The coolest guy out there is the one who knows what's going on and has all the information on fashion but then picks the one thing that works for him. That's all you need—and a brain in your head.
The five things every man should have in his wardrobe are a great pair of jeans, the right-fitting pair of khakis, a bunch of T-shirts, a brilliant watch, and a pair of camping boots.
This may sound sort of silly to most men, but a way to develop personal style is to admire someone you think looks cool who you kind of resemble. No one is going to look like Johnny Depp, so don't go there. But if you need some help, pick someone you dig and watch the way he dresses.
Everyone wants to be comfortable. They want jeans where the waist isn't tight and the legs are loose, but that ideal gets carried too far. I'm not a guy who thinks everybody should wear everything slim, but don't make your clothes so damn comfortable that you're not attractive to people.
When it comes to denim, find jeans that speak to who you are and then throw in a twist. If you're a Wall Street banker, wear low-rise in a classic dark rinse, which will look good with a blazer. If you're a hip-hop guy, wear deconstructed jeans so you don't look like everyone else.
You can take a measured risk in fashion with color. Not crazy color, but you can wear overdyed jeans in khaki or gray and no one is going to look at you sideways. Wearing something other than blue will add character and make you look younger.
There's nothing wrong with getting a manicure and pedicure before you show up at the beach. There's nothing wrong with getting your hair cut even if you want to look like you don't cut your hair. There's no shame in taking care of yourself.
Pursue a passion that takes you past the edge. Mine is ocean race sailing.
There's nothing cooler than American classics, like khakis, T-shirts, oxford shirts, and jean jackets. However, when casual becomes too predictable, it can get schlumpy. When you wear the khakis with the tucked-in pink button-down and the brown belt, you're not saying anything to anyone.
So many men blow it with outerwear. A guy can have his outfit completely together and then he puts on the dumbest coat. It's like women who wear white tennis shoes to work. The jacket is either too old and shabby or it has no character. You only need one great coat.