Given the weather and what I'm wearing, I switch between a cowboy, a fedora, a Panama, and a baseball cap regularly. When I'm selling farm / ranch / land proper

Given the weather and what I'm wearing, I switch between a cowboy, a fedora, a Panama, and a baseball cap regularly. When I'm selling farm / ranch / land property, I wear the cowboy with a set of boots. When I'm selling million dollar luxury homes in winter months, I wear the fedora with a wool long coat over a suit. When it's summer I pair the Panama with a linen jacket. My point is, despite some of the negative comments in this thread, it's ok to dress well. In answer to your question, I'd say what you like and what looks good on your body plus the weather / day's activities will guide what to wear. My favorite fedora I bought in Wales, from the same hat company that furnished Churchill's hats. You pair that with a tweed jacket and a wool scarf and you'll be amazed at how you turn heads. I'm not saying I don't love my jeans, t-shirts, and Birkenstocks, but there's a lot to be said for dressing well.