10 Dress Shoes That Show Who's Boss

Forget trends. When it comes to exuding power and confidence, the goal is to stay traditional. Peek our editors' picks for timeless shoes that you'll kick up on your corner office desk for years to come.

Black plain toe oxford shoe. photo

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Carmello Oxford by Salvatore Ferragamo

Nothing projects executive-level status quite like a great pair of sumptuous, wholecut shoes, which, unlike oxfords, are crafted from a single piece of leather. The result is a more refined, elegant look than your average pair of derbys. ($995; nordstrom.com)

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Brown oxford shoe with design at the toe and along edges. photo

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Cornwallis Dress Oxford by Allen Edmonds

If the austere absence of detail on a wholecut doesn't appeal to you, consider something with a touch of added decoration, like the understated lace-adjacent broguing on Allen Edmonds's Cornwallis. We're head over heels for it in sumptuous dark chili leather, though it comes in four other colors as well, including more traditional black and dark brown variations. ($395; allenedmonds.com)

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Pair of tan leather dress shoes. photo

3 of 10

Greggo Flat Leather Balmorals by Christian Louboutin

Yes, gents, you too can rock the red sole; this highwater mark of footwear is no longer reserved for your (literally) well-heeled better half. The cobblers at Louboutin have created a robust bench of men's footwear in recent years, but the best—in other words, the shoe that bucks trends and won't go out of style in three seasons flat—bet is the sleek, timeless Greggo flat (shown here in light brown), with its classic cap toe, stitching, and six-hole lacing. ($945; barneys.com)

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Black plain toe dress shoe with lace-up front. photo

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Plain Toe Blucher with Commnado Shell by Alden

Have you ever laid hands on cordovan leather? Touching the stuff feels like petting butter—except you don't walk away with greasy hands. And when you shine cordovan, it takes on an even brighter sheen than traditional leather and retains it for longer. As such, shoes made from it can come across as a little too formal, so be sure to pick up a pair in a more casual blucher cut, like this pair from Alden, to balance that out. ($762; aldenmadison.com)

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Black leather penny loafers. photo

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Turnbridge Penny Loafers by Church's

Every guy needs a pair of loafers in his shoe closet. They're an effortless way to dress up a look; just slip 'em on and you're good to go. Church's loafers are an especially good pick; the company uses a high-quality leather throughout the entire shoe—and few things feel better than slipping your bare foot into cool leather on a hot summer day. ($550; bloomingdales.com).

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Noah oxford shoes with lace-up front. photo

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Noah Oxford by Jack Erwin

If you want to talk "literally never going out of style," look no further than a traditional cap-toe oxford. To add a little flair, spring for a pair with minute broguing around the laces and toe, like Jack Erwin's Noah Oxford. They'll set you apart from the standard oxfords in the room without being as flashy as a pair of wingtips. ($195; jackerwin.com)

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Black dress shoe with buckle strap. photo

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Emmett Monk by To Boot New York

To Boot New York's Emmett Monk is the ideal single-strap monk. Sure, it's a little bit dandy. But that mirror-like luster elevates what would normally be a par-for-the-course monkstrap into a boss-level shoe. Plus, take a gander at that royal purple insole: How's that for majestic? ($395; nordstrom.com)

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Pair of black dress shoes with double buckle straps. photo

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William Monk Shoe by John Lobb

John Lobb's William Monk mixes three subtle, minute details—a tough, grainy pebbled leather; an elegant cap-toe; and a traditional double-strap—for one of the suavest shoes on the market. While all of the parts work together individually, when combined, it's a mishmash of pure and permanent style. ($1,300; barneys.com)

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Dark brown Lace-up cap toe dress shoe. photo

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Austin Brogues by TOM FORD

If you're going to go with a pair of conventional wingtips, go big—like, really big. TOM FORD's Austin brogues are about as big as you can go. From the intricate detailing to the meticulous craftsmanship, they are, in essence, the wingtip perfected. Whether you're walking a red carpet, corporate hallway, or the aisle (congratulations!), these flashy yet classic shoes will ensure all eyes are on you—and whatever you do next. ($1,990; tomford.com)

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Pair of light brown oxford shoes. photo

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Stanley Oxford by Grenson

The sole is the soul of this shoe (and most shoes from Grenson, for that matter). Think of these classics like an inverted Louboutin—the red's on the insole, as opposed to the outsole. Sure, you (and anyone else who peeks your shoe closet) may be the only one who notices. But you'll waltz through the halls of power knowing you're armed with a pair of some of the classiest shoes around. And you know what they say: It's what's inside that really counts. ($325; grenson.com)

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