One of my best friends has a son who works at J.Crew. My son has a summer job driving the trash truck to the dump and he shops at Goodwill. But I think I’ve figured it out. It’s genetic. The why I mean. The why of why I dressed like an idiot until buying a few suits and working as a CPA at the age of twenty-eight. Before then I was like Steven Wright in his story of meeting a beautiful girl at the department store, “I met this wonderful girl at Macy’s. She was buying clothes and I was putting Slinkies on the escalator.”

Escalators are more interesting than buying clothes at Macy’s, but my youthful rebellion pales compared to that of my son. His youthful defiance by expressions of sartorial deconstruction bypasses Slinkies and detours to the local thrift store buying freshly out of style duds at the price of dirt.

Here’s what John Waters, the director of the 1988 movie, Hairspray, says about fashion tips for men. (It’s as if Mr. Waters crawled into my son’s closet, took a quick picture of the dissonant display of cotton, wool and leather, then wrote this paragraph)

“You don’t need fashion designers when you are young. Have faith in your own bad taste. Buy the cheapest thing in your local thrift shop — the clothes that are freshly out of style with even the hippest people a few years older than you. Get on the fashion nerves of your peers, not your parents — that is the key to fashion leadership. Ill-fitting is always stylish. But be more creative — wear your clothes inside out, backward, upside down. Throw bleach in a load of colored laundry. Follow the exact opposite of the dry cleaning instructions inside the clothes that cost the most in your thrift shop. Don’t wear jewelry — stick Band-Aids on your wrists or make a necklace out of them. Wear Scotch tape on the side of your face like a bad face-life attempt. Mismatch your shoes…go to the thrift store the day after Halloween, when the children’s trick-or-treat costumes are on sale, buy one, and wear it as your uniform of defiance.”

Mr. Waters was sitting on Brandon’s left shoulder in every Goodwill store he entered screaming into his ear, “Ill-fitting is always stylish,” and I was on the right shoulder whispering clichés about tucking in shirts as we pushed open the glass doors of Kohl’s and breathed deeply the fragrance of mass retail.

I whispered, “Hey, Brandon, how about this pair of Bass Weejun Loafers in basic black? You can keep spare change on top of your shoes!”, while the devil Waters replied, “Go ahead, look like your Father, I won’t say a word…won’t have to…the penny loafers will scream it out like a hobo sitting court side at a Lakers game.”

Brandon’s Grandfather Terrel and Great-Grandfather Ross resorting to traditional style

Here’s what I think, which isn’t much, about clothing and young men.
Young guys eventually want to look like their Father’s, not the Dunlap belly, but when they were flat bellied twenty-somethings, sleek and young and Cary Grantish.

Guys seek solidarity with peers by avoiding traditional apparel and conversely, guys search for distinction by embracing the offbeat. They want it both ways. They don’t want to be like anybody, but they still want to be like something. Ah the horror, how to fit in yet stand apart, how to be a generational team guy and an expressive individual with unique clothing thoughts.

And I thought it was only me he was trying to not look like. No, it’s everybody.

So how do you look like nobody else yet still fit the definition of well-dressed?

In the words of Jean-Claude, the French pea of Veggie Tales fame in the castle scene (stolen from Monty Python) while expressing incredulity at their ability to clap hands when they had none (they were peas after all), “I have no idea.”

Cary Grant, however, does have an idea. The actor wrote an article for This Week magazine in 1967, discussing the finer points of men’s fashion. Here are a few of Mr. Grant’s tips:
“I’ve purchased dozens of suits over the years and they all have one attribute in common: they are in the middle of fashion… In other words, the lapels are neither too wide nor too narrow, the trousers neither too tight nor too loose, the coats neither too short nor too long.”

“It’s better to buy one good pair of shoes than four cheap ones… The same applies to suits, so permit me to suggest you buy the best you can afford even though it means buying less.”

“How do I feel about ties? If I had only one to choose, then I think a black foulard, not too wide nor too narrow, is best, as it’s acceptable with most clothes. An expensive tie is not a luxury — the wrinkles fall out quicker and the knot will hold better.”

“Learn to dispense with accessories that don’t perform a necessary function.”

“Do see that your socks stay up. Nothing can spoil an otherwise well-groomed effect like sagging socks.”

“Don’t be a snob about the way you dress. Snobbery is only a point in time. Be tolerant and helpful to the other fellow — he is yourself yesterday.”

“Wear, not only your clothes, but yourself, well, with confidence. Confidence, too, is in the middle of the road, being neither aggressiveness nor timidity. Pride of new knowledge — including knowledge of clothes — continually adds to self-confidence.”

I’m becoming Cary Grant. Naaah, I don’t look like that, nor do I dress that way, and I hate ties but I do agree with Mr. Grant’s clothing sensibility. And I no longer give apparel advice to young men. They can figure it out on their own in their own good time. Somehow, I’ve come home to roost in the sartorial nest of common sense and English decency. My son on a good clothes day