My wife and I are in a dressing room at Macy’s. I am wearing a mint green shirt covered with paddleboards.

“You think I can wear this to work?”

“Paddleboards are cool,” Ally says. “And you can wear this untucked with a navy blue T-shirt underneath.”

“How do you know navy blue looks good with green and paddleboards?”

“I just do,” Ally says, bemused that I would even question her color sense.

“I just don’t,” I say, self-consciously aware that each of us knows my aptitude for color matching is just a little better than my aptitude for breathing underwater.


I have taught English for more than 25 years. For all of those years, except this year, I’ve worn a tie. When I first started teaching, all the male teachers wore a dress shirt, a tie and nice khakis. Back in the day, “wears a tie” was a box the principal could check on a teacher evaluation form.

On some days I showed up to work wearing a white shirt with a blue tie and gray slacks. Other days I wore a blue shirt with gray slacks and a red tie. And once in a while I’d wear blue slacks, a white shirt, and a yellow tie. Those last three sentences, by the way, are the most boring sentences I have ever written.

But times have changed and now many men have started wearing clothes to school I might wear on the weekend. Think blue jeans and a casual shirt.

Change is constant, especially what people wear to work or around town. Back-back in the day, both my grandfathers wore fedoras (think Humphrey Bogart) everywhere they went. Then fedoras went out of fashion and people started wearing baseball caps emblazoned with a wide variety of symbols or words. (Think “Nick’s Variety — Eat our Meats!”)


Ally hands me a second shirt to try on. It’s white and covered with small blue compasses. “This is for work?” I say, asking for direction.

“You’ll look sharp,” she says. “Do you know what color T-shirt will look good underneath it?”

This question has all the hallmarks of a challenging riddle. I want to suggest black and yellow stripes, but I know that’ll probably be wrong.

“Light blue or white,” she says, not allowing me time to answer.

“You think so?” I say. The question is clearly rhetorical in nature.

We leave the dressing room burdened by paddleboards, compasses, and lots of plaid, and take my new work wardrobe to the counter. As I watch my mint green paddleboard shirt get placed into a bag, I can’t help but feel wistful.

“No more ties,” I say.

In the tall mirror next to me I catch the reflection of one of my Colonial New England ancestors who could see the writing on the wall and said one day at the haberdashery, as his new Wellington hat was being placed into a box, “No more tricorn hats.”

“You’ll look very nice on your first day of school,” Ally says. “We can lay out your clothes the night before so you won’t have to think about it in the morning.”

“You’re an angel,” I say.


I am standing outside my classroom door and am wearing the mint green shirt awash in paddleboards, untucked so the navy blue underneath can show. Kids and teachers scurry to their Period 1 class. Instead of looking fashionable, I worry I might be mistaken for a McDonald’s Shamrock Shake.

A teacher walks by me.

“Nice shirt!” she says, stopping to admire.

I look back at her in disbelief.

“My wife picked it out,” I confess.

“I figured,” she says.

Gregory Greenleaf lives in Harpswell and teaches high school English. He ascribes, prescribes and subscribes to many old-fashioned ideas, but especially Charles Dickens’ observation that “There is nothing in the world so irresistibly contagious as laughter and good humor.”