If I'm able to go, I'll likely be wearing Japan (Hetalia) around the times of any Hetalia events, Madoka Kaname (Madoka Magica) earlier on Friday and/or Saturday, and Momo Kisaragi (Kagerou Project/Mekakucity Actors) on Sunday.
I'm unsure if I'd switch to any others too, but I also have Shiro Isana (K Project) and am planning to have Hotaru Tomoe's school uniform (Sailor Moon), Serena (Pokemon), and Ib put together by then, too, so I also might bring along any of those.
Megacon 2015 [Orlando, FL]
Metrocon 2015 [Tampa, FL] (maybe/likely)
Animate Miami 2015 [Miami, FL]
Shadocon 2015 [Tampa, FL] (maybe/likely)
Holiday Matsuri 2015 [Orlando, FL] (maybe)
Japan [uniform ver.] (Hetalia)
Madoka Kaname [magical girl ver.] (Madoka Magica)
Mami Tomoe [magical girl ver.] (Madoka Magica)
Hotaru Tomoe [school uniform ver.] (Sailor Moon)
Momo Kisaragi [pink hoodie ver.] (Kagerou Project)