One of the things I’ve learned along the way is that you can look silly—even if you’re well-dressed—when your outfit doesn’t suit the occasion. On the flip side, if you underdress, it quickly becomes obvious that something’s off and that you quite literally don’t fit in.
I once heard Tom Ford say, “Dressing well is a form of good manners,” and I couldn’t agree more. The key is making sure your outfit aligns with the setting, the event, and the people you’ll be around.
Over the past decade, we’ve seen several major style trends come and go—each one eagerly embraced by the masses. First came the “hipster revolution,” where everyone started grooming and dressing a certain way for every occasion. Then there was the “Guy in the Suit” phase—tight, flashy suits worn absolutely everywhere. And now we’re in the “old money” era, where people are channeling the Mediterranean styles of the rich and famous from the 1950s and ’60s.
Honestly, that’s all fine. I enjoy the aesthetic of many of these looks (aside from the overly arrogant suit persona). But here’s the thing: you can’t dress the same way for every occasion. If you ignore the context, you’ll likely look out of place—no matter how sharp the cut, how perfect the fit, or how bespoke the garment.
If you want to be both stylish and appropriate, start by asking yourself: Where am I going? What will I be doing? Am I aiming to blend in or stand out?
Just like you wouldn’t wear a suit to the gym—it’s simply not made for working out—you shouldn’t wear gym shorts to the office. Context matters.
Stay well!