A pair of classic dress shoes should be a staple in every guy’s wardrobe. Whether you’re a Wall Streeter or a creative type, the right pair of leather shoes is the perfect cornerstone of your boardroom suit—then jump into the weekend, and they'll make any dark jeans look dressy enough for any fancy dinner you’re committed to.

But don’t make the mistake of assuming, as guys often do, that dress shoes = uncomfortable shoes. These days, even the fanciest kicks are made with guys like you in mind—and in the case of these 15 shoes, that means rubber soles. With heaping amounts of foot-friendly cushioning and a foundation of flexible, durable rubber, these perfect pairs are the best of both worlds: form as well as function.

Here are our favorites from five different categories of dress shoes: derby, cap-toe, loafer, wingtip, and double monkstrap.