I can tell you some of my experience, but I'm not sure if that will help you or not. I don't consider myself a transvestite, just an androgynous boy. I don't tuck or wear feminine underwear or fake boobs, because they just don't feel right on me. That being said, I don't own any mens clothes (except underwear... but it's just silly to count that), and I'm hella good at makeovers, so I'll help as much as I can!
Learning how to do good makeup and hair is something I wish I had done much earlier. Makeup takes a lot of practice, but YouTube is going to be your best friend.
Lisa Eldridge has the best makeup tutorials on the internet - period. The best tips that I can give personally are:
-Less is more. No really; way, way less is more. A simple look done well in 10 minutes will look much more flattering than layers upon layers of foundation and loads of bright eye shadow.
-Learn subtle but effective contouring.
-Well groomed eye brows will get you more compliments than anything else.
-When covering facial hair, use neutralizing colors rather than trying to cover it with loads of foundation. For instance, I have dark hair, so under my foundation I apply a liquid/cream orange or red color (can be anything - lipstick, lipliner, cream blush, cream pigment, color-correction primer, etc.) on my upper lip and chin, where I get the most regrowth. The orange counteracts the blue tones that make up the "shadow", and hides it completely. It's important to note, though, that this is better for short periods of time. My facial hair grows back pretty quickly, so even though I use this method every day before going to work, I will still have a tiny bit of 5o's after 8 hours or so, simply because the hair will grow through the makeup.
-Invest in good makeup that works well with your skin.
-Use brushes, not those weird sponge applicators that come with shadow. It's a lot harder to use those than it is brushes. Also, good brushes will last you a decade if you take care of them.
In terms of hair... hair is just difficult. For me at least. I hate wearing wigs, and weave never lasts on my head, so I'm just now starting to have fun with it. If you don't mind wearing wigs, though, that's your best option. You can have endless looks and still keep your short hair for more "manly" occupations, if you need to. I will say, though, that cheap wigs are easy to spot. We all can't afford a $4,000 lace front like Beyonce, but investing in good hair that will last you a long time, and learning how to take care of it (again, YouTube!), is always the best route.
Finding clothes can be frustrating. Even though I don't wear fake breasts or padding of any kind, my rib cage is very broad, and is often times too large for clothes that fit all the other areas of my body. Most days I simply wear a t-shirt, jeans, my leather jacket, a scarf, and some fierce shoes. It's all about the shoes and accessories for me, which I why I keep the rest of my outfits simple. My style is somewhat edgy, and most of my clothes are black. It's all about finding what works for your body and what kind of styles you like.
I'm not sure if any of that was helpful... Good luck though!!
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