You mentioned that God spoke to you and told you to do away with all vanity in your life. I'm not sure if you meant that God literally spoke to you or if you inwardly felt a need to be less vain and sensed that this would be pleasing to God .
Either way, it seems to me that going to the great lengths that you've described, such as wearing a head covering everywhere thus making yourself stand out from others in an odd way, could in itself be a form of vanity or narcissism. Be sure that your motives are pure. It seems to me that you could on some level, be trying to draw attention to yourself and to what a good and righteous woman you are, compared to all those other vain make-up wearing ladies out there who go around with their heads uncovered.
Thinking that your personal dress and grooming is so important to the God of the universe, that he would speak to you about it and that he absolutely needs you to go around with your head covered up, could be a form of narcissism. You may think that you are focusing on God but instead you may be focusing on yourself and how godly doing these things makes you feel and how pious this makes you appear to others.
JW's (and others) tend to strive for balance when it comes to dress and grooming and their personal actions. They also don't believe that God speaks to individuals directly (especially women). To tell you the truth, JW's won't likely be impressed by your head-coveing and lack of make-up. You may be inadvertently sending them the message that you think you are more godly and less vain than they are. Rather than being impressed, they may think you're not a spiritually balanced person and will likely view you as spiritually immature and not ready for baptism, which of course is their ultimate goal when they study with you.
You mentioned that you are new to Christianity and you said something about having changed and no longer focus on the "layers of makeup" you are wearing. It seems like you may
have gone from one extreme to another. This is a common thing to happen to newbies.
Why not strike a balance? Avoid the "all or nothing" mindset that people often get when they embark on a new religion. If you formerly wore a lot of makeup and or were spending an inordinate amount of time, money and thought on your grooming, why not reel it in a little? Choose an easy hairstyle, wear a dab of makeup if you want to and wear more practical clothing that won't be hot or encumber your day to day work and activities the way the clothing you've described, might.