Alan S. Oser

After I retired, I began to wear a peaked cap. And not just any old peaked cap.

In winter it must be a woolen Borsalino cap, from Italy, and in the spring and fall it must be a Bailey of Hollywood linen cap. I buy them from Samuel’s Hats, on Nassau Street near John Street in Manhattan. Samuel has sold hats for 20 years in three locations downtown, arriving on John Street in 1999. It pleases me to buy clothes from a small proprietor-run store that has been around a long time, especially when I can deal directly with the owner.

I used to wear fedoras, but retirement required a change in hats. An entire new wardrobe, in fact. The cessation of daily employment seems to have changed my approach to clothing. It needs to express the retired me.

Samuel Castro, of Samuel's Hats,
long in downtown Manhattan, NYC

As a white-collar worker, a cap was not “me.” Neither was a sport shirt without a tie, or the loafers I have started wearing without regard to the sensitivities of my feet. However, to the extent that the cap is handsome, the shirt purchased at an unforgivable price from an Orvis catalogue, and the loafers spiffy if uncomfortable, the post-retirement outfit tries to make a good impression, just as the work wardrobe did

The working professional wants the public to believe that he is a serious person with financial resources, and therefore, possibly, of other resources. He cares about first impressions. The sloppily dressed man makes himself vulnerable to unfavorable conclusions about his personal qualities. The well-dressed man is a step ahead until foolish words betray him. Ditto the well-dressed woman. (A different line of reasoning applies to artists, musicians, sculptors and other creative persons, so exclude them from these generalizations.)

The retiree faces a different situation. The retiree must rely on gray hair and a pleasant manner, rather than attire, to put himself a step ahead on first impression. Clothing must complement senior status. To be elderly and no longer working, and yet to be formally turned out, seems a contradiction in terms. It does not work to one’s advantage.

Here is an imaginary conversation I expect to have some day if a well-dressed young man sits next to me on a shuttle flight to Washington (if I take a shuttle flight to Washington, which is not likely). It goes like this:

Young Man: “I admire your outfit, Sir.”

Me: “Why, thank you. You don’t look so bad yourself. I notice you wear a suit and tie. I once did myself, but not since I retired and my manner turned pleasant.”

Y.M.: “I envy you, Sir. If I dressed in casual clothes no one would take me seriously. But you don’t have to worry about that. People will respect you even if you don’t wear a tie.”

Me: “It’s true. The gray hair helps too. But you seem pleasant, the buttoned-down collar notwithstanding.”

“Oh no sir. You mistake my personality. Actually I’m seething over something my boss said this morning just before . . . .” And so on as we fly high above Delaware, or perhaps it’s the Atlantic Ocean, until we land. By then I have advised him how to handle all his problems at work.

The underlying principle in this is that we must make our clothes – a key part of the signal we give the world – work to our advantage at all stages of life. If one is old, we must make old look good, not mock it in our dress or expression. And we must not deny it by dress that would disguise it, or be untrue to it.

This is why I do not wear short pants. I decline to show off my ancient legs. (Actually I never wore short pants.) But I do wear that peaked cap, and I tip it to other older men as I stroll past them, and they usually tip theirs to me. And I have abandoned the devotion to jackets and ties that I considered helpful for professional advancement.

That conviction grew out of an interview I had years ago for a job on a Midwestern newspaper. I came to the interview unjacketed and un-necktied and never got an offer. “You were eminently qualified for that job,” I told myself later. “How come you did not get it?” I decided that my outfit was to blame.

Unfortunately, this insight did not help me get an offer after the next job interview, with the Washington Post, although I came to it wearing a handsome new tie and a well-cut blue blazer. So possibly other issues come into play occasionally.

The blue blazer is still useful for the retiree, and it is generally available. But most of the stores I favor are out of business. Stores and advertising cater only to younger men, and their apparel looks odd on me, or to me, and it doesn’t fit properly, either. Gorsart’s in Lower Manhattan is mourned to this day. It outfitted all of Wall Street for decades, but it didn’t survive the drift toward casual dress that infected even the business world toward the end of the last century. Thank goodness for mail-order catalogues – and Samuel’s Hats.

Shoes are an even harder problem. The calfskin business shoes that Johnston & Murphy sells served me well pre-retirement, but now I wear leisure shoes. They are all uncomfortable, so much so that I ventured one day into a tiny shop on West 30th Street that advertised “custom-made shoes” on a triangular signboard on the sidewalk.

Inside I found a stooped and unshaven proprieter of indeterminate age, pacing about in well-worn slippers and jabbering excitedly in Russian-accented English. I sat patiently on a low stool waiting for him to dispatch two or three complaining customers. Eventually he informed me that he was the city’s finest maker of custom shoes, and that the art was dying. Then he traced my feet in pencil on a sheet of paper and offered to make me “the most comfortable shoes you have ever worn” for a price that staggered me into speechlessness. The leather could be calfskin or doeskin. I chose doeskin.

I gave him a $500 deposit and returned three weeks later for a fitting. I came in just as a portly middle-aged lady was angrily informing him that she would not take the leather purse he had completed for her because the handle was too big. She wanted her advance back immediately, in cash. He claimed he didn’t have the cash. So she gave him her credit card to negate her $200 deposit. He agreed to credit her card for $200, but by this time he was considerably flustered. In attempting to credit her card he managed to debit it instead. “Now look what you made me do!” he exclaimed. She stormed out after that, promising he would hear from her again, or from her lawyer.

“Go! Go!” he cried after her, waving his arms. “She’s crazy! Did you hear that? Goodbye, lady! Do not come back! I am busy.” He turned to me and tried to convince me that reason and justice were on his side. All I wanted was my shoes, so I expressed sympathy and declined to express an opinion. Then he asked me for another $500 advance. “What!” I exclaimed. However, I offered him $100 and we settled for $200.

A week later I picked up the shoes and paid him the balance I owed, an amount that I am ashamed to disclose. I wore the shoes home, and I must say they are more comfortable than any shoes I have ever worn. The style resembles the business shoes I used to wear except that these shoes are a little wider in front. They will not pinch me if I once again lose my balance in the early morning and injure my bare toe (a post-70 danger for male and female alike).

So now I wear a peaked cap, a sport shirt, no tie, khaki pants and the world’s most expensive custom-made shoes. I am one well-dressed dude.