Oxfords are your starting point. They’re found in a few flavors: plain toe, apron toe, and cap toe. Consider owning at least two pairs - one black and one brown - for versatility across your wardrobe. Black oxfords can pull double-duty, with a muted shine for semi-formal wear, or a high-gloss shine for those black tie affairs. Your browns will look great with dark jeans or with a dark grey or navy suit.
Leave your pennies in your pockets, but wear loafers nonetheless. In addition to skipping the coinage, it’s probably best to shy away from loafers with tassels, though new styles have seen resurgence in recent years. The sharpest loafer is the one that is neither too pointy nor too round, and that has a solid build that avoids looking at all like a moccasin.
Wingtips are easily identified by the ornate holes (called “brogues”) that line the shoes’ uppers. Wingtips were once suited for serious occasions, but rocking them with jeans is the new thing. Wingtips can be found in black or brown, but if you are going to have just one pair, we vote brown - they can dress up or down with jeans or a jacket.
Monks are back, and they have a score to settle. After years of being shunned in sartorial circles, the monk has reclaimed its place at the top of a well-balanced shoe arsenal. Monks can be found with single- or double buckle closures. Either look is fine, but we’re fans of the double-sided variety
Driving shoes are exceedingly comfortable, and are right at home behind the wheel. These slip-on shoes are ideal for pairing with chinos or jeans – not dress slacks. That being said, every guy should own a pair of nice, leather drivers for those quick beer trips.
Boots are capable of substituting, or adding to, any of the above shoe styles. Considering the plethora of boot options that mirror most of the shoe styles above, as well as unique styles like Chukkas, every guy should own at least one pair. The best kind is one with that hard-to-find blend of class and ruggedness.