Welcome to JWN! Just in case you're not aware, the vast majority of people have a colorful past. Please don't allow yours to guilt you into pledging your allegience to a high control group! Your open mindedness with your kids will NOT fly with the Watchtower. Take some time to research the organization, and analyze what it is about your colorful past that urged you to study with the jws in the first place.
Your reservations about being baptized are correct. It's very hypocritical for your study conductor's husband to object to you wearing the very same clothes that his wife and daughter wore. Maybe he's just a dirty minded fool who looks at you through a different lense than he sees them.