Look #2: Vintage
When I first put this look together I didn't expect it to look so vintage. I just liked the combination of blues and polka dots. Looking at these pictures now, it kind of reminds me of "A League of Their Own".
If you prefer a more retro look, pair your hat with classic, lightweight fabrics like chambray, searsucker, or other cottons textiles. Denim works, too.
Again, you can go in a tom-boy direction, but add "girly" details which contrast nicely with the more androgynous pieces. Polka dots are perfect, or simply add pearls and pointed flats. Here's a good example featuring a 50s style a-line skirt. Love her style!
If you're not sure if a hat will flatter you, try a couple in colors that flatter either your skin tone or your eyes. The blue of my hat matches my eyes and is what eventually convinced me to buy it.
This is my favorite photo from the test shots I took indoors. It is currently my profile picture on Facebook. My dog looks unamused, as usual.
Thrifted hat - Thrifted chambray romper - H&M cardigan - Aldo bag - crappy black flats