There's a feeling that can't simply be written down. Something beyond just things working out, beyond mental health and baseline self-worth. A well-dressed man isn't pretentious—he's elevated, confident. The reward of that investment is captured in one word: timelessness. Fashion never ends—it's a cyclical roller coaster. Surface-level sophistication and quick chic wins dominate the scene, but true style nirvana exists in timelessness.
Look at the last 50 years. The 1980s: My uncle hit the slopes in his neon one-piece, then headed to concerts with his blown-out hair and oversized teal blazer, utterly convinced it would last forever. The 1990s: Flared jeans returned from the 70s as I left the arcade, cranking tunes on my Walkman. They disappeared, only to resurface 30 years later. The 2010s: I left the city for a weekend in the country, wearing those skinny jeans and tapered suits, so proud of showing off my figure. We laugh at these fads now, but they're hard to escape. We've all lost battles against fast fashion—whether from peer pressure, availability, or clever marketing.
Classic military styling has always maintained power through its emphasis on clean lines and practical simplicity. High-waisted trousers alongside fitted, structured jackets create an image of excellence through organization. This approach to tailoring remains timeless despite its sometimes complicated historical associations. Consider the humble 1950s milkman. He showed up for manual labor with dignity, wearing a shirt and tie daily. Working year-round in a subtle soft-shouldered jacket and functional trousers, he performed his duties in comfort while looking remarkably good.
Or think about the iconic Italian American style somewhere between Frank Sinatra and Tony Soprano. The fits were fantastic, especially for larger men. Double-breasted jackets, pocket squares, French cuffs, and gleaming gold watches. These men held themselves to high standards when in the public eye. Men of that era dressed with self-respect regardless of title, career, or background. My father had many jobs—from delivery driver to high-powered salesman. The consistent factor? He was a man who took pride in his appearance.
When I peeked into my father’s closet as a young boy, the past felt tangible. The weight of wool, the depth of tweed, the quiet rhythm of houndstooth. Three staple jackets—each timeless—and what I called the "Anywhere Jacket," the one that worked with everything. Fabrics that held their ground: crisp cotton and sturdy wool. Leather shoes, polished with care, lined up beside a suede jacket reserved for the right occasion. The faint, familiar scent from the top drawer of his pine dresser—cologne, cufflinks, collar stays, watches. A modest collection, built over decades, unchanged by time. If you’ve watched a parent or grandparent grow old, you know this scene. The objects remain, steady and unshaken, as the years press forward.
Whether a watch, suit, or jacket—these tested articles have endured. If they could speak, they'd tell one hell of a story. I've learned that investing in classic pieces isn't just about longevity—it's about feeling damn good now and decades from now. A quality suit built to last will move with you through life's significant moments. It won't split during a wedding dance, won't reveal bare calf during a job interview, and will grow with you through the years (provided you uphold your end of the bargain).
Picture yourself as an old man, dressed for the event—the wedding, the funeral, the christening, the quinceañera—in that suit you took a chance on 20 years ago that still, to this day, works. That's the power of timelessness.
Love you, Dad.
C.L. Brown
