Well, this might work but it would require some compromises to be made and it really depends how You feel about those kind of compromises. I am on somewhat middle-level dosage and those who see me every day and dont know - they still have no idea, though sooner or later You are bound to slip up somehow. The most difficult thing is posture, mannerisms and all those details, but these could be dealt with in shorter periods of time by observing Your behaviour and keeping it within "acceptable male behaviour".
The problem is with those people who You meet for the first time and when You kinda mix Your social life with them and those who knew You before but are kinda "in the darkness", because sometimes the former ones start asking questions behind Your back which makes the latter ones kinda wonder and look at You differently.
Also, depending on Your genetics, age and other factors, there are going to be inevitable male fails and sometimes they happen when You are least expecting them (for example, when wearing 100% male casual attire), but You get to learn how to deal with them eventually.
Sometimes I need to present professionally (and I cant get away with smart casual only) and I do look a bit weird in power suit now, but usually people dont really care and You can get away with explanations like being on diet, growing Your hair out etc etc etc. If You are over 40-ties, You can always joke about male middle-age crisis and that You are now treating Your skin with moisturisers, dieting, exercising and whatnot - those are kinda contemporary stereotypical behaviours of middle/upper class male who is experiencing middle age crisis and they are kinda convenient to exploit for Your needs

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