Silver-plated plaque belt, $49.50 at J.Crew
Here's the good news: you can be a very well dressed man with a belt collection that you can count on one hand. You don't need a lot. You need timeless styles that can work with a range of pants and look good while doing it. The slide belt with an engine turned silver buckle is a classic that you can wear for the next few decades at least. About an inch wide, they're neither too slim and fancy nor too wide and casual. Which makes the belts ideal to sport with everything from jeans and chinos, to navy suits and flannel trousers. J.Crew sells a silver-plated starter version, but purists demand a sterling buckle and a bridle leather or crocodile belt strap. Those will cost you, but when you start to calculate cost-per-wear, you'd be surprised at the value. Whether or not to monogram, of course, is up to you.