What Would Clooney Do?

In Murdering Ministers, I had Oliver silently sum up a new acquaintance, a mother in her thirties, by guessing she'd never owned a pair of jeans in her life. The judgment was meant to be shorthand for the kind of restricted English upbringing that Joan Quarterboy had been condemned to by her puritan, lower-middle-class parents.

Now my Dad never owned a pair of jeans in his life either. His casual pants were strictly gray flannel, identical to the ones he wore to his factory job. He never owned a polo shirt or a tee-shirt either, his only concession to the elusive English summer being a "sports shirt," a short-sleeved version of the collared dress shirts he wore all year. On Saturdays, maybe a v-neck pullover would replace the weekday sports jacket and tie, always visible at the neckline of his overalls. Sundays meant Church. Church meant a suit.

Me aged 10, Dad aged 49. At home. Ignore bad haircut.

When I was born, Dad was already older than the perennially thirty-ish Joan, frozen by fiction. But he came two generations before her, and my jeans comment is, in his case, a matter of social history. (Dad would have been 98 this year.) When I was a teenager in West London, all the men of his age wore the same uniform. You'd see them in flannels and Marks and Spencer windcheaters, wearing ties to go to the supermarket. "Casual" was a shelf of light-weight clothes that might as well have lived in their suitcases, because they were only sported during those two-week vacations on the South Coast. Of England. The rest of the time, the only casual was business casual. There was no dressing down, only dressing up.

Why bring this up? Well, the prodigiously funny and thoroughly naughty Amy Schumer did a skit in her Comedy Central show a week or so ago about a group of women solemnly visiting the Museum of Boyfriend Wardrobe Atrocities ("Heather dated Mark in his bowling shirt for two years" begins the downbeat audio tour.) It culminates with a display of 5,200 pairs of Crocs. "Did this really happen?" asks a horrified little girl, whose coat stays bright red as the rest of the image fades to black and white.

Here's my problem. The camera scans down one exhibit -- woolly hat, Beats, red striped polo, roomy black khakis, red Converse sneakers. "What you see before you may not look so bad," says the narration, so far confirming my opinion (although the hat is mistake, as hats usually are), "until you know that it was worn by Simon . . . aged fifty-five."

Gasps of horror from the mainly female museum-goers. Gasp of horror from a middle-aged male member of the viewing audience, too. Okay, I mentioned the hat, I use buds,not Beats, and my polos are never crested. But as for the rest . . . (I have a pair of purple Converse, I use them to accessorize a black suit.)

Just add purple Converse . . .

I'm north of fifty-five. All my post-teen life, I've stuck to the narrow pathway of The Gap, never veering into parachute pants or butt-cleavage baring baggies or pastel T-shirts under Armani. My very occasional baseball caps are never worn backwards. I'm a winter. My biggest fashion dilemma in thirty years has been pleated v. flat front.

But it seems even this level of caution is not enough. So now what do I do?

I can't dress like a 20-year-old.

I can't dress the way I did when I was 20.

I can't dress the way my Dad did when he was my age.

What do baby boomers switch to, when their hair also goes winter and their reading glasses stay on all the time?

Where do we go to learn this stuff, Amy?