^ The thing that came to mind for me looking at your chart is you have a very strong Capricorn influence in your chart (I think you have 4 Capricorn placements if I recall?). You mentioned hesitance to dress the way you would really like, and my thought was that this Capricorn influence may be making you care what others think.
It's also interesting that you're a double Sagittarius (which would give you a tendency to be very frank, I also have Sag rising), but with the Moon in Cancer, that would give you a pronounced tendency toward privacy & not revealing yourself, plus you've got fire vs. water tension there as well. (I do too, with Sun in Leo and Moon in Pisces.) I feel that this kind of 'conflict' makes us more complex, but also stronger, because you've got all these different 'weapons' in your arsenal.
I've worked for a Scorpio before, and my natural fiery tendencies weren't really what I needed in that situation. So I drew on my Mars in Scorpio ... I think having a diverse chart like this can perhaps make life a bit difficult as you get a grip on it all, but then it makes it easier for you to 'survive' in different situations and relate to others in a variety of ways.