It's great to know that you want to grow and learn in the areas of self esteem and modesty. Do you have specific questions or just want to know some advice in general?
If you haven't already, I'd recommend you check out these pages at this site....
The last link is a modesty survey given to guys and their responses to just give you an idea if something would be considered modest to a guy. This is the section on makeup but you can browse the other topics on clothing as well.
Let me know if you have any other specific questions!