What you're really supposed to do if you're trying to express an inner feminine side is talk about your feelings rather than bottling things up. Allow yourself to be vulnerable. Express yourself, etc. Basically, take all the impulses, thoughts, and feelings that you might have projected onto women and rejected as part of your ego, and try to own them even if it makes you seem unmanly. It's not very easy to do.
I think putting on women's clothing is far too literal and concrete... it doesn't really change the way you think or feel. Also, it's symbolically distasteful... as if you were saying that femininity can be reduced to clothing and mannerisms. A very superficial way of looking at things, especially in an era where a lot of women don't wear dresses anymore.
But on the other hand, having a very strong, masculine ego that excludes the Anima and the feminine to too great a degree can lead to a neurotic desire to be released from maleness temporarily or permanently. Leading to a need to dress like a woman in order to be in a situation where you can give yourself permission to express femininity. It provides a release valve, but it doesn't solve the problem.
Basically, don't try to be more macho than what comes naturally to you. If you abstain from hugging a friend, crying at a movie, sharing your feelings, and other things that you might desire because you think they're for women and not for you... then eventually, this could erupt into a desire to be female, or act out a female role.