#1 Gentlemen's Hat (for Fall/Winter season)
(This would include hats like a Fedora, Panama style, Cowboy, Beret, newsboy, etc.)
Age: All ages can wear any of these styles
Body Type: Whether you are a big woman, medium woman, or small woman depends on how big you want to go with your hat. A Huge hat on a little woman looks silly, just as a little hat on a big woman does. Try and find the right size to look proportionate to your body. Where your ears sit on your head(high or low) will help you also to pick the best style that works for you. A hat that covers ears that poke out(if that's something you don't like) can help make a nicer look.
Pictures of examples:
The Fashionista might pick a Fedora
Earthy Chic might pick the cowboy hat or suede newsie
The Romantica might pick the blue hat with bow or the red velvet cap
Wild Child might pick the hat with all the embellishments(circle tabs) or the blue castro looking cap that had a turban look to it.
#2 The Sunhat
(anything with a visor or wide brim to keep sun out of eyes)
Age: All ages can keep it neutral or go bright and bold. For the more mature woman, it's nice to have some fancier details, such a shiny hardware.
Body Type: same as in #1, fit to your ears and your body size scale. Big floppy hats are SO fun.
Classy Lady Wild Child
Life Happens, Mariah