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materials. The evolution keeps them in style. In my opinion, Paul Smith can do no wrong with his wingtips.

Tassel Loafers, Penny Loafers or Slip-ons
Be careful! These shoes are like a Cadillac. You can drive a vintage convertible Caddy and look cool, drive an Escalade and look fly, but who drives the other models? Exactly! If you are under forty years of age and do not wear-pleated khaki's, don't do it! You are better off shopping upstairs at Barney's NYC for cooler European versions.

Sperry Topsiders Deck Shoe
Since 1935, these shoes have been a basic on and off the boat. These shoes never go out of style and can look great with any type of style. There are so many brands, especially American brand like Murphy and Nye. An Italian company bought them and really made them stylish and premium. I love the latest classic white and navy deck shoes by G-Star Raw. The last or toe shape is perfect for shorts or jeans.

Timberland Work Boot
Was there ever a boot you could notice five miles away? Whether construction worker, homeboy or Details magazine is my bible man, the Timba boot is a basic. If the yellow is too loud for you just don the brown. Simple and you do not even have to hammer anything. These also double as hiking boots, because they are lighter and slightly more flexible than the traditional Bally. Please don't wear Nike ACG or Merrell, unless you are a poser!

Nike Air Force
These kicks define sport culture. Old school basketball, skate, tennis etc. I think Running shoes are too specific and should never be worn unless you are running. Cross-trainers are too dated and nobody really wears modern basketball kicks. Do they? The Air Force is the definitive "athletic" sneak.

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