In this day and age, I would look for some meetups for closeted crossdressers to come out just a bit in a non-threatening environment. I cannot believe that there are no such meetups, unless you live in the middle of nowhere.

On a purely theoretical note, yes, there is an imbalance between the genders in how playful and elaborate you can get with clothes and makeup, and indeed girls have a much wider array of options. It is an idiosyncrasy of our time - e.g. the men in the court of the French king Louis XIV spent a lot of time on their appearance, and, reportedly, modern French males outspend females on perfume. Maybe you could read books from that period to see that men still found enough worries to be unhappy, despite the flirty outfits.