At last, we're at the final frontier in accessorizing: the hat. While your grandma probably wore a hat almost every time she left the house, these days they are definitely about making a fashion statement. You can look hippie with a knitted beret, vintage with a cloche, or urban funky with a cabbie hat, just for starters...and they can keep your head warm in winter and shield your scalp from the sun in summer.
The most important thing is to know your face shape and what will work on you. Rounded faces should look for tall, shallow crowns (the kind where it sits high on your head) and brims that are wider than your face. Square faces should look for hats that sit high on the forehead. Long faces should look for deep (sits low on the head), wide and flared brims...stay away from high crowns because they'll just elongate your face further. Heart- and diamond-shaped faces with narrow chins should avoid wide brims; oval faces can pretty much wear anything.
Think balance when choosing a hat. People with more round features should choose more straight lines to balance; if you have strongly angular features, look for swooping brims or curvy embellishments to soften your line.
Body size plays a role also. For the most part, the larger the woman the bigger the hat she can pull off, but I would say not so much for a short and plus size woman (hi!) because a large brimmed hat just makes me look like a mushroom. If you're tall or have a big head, avoid teeny hats.
And about that head size: make sure a hat fits you well. It should be snug, but not tight, across the band. Make sure the hat you choose fits you right without falling around your ears or having to be jammed on and losing its shape.
Are you a hat wearer? What kind?
Going to baseball games
Riding bike rides in the nice weather
Playing outside after work/school
Going for walks outside