JulietAlyse: I have let me hair grow for about 4 years now and it is almost mid-back. I have had it cut and styled in a feminine way about 3 times now to go out but just put it in a ponytail for everyday drab wear.
I also have several wigs and I like being able to go either way. For outdoor activities and everyday wear I can wear my hair down and styled or with a feminine cap. For dressier events I can choose a wig.
I have to say that my wigs feminize me much more than my real hair. Going to a wig store and trying on different colors and styles makes all the difference in the world. My most-used, go-to wig is one that I probably would not have selected just seeing it online or in a catalog but trying it on and seeing how good it looked on me amazed me.
You will be surprised with the results.