"When you wear a hat," says Orlando Palacios, of New York's Worth & Worth, "people remember you." Make sure the memory is a fond one. Palacios's approach to hatmaking is personal: He picks the material, brim, and color that fit the head and style of the wearer. If you're getting the ready-made variety, this is exactly how you need to approach it.
First off, start with rabbit. You can get felt hats in vicuna and camel, "but rabbit hair will last 20 years," says Palacios. Only beaver beats it for durability. Like versatile dress shoes, hats that come in subtle shades of navy, gray, and brown go with nearly everything. "If you want to add some color, choose one with a little on the trim," says hat designer Eugenia Kim, "just to dip your toes in." A thin band (the ribbon that rests above the brim) that's around 1 inch wide creates a lean, streamlined look, the same way a slimmer sleeve or tie does. And match the brim to your face. "Whether you have a square jaw or a round face, the brim can accentuate features," says Palacios. A long, thin face will benefit from a shorter 2-inch brim, while a wider face needs a 2.5- to 3-inch brim. If you're a tall guy, don't get a deep crown (the height of the hat from top to bottom). Leave those to the shorter men, and go for something shallow instead.
In terms of placement, set your hat flat. Don't cock it all the way back. "A little snap in the front, just above the eyebrows, is the age-old way of wearing a hat," says Palacios. It's okay to keep it casual: Wearing a fedora with a suit can get too formal, but wearing one with a T-shirt and jacket "dresses up and elevates your outfit," says Palacios.
Finally, remember your manners. Take your hat off when you're at dinner or an event. "There aren't set rules anymore," says Kim, "but you'll know when it's appropriate to take off the hat."