Hi Ain't No Mom Jeans --
Ali - Thanks for writing in! Baseball hats are so crazy-relevant right now that I say, keep wearing 'em! Seriously! Want some inspiration? Try this...
Personally, I'm kinda loving the look of keeping your hair down with the cap (like that cutie in the glasses), or in a low, messy pony (like the J.Crew image above). I'll bet a romantic half-up/half-down do' would work also.
Here's my take:
(wearing: Levi's denim leggings, Frye Carmen 3 strap boots, J.Crew factory chambray shirt, J.Crew sweatshirt, Anthropologie poncho)
See that "C"? It's for the Coopertown Padres, Mamas.