By investing in a few good pairs of shoes and taking care of them, you’ll be set for years. Every man needs to own a classic black lace-up, a simple style that’s equally appropriate in the office as for dress. Choose shoes that have a slim contour and a rounded (not sharp or square) toe. Decide if you want leather or rubber soles. Leather is essential for real dress shoes, but rubber is great for crappy weather and comfort. Leather lace-ups with heftier soles (military-style ones) are very popular to wear with skinny jeans or trim-cut suits in all sorts of colors. Brown shoes, from light brown to chocolate brown, work with everything, as does a black penny loafer. And of course, Converse low tops in white, gray, navy and black look young and hip, even with slim suits. Leather soled shoes require more attention and require new heel replacements every couple of years. Invest in a good pair of cedar shoe trees (wooden shoe shapers). They keep the shoe’s shape, plus prevent creases, absorb moisture and make them smell better. You’ll also need a black and a neutral wax polish, old rag, and a good brush with horsehair bristles to keep them polished and new.

Mr. B’s Rantz for ALDO – $160

Gucci Tillman Diamante Cap Toe Oxford – $560

Salvatore Ferragamo Caesy Cap-Toe Oxfords – $680

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