My Cap Tip to the Times

By Joseph Kellard


So there I was this morning, sitting in a Starbucks with an iced green tea in one hand and a New York Times in the other, wearing my driving cap, when I came across an article in the Styles section on the growing popularity of the driving cap. The article opens with the observation that more men seem to be doffing their baseball caps for the stylish driving cap.

“Many men have taken to the far worthier wool driving cap, and with good reason. It may not suggest that you are an indie-rock guitar rebel who thinks two chords are plenty, but it will keep your head warmer — and more important, your hair neater — in cold weather.”

Last year I decided it was time to find another style of headwear rather than my favorite but aging Yankees baseball cap and my tight-fitting wool skull cap for when the mercury goes way south. Actually, I had started my hunt for a driving cap in 2007, after I saw the every-stylish Tom Brady, the “Golden Boy” quarterback for the New England Patriots, wear one after a post-game press conference. Now, I’d always associated the driving cap with my Uncle Dan, an Italian immigrant and World War I veteran, which he often wore, as well as with old, white New York City cab drivers from decades past. But on Brady made the cap looked stylish, and that’s what a Super Bowl-winning quarterback with model good looks can do: sell cool.

I shopped around, and it took me bit of time to find just the right cap. I originally bought a brown, plaid-patterned cap that turned out to be oversized, flaring out to make me look like a 1930s newsboy selling papers on a city street corner, as alluded to in the Times article, or a hip-hop rapper, definitely a false advertisement. So I hung it up, searched some more, and found a smaller, slate gray cap at Banana Republic, which framed my face just right and that I could tilt to the side to add a bit of flare.

“Many men, drawn to the cap’s misty English gentry connotations, opt for plaids or tweeds of a colorful stripe, for some country-squire pizzazz. But its background is squarely 19th-century working class, when they were such common garb as to be known simply as caps. (The 20th-century desire to upgrade its status can be seen in the name “driving cap,” as well as its aliases: ‘ivy cap’ or ‘golf cap.’) In a humbler-looking fabric, like a gray or brown herringbone, a plain loden or a lightly speckled tweed, the cap looks great with a peacoat, leather jacket or fisherman’s sweater — or anything one might deem more Irish than squirish.”

I’m on the hunt again for another driving cap, like the one pictured in the Times article. If you find one, especially at a cheaper price, let me know. If you do, I’ll tip my cap to you.