Take a look at the women you come across in your life. What do you notice? Do you not notice that every woman looks differently from the rest and yet they look feminine?
The core essential of femininity is being individual and expressing your own individual femininity. This is how it works.
The good thing about femininity is (from our perspective) is that you don't have to be female to be feminine. Dustin Hoffman, Robin Williams and Patrick Swayze have all been transformed into feminine women in their careers.
Be creative, just like an artist. Artists start out with just basic shapes. Knowing the basic shape of your face and body is the first step. The shape of your face will determine what hairstyles and wigs will suit you, and the shape of your body will determine what clothes will look better on you. You can get lots of ideas off the Internet. Just google 'face shapes' or 'body types' and you'll see the pages come up. Explore.
You also have to remember the three key words which are
LENGTH
STYLE
COLOUR
This applies to clothing just as much as it applies to stuff like wigs, jewellery, and apart from size is the most essential information a woman thinks of when she's looking for things to present herself in.
Let's take for example skirts. What's the first thing you need to think about? The SHAPE of your legs. Do you have long legs? Short legs? Do you have bandy legs? Are you knock-kneed?
The shape of your legs will determine the LENGTH, STYLE and COLOUR of the skirt which looks good on you. You'll see that skirts come in different lengths - mini, micro, knee-length, long, maxi, and calf length. The style of the skirt can be a pencil skirt, A-Line, flared, gypsy and so on.
Same thing again for tops, dresses, wigs, accessories, anything you can think of. They will all be defined by those three words - length, style and colour.
You can go back and look at the women you come across and see how quite often their clothing and accessories will match when it comes to these three things and they will also be dressing to either accentuate or camouflage their shape.
Colours of course have to match, usually between two or three. Often there is a primary colour such as black, blue, or brown with which brighter colours are worn.
For example colours match usually between a coat or jacket, handbag and shoes, which are all the same colour, and quite often this is a primary colour worn by the woman - such as black, brown, grey or blue.
Hope this helps.