There’s an exception to nearly every sartorial rule. A certain well-dressed man can make white bucks look good in midwinter, another looks perfectly natural wearing velvet slippers with a tuxedo. But one rule is hard and fast: Every well-dressed man wears good shoes. In fact, a glance downward is one of the quickest ways to assess a gentleman’s sartorial ambitions. Whether he opts for brogue, wingtip, chukka boot or spectator, he knows that shoes matter.

Here are a few that will make sure you’ll make a lasting impression:

Bergdorf Goodman Rugged Wingtip Brogue

This wingtip brogue is a favorite with jeans or a cords, it’s at home in the city or the country, uptown or down. It’s a versatile without sacrificing style.

Brunello Cucinelli Aged Leather Chukka

Cucinelli’s chukka makes the case that you can and should wear suede year round. Paired with khakis or gray flannel, this is the perfect starting point.

Church’s Cap-Toe Oxford 

Church’s are discreet, well-made shoes. They don’t announce themselves with color, just the reassurance of perfect proportion. Their oxford starts you down the path of a trusted, valued relationship.

John Lobb Classic Double Monk-Strap 

Don’t let buckles frighten you. Iconic shoe-maker John Lobb has a pair of classic double monk-straps. Once you’ve gone lace-free you won’t believe you waited so long.

Tom Ford Zip Boot

Boots have been warn by barristers and bandleaders—they give you authority in any setting. Make sure your trousers are suitably narrow, you’re looking for a lean silhouette. Tom Ford’s version is as good as it gets.   

Red Wing Beckman boot

A more rugged option that manages to avoid making you seem like an urban woodsman is the beckham boot. Made in Minnesota, it’s an American classic, with good reason. Jeans, oxford shirt and a sport coat and you’ve got unimpeachable common sense that impresses.

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