Do you mean in private or in public? I think its a tricky question. In private, yes definitely. In public, you should be aware of the repercussions if you don't pass "or blend in." This could crush your confidence if people start pointing and laughing, which apparently happens a lot. I mean will you pass okay, or at least ok enough that people won't say anything, they won't know for sure and hence, stay quiet. If you obviously look like a man, then you will need a lot of confidence. I dressed pretty andro or femme a long while before HRT but I just wore women's clothes that were androgynous cause I liked the style and fit. I pretty much have to wear women's shoes or insert lifts in any men's shoes I buy to take up the empty space. I'm like a size 5.5-6 in men's.
In the end, do what you want to do, but I wouldn't do anything you're not comfy with as it could hurt more than help. Really, it depends what typr of women's clothes are we talking about, like sundresses or form-fitting tops and skinnies or like reg tops and boot cut women's jeans. You could wear the latter and no one would know the difference while at the same time becoming used to the idea.
Question: how long have you known you are trans? You seem young by your posts, so remember, this isn't a race. It's a marathon and the end goal is to finish to not to sprint and then run out of gas and quit.
