i'm overweight about 300 lbs, 6'1 im trying to decide on a hat to just wear whenever. got it between 3 types: Newsboy Example: Christys' Wool Newsboy Cap - The Claudius at MensHats.com Fedora/Trilby Example: http://images.freshnessmag.com/wp-content/uploads//2010/08/Leather-Band-Fedora-570x665.jpg Urban Cap Example Site Disclaimer
http://www.blue-tomato.com/medias/generated/generated_m1ufIor0AWzb8RTHiWF968-30_600_600.jpeg different urban cap.
Hats like most accesories depends on the season/weather for spring/summer i'd go with the fedora because it is naturally associated more with summer and can be worn with shorts to the beach, around town etc, yet like the one you posted can be worn more formally as well. For autumn/winter i like the newsboy cap, it pairs better with heavier clothing and layering etc and really comes together when worn in conjunction with a scarf. The newsboy can work in summer but tends to create the preppy-type look, which i really like but depends on your style. But go with what you're more comfortable with, fashion is most effective when it's a personal choice and reflects your own personality.
Look at my profile. GET A CHULLO! They're warm and comfy especially for the winter season...but also they're just so damn adorable! But if you just want one of those 3...I'd go for the urban myself.
You can't go wrong with the Bear Bryant look College Superfans -- Week 10 - Photos - SI Vault Roll Tide.