41. LL Bean Wicked Good Mocs
When you're in your Bro cave and have just had your chick tap out like an MMA match, you need something to kick back in. These slippers are warm and cozy. Think: packing a huge lipper, playing NHL, donning these, and kicking her out.
42. Salvatore Ferragamo Wingtip
Ferragamo is the pinnacle wingtip shoe and they're a power-guy staple. Try these "Fano" wingtips that are slip-ons. Slip-ons are key, no bending over. They make a statement but are simple. You don't want to be the lawyer in green crocodile shoes. Remember to take care of these, guys.
43. Cole Haan Penny Loafer
Penny loafers conceived a lot of frat babies in the 1950s. The loafer still reigns supreme. Should it have a penny in it? Absolutely not. You don't exactly need Cole Haan ones, but the brand is still making the best quality out there.
44. TOMS Canvas Classics
TOMS is a great project. For every shoe they sell, they donate a pair to a child in need. They're super chill shoes and support a good cause. At first I didn't like the style, but after getting a pair, I'm hooked.
45. Reebok Question
These kicks were released in 1996, sold out, and set record numbers for Reebok. Iverson wore these shoes during his stellar rookie season. I remember wanting these shoes for Christmas. I still can't figure out what that hexagonal area of air is, but I love the letters on the lace loops.
46. Nike Air Zoom Flight 98
It's been nicknamed "The Glove," because of its ridiculous neoprene zip-up wrap (reminds me of the early Iversons). The shoe was worn by Gary Payton in his Seattle SuperSonic days. It's like having a wetsuit wrap on your foot, but does it do much good? No, but it's so ugly its awesome. Like Snooki.
47. Adidas Samba Classic
Soccer players do not exactly get much attention in America. Mostly because we like a type of "football" that involves bone-crushing hits and dudes who don't fake injuries. That's another story. The Adidas Samba was the hit shoe in my fifth grade, I remember all the kids had them. Instant classic.
48. Clarks Desert Boots
Every brand is jumping on the desert look band wagon (J. Crew makes some solid ones). The Desert Boot defined cool in the pre-hippy '60s. Good on the grown-up weekends of birddogging chicks in Murray Hill. Wait, that isn't grown up at all.
49. Red Wings Irish Setter Boots
Classics. You need a boot like these. They're made to be worn in the field with your 12 gauge and pointer dog. J. Crew makes a great version, but it just doesn't seem right to buy hunting/winter boots at J. Crew, which makes me think of pampered dudes, not hog-packing ultimate Bros.
Totally kidding. If you bought these in order to "tone your glutes," you should consider a self-help group. Or a swift kick to the ballsack. Sure, Joe Montana spackled cheerleaders' faces in his prime, but now he must need Shape-Up money to fund his fourth-string QB son at Notre Dame.