Most Helpful Guy
Women always look fine so wear whatever you want. Seriously, unless you're going to wear something completely crazy, he's not going to mind or notice and I would even argue that if he does mind, you don't want to have anything to do with him.
Most Helpful Girl
Dpends on where he plans on taking you. But an older man Since I prefer dating older men I'll tell you what I do...
1. Natural make up- No crazy colors or anything even trash the make up if you can go with out
2. A simple little black dress is fine but nothing to show too much cleavage or a high slit. But nothing with crazy colors or patterns either You want his eyes on you but not wondering to the smutty tramp next to you either. If your clothes are deep cut wear a shawl or a long scarf over the shoulders gives a statisticed look
3. Simple shoes Not sneakers but no stilletos older men do like to park a bit father away and walk to the doors to spend extra time with their dates without other guys drooling over them
4. Your hair do a simple look nothing to crazy unless you chose to put ringlets in your front bangs. But that's by preference. A simple up and down do is fine for the occasion with a nice fancy broach or hair clip in your hair to finish it off.