Leather dress shoes are tricky. For any guy who wears them on a daily basis for work or otherwise, it makes sense to invest in a high-quality pair. But for those of us who only break them out for weddings and other important situations, a $500-plus pair feels like throwing too much money at a problem that doesn’t exist. In the past, this left most men a last resort: the bargain bin full of plasticky leather, square toes, and boat-sized soles. Fortunately for everyone, those days are gone. Smart shoemakers have found new ways to offer a great craftsmanship on a relative budget. We looked high and the low to find the perfect pair of dress shoes — whether you’ll be wearing them five days a week or five days a year. These are some of our favorites.