"You'll grow into it." — A Personal History

A red baseball cap is the first thing I remember about clothes.

It said "Little Slugger" (Sluggard?), it had elastic on the back, and it was the best. When I lost it in Jo-Ann Fabrics while my mom was shopping for costume patterns, I cried. I probably even untucked my shirt in red-eyed frustration. That, of course, would have been a major infraction in the Putnam household. If we were "going in to town," my shirt tails better have been secured.

So, this was me as a little kid in the early 1990s: Collared, short-sleeve shirt held hostage by my waistline, navy or khaki slacks, and classic blue Keds.

Pretty standard if you're homeschooled.

On the farm in the rolling hills of southwest Missouri, it was a different story. I had some autonomy, most of which was exercised on Big Smith overalls, double-layered flannel shirts, and oversized, knee-high mud boots.

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THE EARLY YEARS

No, your eyes are not deceiving you. There are two flannel shirts in this picture. Yes, one has cut-off sleeves.

As the youngest of four kids, hand-me-downs dictated the contents of my dresser drawers. We thrifted often—Goodwill on 32nd Street in Joplin was mom's favorite designer store. "You can find Dockers," she'd say. "Banana Republic's there, if you look hard." Yes, Mom, the cream of the crop.

The number of times overalls appear in these pictures is proportional to the percentage of my wardrobe they occupied in the early years. I wish I could say that I never wore overalls in to town. I wish I could say that I didn't wear overalls almost every day in sixth and seventh grades. I wish I could lie.

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HIGH SCHOOL

Right around high school, things took a turn for the confusing. As the grudging victim of a dress code, my wardrobe was converted to trousers and collared shirts. I lusted for full-price jeans from the coolest store in Northpark Mall: American Eagle. Every once in a while, we'd splurge.

Proof that I was a master of this picture-pose long before I'd ever even heard of Oak Park High School. Not sure what's going on here: Cargo pants, polo, camo, misshaped cowboy hat? And I'm pretty sure that's a "Vote for Pedro" ringer T-shirt underneath. I wish I could confidently say this was a spirit day at school, but it's not far enough outside the realm of possibility for normal 11th-grade attire. Except the hats, obviously. Those weren't allowed. And that lunch box was one of the sweetest things ever.

Fairly standard, ill-fitting suit option for a school formal. At least I wasn't wearing a pastel tuxedo like the other guys.

But mostly, my closet was stocked with the cast-offs from my brother's school attire from nine years earlier. (Remember what I said about hand-me-downs?) Threadbare Arrow shirts, khakis with a 32-inch waist.

White collar. Blue undershirt. Lookin' good.

Mom and Dad's explanation? "You'll grow into them, son." Made sense at the time. Buying a size larger was hardwired into my purchasing decisions. But the joke was on me; I stopped growing right around the time I turned 15.

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COLLEGE

One time, at JBU: Free at last from high school dress codes, my freshman year was mostly characterized by trucker hats, T-shirts, light-wash jeans, flip-flops, and Jack Johnson.

College was the first time I ever wore sweatpants to class. I fell asleep. I began to wonder if what you wear actually does affect your performance. Back in high school, that was the administration's reason for the seemingly oppressive dress code, but I never believed them. Until I started wearing a tie on exam days.

Then I noticed the way my 40-year-old brother dressed for work. Shirt, tie, pants that weren't too big. His care with his appearance showed his care for his work and his family of four. I noticed kids whose pants were closer to their knees than their waists. I noticed that a man dresses differently than a boy. And I noticed a difference when I tried it on for size. I was more alert, more put together, more effective. The mental pumps were primed.

When it comes to what you wear, you're presenting yourself. Sure, it's an opportunity showcase your individuality. But more importantly, it's a chance to say "Here I am. Expect this."

Style? It's an extension of reputation. You grow into it.