Ionce caught my reflection in my parent's bathroom mirror: a pair of high-waisted women's jeans sculpted to fit like a second skin, a sharply tailored blazer, a glossy patent clutch nestled confidently beneath my arm, and pointy-toe loafers tapping assertively on the hardwood floor. I laughed out loud—not because the look faltered in execution, but because the boy who had grown up within those very walls would have never dared to wear it. And yet now, with every return to my hometown in Germantown, Maryland, I arrive dressed not simply with style, but with purposeful intention.

In high school, I leaned into a preppy aesthetic—button-downs layered under sweaters, crisp chinos, boat shoes that said just enough but never too much. It was polished, acceptable, and most importantly, safe. I ad

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