I’ve written it before, I’ve done a podcast on it, and I’ll say it again: a smart wardrobe starts with good shoes. While there are some places where one could cut corners or “cheat” with less expensive shirts, ties, pants, and even suits, shoes are the one area where playing it cheap really doesn’t pay off in the long run.

And when I talk about shoes, I’m talking about real shoes from companies whose heritage, foundation and strength is shoes. This doesn’t include designer labels who grind out a new collection every season. If someone has the money to blow thousands annually on the new and fabulous, super. I’m not interested in that, and I don’t think most pragmatic and discerning men are, either. It’s about shoes that work now, will work next year and will continue to work for the rest of your life. Good shoes can be expensive, but they are worthy investments. This is about the long game. Take good care of them with regular conditioning and shining, heel and sole maintenance and cedar shoe trees between wearings, and they’ll last longer than a good car.

For the cooler months, I have a thing for chukka boots. They’re handsome, masculine, elegant and practical for just about any occasion, depending on the color and finish. Suede is obviously a more casual flavor, while polished leather in a dark shade with a matching (or closely matching) sole can also be worn in dressier suit and tie modes. I have a few pairs, and they’re my steady fall/winter go-to boots with suits or jeans.