1. Find a color that complements your skin. Hats are closer to your face than anything else you wear. Hence, if the color isn't flattering, it will be especially noticeable. I know it's the sweetest hat you've ever seen, and it would look so great with your boots, and it matches your eyes, and so on. Try the hat in a natural light. If it makes you look sallow, put it back.

2. Wear your hair differently. Many women just plunk a hat on top of their everyday hairstyle. If you already have a wide face, this can exaggerate it to an unflattering effect, especially if you have long or full hair. If you really like a particular hat, but just don't think it works on you, try pulling your hair back in a tight chignon or a low ponytail at the nape of your neck, or pinning the front sections back. At the very least, tuck hair behind your ears. It may improve matters dramatically.

3. Choose a hat that works with your face shape. If you have an oval or triangular face, you're one lucky bird. You can wear almost any hat, and you can wear it as far forward or back as you please. You can also pick any kind of brim without looking like you're wearing a life preserver on your head. The hat's crown (the part that fits down over your head) shouldn't be narrower than your cheekbones.

If you have a round or square face, wear your brims on an angle when possible. You'll want the crown of the hat to be at least as wide as your face. Hats with a wide, high crown will work especially well. You might also consider wearing earrings to add interest.
If you have an oblong face, stay away from tall hats. Wide brims will counterbalance the vertical stretch. You might also try pulling the brim down to your eyebrows to shorten your face and to hide excess forehead.

4. Make sure the hat is angled to its best advantage. If a hat doesn't look good when you first try it on, you may not be wearing it far enough forward or back. Many hats, especially stiffer hats made of felt or straw, will also wear better when you tilt them slightly. Try angling your hat to the right or left, and look at it from every direction in the mirror. It may look good from the front, but terrible from the side. Keep fussing until you find a position that works. If you can't, assume that the hat is ugly and keep shopping.

5. Be sure you're wearing the correct size. The average female head size is twenty-two and one half inches. If the hat comes down over your ears, or falls off easily, you'll want a smaller size. If you fuss with your hat, or if it makes your forehead itch, go up a size or two.