I would definitely transition anyway.
Clothing is meaningless and there's always a way around social conventions. Before I "woke up to myself", I was trying to work out a way to dress feminine in public (I didn't know why). It occurred to me that in some past eras, men's fashions were a bit frilly or soft. I swear to god I was going to web sites that sell historical clothing (of very high quality) and checking out men's clothing from other eras.
There are a lot of men's fashions throughout American History that would give me that feminine feel. Long coats, stylish shirts, scarves (for the neck & the waist), BELL BOTTOMS (no joking), cowboy or range type items, pieces of some military uniforms, and it just goes on and on. There are lots of feminine items that are accepted as masculine in other times and people today seem to accept them.
Men's ponchos, hats, & etcetera & etcetera, my friends.
If you go European, it gets even wierder. Robin hood type articles, medievel things, renaissance items, anything French.
I don't think it works the other way, though, if a genetic female wanted to look for masculine type women's clothing amongst historical trends, they will be disappointed.
Remember, I'm trying to get around the new rules that Melissa's goverment arbitrarily imposed upon us peasants.

Love and smiles,
Rebecca Fog