A hat lover from way back, JT has nailed the casual but subtly tailored look, and has a unique take on choosing the right headwear style. Instead of making the hat the main focus of his look, he integrates it with the rest of his apparel. That way, the effect doesn't shout that he spent all day in front of a mirror or simply supporting his local haberdasher. Play around with a few hat styles for fun. If you decide you like the look, there's a big upside. You'll never have another bad hair day -- one that anyone knows about, anyway.