeed, when I was in my twenties and finally had a few of my own dollars in my pocket, I met him for dinner in my first pair of English bench-made lace-ups that I had purchased at Paul Stuart. He looked at my grey suit and brown shoes before quipping, "Nice booties". I could never tell whether the remark was an accolade or a put-down. Now I suspect it was both.

When Nicholas and I finally arrived at Crewcuts, we were in luck as the spring stock had just arrived and his seersucker blazer was there. He allowed me to play Mr Bates to his Lord Grantham and help him on with a size seven followed by a size eight. He likes a snug, Thom Browne-esque fit while I prefer seersucker to hang loose, as if you're some dissolute newspaperman or civil rights lawyer. Besides, Nicholas is still a growing boy and I make him get things big so he does not burn through them in a few weeks time. As we stepped into a taxi for the ride home after a successful man-date, I asked Nicholas about whether he preferred shopping with his mother or me. "You know you're the best, Dad, but why did we spend soooo much time looking for your shoes and soooo little time on my jacket?"

Perhaps I'll return to shopping alone.

To read Mr Brodie's previous columns, click here. Follow Mr Brodie on Twitter @jbrodieny

Timely Style Staples

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