Family Cruise: Joe on Style

HONG KONG – I'm standing in Baron Kay's Tailors witnessing something I never thought I'd see: my son being fitted for custom dress shirts. This is the boy whose prized article of clothing is a pair of never-washed jeans with an embroidered skull on the thigh. This is the boy who honestly asked if a "hoodie" was acceptable cruise wear. Indeed, I spent more time helping him shop for appropriate clothes for this luxury adventure (a total of 31 formal nights) than I did for myself.

But I remember feeling the same way about style when I was young. I remember wincing when my mother combed my freshly greased hair into a flip curl. I remember arguing with my father about why I needed to know how to tie a necktie when there was such a convenience as a clip-on. I also remember the few times I tried to be stylish – most notably the peach, three-piece corduroy suit I wore to my junior prom.

Style has to be one of the most difficult things for a father to teach a son, mainly because the father's style is never the son's. Specific tastes change too much between generations to be passed along.

Paul's is the generation of low-riding, baggy pants, hiked-up boxers, and weight-lifter undershirts. I want him to feel how clothes—the right clothes—can transform him, and how he can use style to separate himself from the tens of thousands of other college graduates in the job market. I'd like him to see how to not only wear smart clothes, but also, to feel smart in them. And of course, looking good is often the first tentative step toward realizing pride, love, and of course, success.

The most money I ever spent on an article of clothing was when I purchased a tuxedo from Kilgore on London's Savile Row. The salesman noticed me agonizing over the four-figure price and said both frankly and somewhat pitifully: "Don't worry sir. It is an investment that will see you out." I asked if he meant what I thought he meant, that this tux would wear so well I could be buried in it. He nodded demurely. As I'm an amortizing sort, that promise cinched the deal. I bought it, and I'm glad I did. That tux fits me so well, and I feel so stately in it, that I stand taller and occasionally even rise above myself. I wanted Paul to experience that same feeling.

"What style collar would you prefer, young sir?" asks the clerk at Baron Kay's, displaying six different options. Next in line are decisions about cuffs, buttons, tapering, and monograms. At one point, my bewildered son actually mumbles "It doesn't matter," and the clerk bristles.

Isn't that the point? Isn't that the whole lesson I'm trying to convey? This does matter. Clothes make the man, just as surely as these men make the clothes.

Paul remains skeptical, but relents. It's my money, not his, so what's the difference? That is, until a few evenings later when we're at a cocktail party in the Palm Court and a beautiful young lady drifts by in her evening wear and whispers two words: "Nice shirt.”