Stefani,
Are you comfortable gassing up your car dressed today? That might be your dry run. You will also have to stop for a restroom break. Where will you do this? Gas station? Highway rest stop? When dressed, what restroom will you use? Make your plan an execute it. All your fears are in your head and not in the world outside.
While the drive is easy, have you ever been dressed that long? IF not, do so before you travel. It may be bothersome to you. When going out with your friend, go mainstream. It's way more fun and much easier than you think but stay away from heavy drinking places. Drunks and cross dressers might not mix well.