This very common question can be equated to deeply personal preferences like "What flavor ice cream would I like?"
The cowboy hat is an extension of your personality. Function, form, fit, all are variables that each person has to decide for themselves what fits them best. Here are some basic options to help you decide what type of hat is right for you.
Hat bodies can be made of practically anything, but we'll limit ourselves to the most recognized cowboy hat materials used today. Felt is the traditional choice, made from wool or fur. For the budget conscious consumer a wool hat may be the best thing you can afford. Wool has limitations though; it will absorb moisture quickly, dirt and stains are more difficult to remove, and the shape doesn't typically hold over time. Fur felt is a more durable option. Basic felt hat bodies will be made from rabbit fur, with better bodies having some beaver content mixed in. Beaver fur is more supple, water and stain resistant, so the best hats are pure beaver. A super-fine dress hat will have mostly beaver with some mink or chinchilla thrown in, but also cost the most.
Straw is popular summer choice for many, year-round choice for some. Hand woven from straw fibers and imported to the U.S. where the bodies are shaped and fitted at a hat factory. Straw hats are truly a work of wearable art when you consider how much time goes in to hand weaving each one, then cutting them to fit a specific size, stitching in a sweatband, shaping and finishing the hat. All that work, and they typically last about one good summer season before they crack, break down, or get a large sweat stain. Yes, cleaner is available for a straw hat, but that is often a wasted effort. Think of your straw as disposable when you buy it and you'll feel much better about getting a new one each Spring.
Palm or palm leaf hats are similar to straw fiber but thicker and coarser. I put them into their own body group because palm behaves differently than straw, and also lasts longer than most straws. Palm looks a bit cruder than straw and is much heavier too. One of the best benefits of palm is it's natural ability to absorb water, making it a natural summer hat. Take your palm leaf hat and dip it in the trough (or under the faucet as circumstances allow) and let the wonders of evaporative cooling take place.
Hat color is mostly a personal choice as well. Felt hats can come in a virtual technicolor array of colors, tones and shades.
Black hats are the most common, easy to clean and can look good on nearly everyone. The old adage of "bad guys wear black" went the way of BETA video tapes. If you want to start in a safe place with color you can't miss with a clean black felt cowboy hat.
Dark colors can include mink, chocolate, smoke, navy, midnight, moss, charcoal, putty, pecan, fawn, sorrel and many other names sounding like a fraternity rush class. Dark colors in general hide dirt well, can be used to stand out in the crowd, and are a great way to show you aren't afraid to be your own cowpoke.
Pastel colored hats sound like Easter eggs in the garden but are mostly defined by a single word: silverbelly. Envision these popular pastel color names as a nightclub in Vegas: Sand, chrome, sandalwood, belly, cream, mist, peach, pistachio, pink or blush. These delicious sounding colors are some of the most classic tones available, but the most unique colors are for those daring souls who proudly declare, "I fear no color... your black hat must be trembling in my wake!"
White hats should have no color, no tone, no shade. White hats fall into the wedding dress category; there is white, and everything else. Generally reserved for rodeo queens and superstars of the arena, a white hat tells everyone that you have come to win, and want to look better than anybody else competing.
Brim size is today almost always 4" when you buy a hat off the shelf. But that doesn't mean it is the right size for you. 4 1/4" brims have been very popular with a lot of performance horse riders, the extra 1/4" adding a distinctive flair to a crisp hat shape. Bigger brims are available up to about 5" without too much difficulty (some palms may have a 6 or 7" brim) but you really have to know you can sport a lid that big. A lot of Texas enthusiasts like 5" brims shooting up high, while many Great Basin buckaroos will use a 4 1/2 to 5" brim flat when they work. Vice versa a shorter brim can speak volumes about the bearer. A 3 1/2" brim is used more by the 'Boss' than a ranch hand, and taking 1/4" off a 4" brim can help balance a hat on a shorter man or a small lady. The best advice I can give you with brim cutting (on felt hats only) is to be careful who you take it to. Ask if the hat department regularly trims hat brims, and get a big yes, because "I'll give it a shot..." is not the right answer.
Binding or the ribbon the edge of the brim adds a special touch to a hat. The ribbon can contrast, it can match, heck, it can even be done tight to encourage the brim to 'snap.' But know this: the hat body and the hat binding will often behave differently over time. Most bindings will shrink a bit with exposure to the elements and will warp a brim a bit. I call it character, but you might call it a whoo-hah, bauble or some other term for 'ugly.' It's like your old dog, when it does change you're going to love it anyway. If you hate it, take it out back and shoot it then. Your hat, not the dog.