Oxfords

If you're only going to have one pair of dress shoes, an oxford should be your first choice. It's a look that can match with your most formal alternatives, so you'll never be out of options for a large work event—or if you have to wear a tux. That's thanks to the oxford's "closed-throat" construction, in which the leather around the laces (the quarters) meets at the base, where it's sewn into the vamp, the leather that stretches down your instep and towards the toe.

To be honest, you don't need to spend much effort on the terminology. Examine the top of the shoe, near the eyelets. Does it resemble a "V" rather than a series of parallel lines? You're wearing an oxford, and the sleek silhouette ensures that you'll seem appropriately put-together for any dressed-up occasion.

Derbies

Derbies are technically less formal than oxfords, but don't let that deter you. A decent pair can go with almost any suit (though perhaps not a tux if you'll be surrounded by black-tie traditionalists). Furthermore, the open-throat silhouette—the leather surrounding the laces goes parallel and over the vamp—can be worn with everything from denim to tweed trousers.

Brogues

When we talk about brogues, we're not talking about the silhouette itself, but rather the embellishment that goes on top of it. The characteristic perforations were originally used to drain water from the shoes worn to trek over Irish bogs. It's now purely decorative, yet it's still a staple of modern dress shoes.

You might also know brogues as wingtips, and there's a good reason for that. Two of the main styles you'll find have decorative "wings" fanning out from the toe of the shoe. With longwings, they wrap all the way around to the back of the shoe. They wrap to around mid-foot with shortwings. Brogueing can also be found on cap-toes and other design components. Those elements could be found on a pair of derbies, oxfords, monkstraps, or even ankle boots. It's all about personal preference when it comes to brogues.

Loafers

Some people used to think loafers were too casual to wear with a suit. Simply ask your father—or perhaps your grandfather. Fortunately, those days are long gone. Slip-on shoes are now available in styles that are elegant and attractive enough to go with even the sharpest two-button suit. The most common variations are penny loafers and bit loafers. On pennies, there's a strap across the shoe with a cutout that, according to loafer lore, was designed to hold a penny (it probably wasn't, though it's still a fun story). Bit loafers feature a metal piece across the foot that's purely for show, but still looks cool.

Chukkas

Chukkas are a bit of a gamble. Some are clearly not intended for formal occasions, and would look more at home on a building site than in a boardroom. Others, on the other hand? They're just as sophisticated as the other styles on this list. The key is to concentrate on a streamlined silhouette and raised construction. Generally, that means the shorter-than-average boots will have a narrower toe and clean lines leading up to an ankle that'll sit nicely under a pair of suit trousers. Look for that, plus a not-too-chunky sole, and you'll be in good shape.

Prop styling by Miako Katoh; Photography by Allie Holloway