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Those penny loafers in the back of my closet are plenty old, but the wise and weary eyes gazing out from their penny keepers are even older.

Many years ago – before the house, the family, the endless yard work – a girlfriend did a jaunty, cheeky thing. One night when we were out on the town, she plucked the two pennies I’d already stuck in my shoes and replaced them with dollar bills, folding each one over and over until only George Washington’s upper face showed on each tiny square before carefully squeezing them into each little slot.

Those twin Georges have been there ever since, and they’ve always gotten a laugh from folks who happen to notice. And even though
I haven’t worn those happy loafers in ages – they turned out to be half a size too tight – I’ve kept them for a specific, fatherly purpose.

One day, I thought, down through the years, I will pass them on to my son.

And my sentimental (and thrifty) plan would have worked perfectly if it hadn’t been for one slight twist that even the worldly, wizened father of our country might not have anticipated.

Somehow, somewhere, when I wasn’t watching, cute little Will grew up and became the lanky, loping figure I barely recognize going up and down the stairs. And the most galling thing of all? He is now wearing shoes two sizes bigger than mine.

Sure, I get that boys get bigger, and fast. But Will is only seventeen, and just about to enter his senior year of high school. Exactly where was I on the highway of life when he zoomed past at a speed sure to draw the attention of the authorities? He matured out of nowhere, it seems, and he delights in rubbing it in by constantly challenging me to stand back-to-back to measure our respective heights. (I maintain I’m still taller, but mother and daughter, squinting in judgment at the top of each head, have lately ruled in favor of the boy.)

And his feet? They’re boats. Big enough to waterski on without the assistance of actual water skis. Already maxing out the perimeter of his size XL beach sandals. Long enough to “hang ten” completely on their own. 

Even though I was a painfully late bloomer, I did eventually fill out and sprout up as the years went by. But this guy is already morphing into some kind of long-armed, furry-legged, wide-shouldered, teenage Bigfoot, and there appears to be no end in sight to the growth spurt (and let’s not get into the dimensions and proportions of that head of floppy, gnarly hair).

Opening my closet door, I just stare blankly at the footwear I’ve kept for so long and always had a mind to bequeath. Besides the penny loafers, I have a nice pair of lace-up dress shoes with gently narrowing toe boxes and extra-cushioned soles. There’s a pair of chocolate-brown slip-ons that aren’t too beat up. I even have a pair of brand-new athletic shoes still in the box I never got around to wearing. Everything could have been his. All are now too small.

But the truth is, even though these shoes are lightly used, Will has noted that my carefully preserved collection – like so much other clothing and accessories I’d looked forward to passing along – has fallen slightly behind the times. And as his sense of style matures, he has informed me that certain items necessary to a civilized man’s existence, such as shoes, ties, belts, watches, and sunglasses, ideally should have been purchased in the current century.

I have to admit that when Will was a little guy, I did my best to skirt high prices when it came to the endless stream of shoes he needed and tried to bamboozle him into choosing appealing, yet sensibly priced cleats, cross-trainers, and sneakers. But he wised up as he got older, and soon enough I found myself at the cash register with no hope of escape, my only consolation the tattered coupon that got me a mere 10 percent off the high tops he needed.

Will’s mom said not to protest, that athletic shoes are a special part of every boy’s identity and we shouldn’t balk at a few extra dollars here and there. And at the rate he’s growing, he barely has time to give casual shoes full life on the pavement before they need to be replaced. 

But when it comes to dressing up, I do have to admit: The kid has good taste, and he knows the look he’s going after. And even if it takes an eternity for his clothes to find their way to the hamper, Will is fast becoming a guy who takes care of his stuff. A single sport jacket, a few dress shirts, and a clutch of ties hang neatly in his closet. There is even a multi-tiered metal shoe rack in the back for his shoes, boots, and slippers. And though most of his boyhood toys have migrated to the attic, select mementos – the lava lamp he won at an arcade and the Darth Vader tube that once held a pair of Star Wars pajamas – are carefully arranged on his dresser alongside his first bottle of men’s cologne. 

As for me, I continue to curate my late-20th-century old-dad look by wearing tennis shoes with pleated khakis and insisting that the bathing suit I’ve owned since 1998 is still fashion-forward. But I don’t mind being stuck in the past. It only serves to remind me that Will, like Washington who started out in varying fits and starts before eventually finding his way, isn’t just growing up. He’s becoming his own man. 

And what to do with all these old shoes? Take ‘em all if you like – the loafers featuring our wise and watchful first president included. Like me, they might be a bit fusty, scuffed and out of date. But look on the bright side. Wherever you go, you’ll always know you have two bucks. 

Tony Farrell has written about parenting for many books, magazines, and websites. The father of two, Tony has written the DadZone since 2009.
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