 If there was a simple formula for how to dress well and look good, it would go something like this. Step one, choose a jacket that's appropriate for the season. For the colder months, that means flannels, tweeds, and heavier wools. And for the warmer months, cotton, linen, hopsack, and fresco. Step two, layer in a collared shirt. Classic spread collar is going to be more dressed up, a button down collar, more casual and relaxed. Step three, stick to the basics when it comes to trousers. Go with a gray wool or flannel for business or dressier looks, khakis or navy chinos for business casual, and blue jeans for your casual looks. Step four, choose a good looking leather shoe. Dark oxfords for when it's more formal. Light oxfords or derbies for those in-between dress codes. Pebble grain derbies or minimal sneakers for casual outfits. Dressing well and putting together a good outfit isn't difficult. And when you keep things simple, you never look like you're trying too hard.