1. Captoe – Conservative but elegant even in a casual format. Finally – what every man might secretly desire. Because what well-dressed man doesn’t love shoes? Blacksuede cap toe from Mark McNairy, $398.00
2. Monk Strap One step beyond the one thick strap you usually find on a monk-strap loafer, this modern version has two thin straps with a lighter buckles.
Choose this in the morning when you feel like making an understated, stylish statement. Leather shoes ($1,260) by A. Testoni.
3. Wing tip – Most high-powered execs have got a need for them Not all wing tips look right with suits. But this pair, with its closed-lace construction, slim leather soles, and rich brown patina, could hold its own with most any two OR three-piece suit.
Leather shoes ($595) by Fratelli Rossetti.
4. Oxford Lace-up – Casual dress down days for sport coats with slacks You can’t get much more elegant than a finely made black lace-up, particularly when the toe looks like this: not too pointy, not too round, and not remotely square.
5. Loafer – Say no to laces. Face it; some days just call for no ties. A hand-rubbed, skillfully shaped pair of do-I know-what-to-wear-or-what loafers like these Berlutis are just the kind of shoes that command respect. Even at the office. Leather loafer ($760) by Berluti.
6. the Derby – For Every Day: The Shoe You Can Wear Anywhere. In dreams there’s one pair of shoes you can wear everywhere, all the time, from tuxedos to track pants. We’ve looked, and honestly, dreams are just that. What we have found though, is one pair of shoes that you can wear almost everywhere: these chestnut-brown derbies from the undisputed champion of Swiss footwear, Bally. Leather Scribe derbies ($725) by Bally
Color Rules: You need 3 different color shoes- dark brown, black and cordovan. Want to focus on one? Dark brown owes its versatility to a few key features: their rich color (a dark brown beats black for versatility any day), their knack for blending well and being less obvious than black, and their range in hue which reaches farther and wider than pretty much anything else around. Consider them the skeleton key to your closet and wear them with care. Because most other colors aren’t nearly as versatile. Relax on the weekend and on a casual evening with a light shade of brown and for an elegant night, or an important meeting, a dark chocolate-ly shade.