Having high quality well-styled hair is a very feminine signifier and can really enhance your overall look. It can also be used to frame your face in a way which shortens or thins it and to disguise certain features.
You need to identify your hair type first and consider potential hair styles based on what is possible with your hair. Curly hair can be straighten and straight hair can be curled to some extent but it requires more equipment, products and time.
It can take a while to get inspired with a desired haircut but you will need to grow your hair out and take good care of it either way by conditioning and detangling it. Certain lengths will allow you to create multiple looks with different styling so don't feel committed to just one way of doing it, consider things like how much effort is it to style, how you would put your hair up, how you might wear hats, how would you deal with rain/wind and how you would sleep with it.
Use Pinterest and look at street fashion and various media to get a sense of what to try. It's recommended to go to a good hair stylist during your transition and to get professional personalized advice on how to cut and style it in a way that works for you.
Using a hairdryer for volume is an important technique for a lot of haircuts