I am, by a matter of months, a member of Generation X, clinging to the back bumper of it, but a member all the same. I grew up chasing a soccer ball across patchy fields and feeding cassette tapes into a Walkman until they wore thin. Mine was the era of the slacker, the alterna-teen, the flannel-wearing prophet of grunge who had decided, on principle, that trying too hard was the one unforgivable sin.
We dressed to disappear into one another. Jeans and a t-shirt. The t-shirt could advertise a band, a soda, or nothing at all, and it didn’t matter, because the whole point was that nothing mattered. Effort was suspicious. Polish was for people who had something to prove, and we had decided, with the lazy confidence of the young, that we had nothing to prove to anybody.
I carried that creed into my late twenties the way you carry a smell you no longer notice. It nearly cost me my marriage before there was a marriage to lose.
A Gasp at the Door
I met Catherine on a Catholic singles site, back when admitting you’d met someone online still required a small swallow of pride. We wrote letters—real, searching, months-long letters—before I ever booked the flight to meet her in person. Our first visit was casual and easy. But the next evening we had reservations at a nice restaurant, and I arrived at her house dressed for the occasion as I understood it: jeans, a t-shirt, sneakers, and white tube socks.
She stepped out of her room in a lovely dress, radiant, clearly having understood “nice restaurant” in a way I had not. She took one look at me and gasped. Then she said she’d be right back, retreated to her room, and changed into something far more casual to match her hapless date.
What I didn’t know until later is what happened behind that door. She told her mother she wanted to end it that very night and send me home. And her mother, to whom I owe a debt I can never repay, said something I’ve carried ever since: “Clothes can be changed. The man inside is what matters.”
So Catherine gave me a chance. The chemistry that sparked that night had nothing to do with my socks and everything to do with the man her mother had told her to look for. We were engaged not long after, and married not long after that.
The Slow Renovation
Marriage came with a quiet, merciful demolition project. One by one, Catherine retired my old t-shirts—garments that, if they had ever been in fashion, had fallen out of it a decade or more before. I didn’t fight her. In their place came button-up shirts, khakis, jeans that didn’t look like they’d been issued at a skate park, loafers, actual shoes that were not running shoes pretending to be footwear.
And there I more or less stayed for twenty years. The trouble was that I remained a passenger in my own wardrobe. Catherine bought my clothes for the whole of our marriage, but a husband who won’t come to the fitting is a hard man to dress. Things fit roughly. I looked better than the tube-sock years, a low bar cleared, but I never looked good. Vaguely preppy, vaguely casual, perpetually a size off.
Meanwhile, my wife was becoming an authority on exactly the thing I kept ignoring. She wrote a book, A Return to Beauty, about dressing in a way that honored Catholic tradition without surrendering an ounce of loveliness. One idea in it lodged in me and would not leave: the threefold shape of modesty. Dress with sufficient fabric. Dress for the occasion. And dress for one’s state in life.
That last one is the sneaky one. A duke who dressed like a vagrant would be a kind of insult to his office. So would a CEO who came to the boardroom got up like a rebellious goth teenager. The clothes are supposed to say something true about where God has placed you.
I am no duke, no lawyer, no doctor. But somewhere in those twenty years I had become the board chairman of a Chesterton Academy school and a member of my parish’s building committee. And I was still dressing like someone who put the minimum of effort into his wardrobe.
Biting the Bullet at Forty-Eight
So this week, at forty-eight, I finally did it. I asked a friend, a Catholic man with genuine style, where a clueless person might shop in our small city. He gave me the name of a store. I went, with Catherine at my side, and I told the people there the plain truth: “After forty-eight years, I’m ready to dress the way I should. I have no idea how. Help me.”
They went to work. My wife advised. I tried on more clothes in an afternoon than I had in a decade. Things fit, and then the tailors made them fit better still. I walked out with a few basic, well-made outfits. It cost more than I’d spent on clothes in the previous eight years combined. And it was time.
Two Things My Wife and My Father Taught Me
Two realizations have been working on me since.
The first came courtesy of my elderly father, who showed up one day in a threadbare t-shirt I recognized from my own childhood. “Dad, is that shirt forty years old?” He laughed and confirmed that it was. That’s frugality at a level I can only admire, and it’s the water I swam in growing up. I absorbed by osmosis the idea that spending money on how you look is a vanity, maybe even a waste. There’s something good buried in that thrift. But I’d let it harden into an excuse.
The second realization came from Catherine herself, and it stung in the way only true things sting. “When I met you,” she told me, “I thought you were a loser by how you dressed.” Then she got to know the man her mother had banked on, the one who’d graduated near the top of his class and played all-star ball. “You were hiding your real quality,” she said, “behind a costume of not caring.”
For years I’d told myself the opposite was the virtue: don’t judge a book by its cover, let people discover the good stuff underneath. But Catherine turned that around on me. The cover is not supposed to fool anyone. The exterior should reflect the interior, not disguise it. To dress beneath yourself isn’t humility; it’s a small dishonesty, a way of making the world work to find out who you are.
The man inside is still what matters most. Catherine’s mother was right about that, and her mercy is the reason I have a marriage at all. But twenty years on, I’ve finally understood the other half of it. The man inside deserves a shirt that tells the truth about him. And at forty-eight, with a few well-tailored outfits hanging in my closet, I’m at last dressed like the man I already was.