#3. Kenneth Cole REACTION Men’s Pin Ball Loafer ($40 and up @ Amazon.com)
A double buckle monk strap isn’t for the faint of heart (and in some ways resembles a straitjacket for your foot), but get it right and you’ll up your dress shoe game by 1,000. Originally only worn in the dressiest business situations, monk straps are now worn with everything from formal business suits to jeans and sports coats, reanimated by the male fashion bloggers who love them. The “dub monk” is the perfect marriage of retro and modern for a fashion-forward kind of dude; if your craziest fashion accessory is a loudly-colored tie, keep your distance.
#4. ECCO Men’s Atlanta Wing Tip Oxford ($99 @ Amazon.com)
Also known as brogues, wing tips began early on as Scottish and Irish walking shoes, and for some, still connote an old-world, dumpy feel. But worn with the right combination of self-esteem and style — think dark denim and a blazer — they can add great level of diversity to a wardrobe.
Now, they’re an easy and ubiquitous shoe with a little personality; to guarantee confidence (and pay your respects to the Scottish and Irish dudes who died to give you a pair of badass brogues), throw back an Irish Car Bomb or two before leaving the house.