The last time I saw Mr Two Bits was at the 2008 South Carolina game. He of course retired the next week. I've been a Gator fan since 1982 when my dad took me to my first game at the Swamp (vs. Miss St.). Growing up in Florida I had to make a choice. That day at 10 years old. I became a Gator. Mr Two Bits led a cheer 5 feet from me. He has been a part of many Saturdays for me since.
I went with a very simple silhouette with the trademark tie visible.
One word of warning. Make sure your selection is original. If someone traces a photo and silhouettes it, it would be a copyright infringement and there is software that can track it, and you wont be able to use it. Make sure it is original artwork.
This is an original drawing that I did. Not a photo...
Good luck, there are a lot of talented designers here. One of us will be able to nail this thing for you.
#2 looks good for that version. Can you make it w/ the colors I suggested? I wasn't sure if the orange sign would look better w/o the words (just orange) or w/ the words...your call, whichever you think looks classier.