Learning to Wear Confidence
How I went from indifference to identity, and why it changed more than just my closet
The Early Years: Function Over Form
There’s a photo of me from college that I keep tucked away in a drawer. I’m wearing long, baggy cargo shorts and a graphic t-shirt—something free from a campus event. My posture is slouched, my expression neutral. I’m smiling, but everything about the outfit looks like it’s trying not to care. That was me. Functional. Presentable. Invisible.
For most of my early life, clothing was a problem to be solved, not a joy to be pursued. I didn’t grow up caring about fashion. I didn’t have stylish older siblings or a grandfather in bespoke blazers. I was middle-class Southern and practical to a fault. Clothes were things you bought when the ones you had wore out. That was it.
The Rebellion Against Fashion
What’s more, I didn’t trust fashion. I had a strong streak of cultural contrarianism—skeptical of consumerism, wary of appearances, and instinctively resistant to anything that smacked of received wisdom. In my mind, people who cared too much about clothes were either insecure or shallow. I prided myself on being neither.
But the irony was—I always noticed what other people wore. I noticed when someone looked like they belonged in their clothes, when they moved through a room with a kind of quiet dignity. I just didn’t think that kind of presence was available to me. Or worse, I thought pursuing it would make me a fraud.
The Wake-Up Call: Square-Toe Shoes
In my 20s and early 30s, I was building a career and a family, and fashion remained low on the priority list. If I was presenting in front of a client or attending a formal event, I had a few off-the-rack dress shirts and a single suit I wore to everything. I told myself it didn’t matter. That depth was more important than polish. That the world didn’t need more shallow men in sharp suits.
Then came the square-toe shoes.
For years, they had been my go-to dress shoes. Black, plasticky, and hard on the feet—but cheap. I wore them to weddings, client meetings, formal dinners, and never thought twice. One day, while browsing online, I stumbled on a thread about men’s style. It was filled with photos, commentary, and advice—most of it opinionated, some of it downright smug. But there it was, in bold letters: “The square-toe dress shoe is the ultimate fashion sin.”
I froze. Wait, what?
That was the first time I realized: I’d been doing it wrong. Not just in terms of trend, but in terms of care. I hadn’t paid attention. I hadn’t taken myself seriously enough to ask, “Is this really the best I can do?” It was a small moment, but a profound one.
Discovering Confidence Through Fit
Soon after, I bought a pair of Allen Edmonds. Not flashy, just simple and well made. The first time I wore them, something clicked. I didn’t feel dressed up. I felt grounded. I wasn’t trying to impress anyone. I just felt more like myself. That was new. The soft leather creaked when I walked, the solid soles clicked confidently on the floor. For the first time, I understood that sound could feel like self-assurance.
From there, the journey accelerated. I started paying attention to fit. I learned what made a shirt drape correctly, why some jackets looked boxy and others elegant. I discovered tailoring—and what a difference a few stitches could make. I experimented. I made mistakes. I bought things that looked great on the hanger and awful on me. I learned.
The Compliment That Changed Everything
There were key moments: finding a tailor who didn’t just alter but educated. Receiving a compliment from a stranger—an older woman who approached me and said, with a knowing smile, “Young man, that is a wonderful outfit.” I was wearing a casual Neapolitan suit, open-collar shirt, and a pocket square. It wasn’t loud or flashy. It just worked. And for the first time, I felt like I was wearing something that reflected me—not a version of me, but me.
It wasn’t just about aesthetics. It was about confidence. About presence. About knowing that when I walked into a room, I didn’t have to think about my clothes—I could focus on the conversation, the relationship, the work. Because something inside me had settled. I had found a kind of harmony between the inner and outer life.
The Art of Effortless Grace
The Italians have a word for this: sprezzatura. It means effortless grace—the art of making what is careful feel natural. That’s what I’d stumbled into without knowing. I wasn’t trying to look perfect anymore; I was trying to feel at ease. Over time, that became my definition of style—not polish for its own sake, but ease born of confidence and authenticity.
From Learning to Legacy
Over time, I realized something deeper: I wasn’t just learning how to dress. I was learning who I was becoming. My style started to reflect not only my preferences, but my convictions. I didn’t want flash. I wanted elegance. I didn’t want trend. I wanted timelessness. I wanted clothing that could last through seasons—of weather, and of life.
Lately, my taste has continued to evolve. I find myself drawn toward a more British sensibility when it comes to formal suits—structured shoulders, deep lapels, understated tones. But for casual suits and sport coats, I still love the easy drape and relaxed feel of Southern Italian tailoring. I’ve even begun adding English tweed jackets to my fall and winter rotation, and recently started investing in beautiful scarves to round out certain looks. These small touches matter to me now. They feel like punctuation in a sentence I’m still writing.
Eventually, this quiet personal journey led to something bigger. A business. Patrick O’Shea, a friend whose style I had long admired, founded SPO 33—a made-to-measure menswear venture rooted in the very values that shaped our shared journey: intentionality, confidence, relationship, and care. I joined as his business partner. We don’t sell image. We offer presence. We help people discover what it feels like to be fully themselves, down to the last detail.
The Quiet Confidence of Care
And still, I’m struck by how many men today don’t think what they wear matters. Some even believe it’s not masculine to care about clothes—as if paying attention to beauty and fit were signs of weakness. I think that’s wrong. I think dressing well is one of the quietest, most consistent ways a man can say: I am here. I am ready. I respect myself and those around me.
If I had to describe my current style in three words, I’d say: Timeless. Elegant. Empowering.
I still think about that old photo sometimes. That version of me wasn’t false—he was just early in the process. He didn’t know, yet, what good clothes could do. Not just for posture and perception, but for soul. He didn’t know that style, when done right, doesn’t cover you up. It draws you out.
Style, when done right, doesn’t cover you up. It draws you out.
Question for you: Which habit is holding your wardrobe back: not knowing, not noticing, or not bothering?
If this story nudged you to take a next step, Patrick O’Shea (founder of SPO 33) offers a short, no-pressure consultation to talk fit, fabric, or where to begin. Book here: SPO 33. Or reply to this post and I’ll connect you.