For me that has meant simplifying my base wardrobe with mostly solid colour tops and using accessories like scarves, jewelry and cardigans to switch up my looks. It makes choosing what to wear so much easier for those of us who aren't really clothe horses to begin with. Yes, I want to feel feminine but comfortable which also means wearing shoes I can spend hours in although admittedly I have one pair of killer heels I reserve for that event I might one day attend.
There's a lot more to me than what I wear so I don't want that to be a distraction. Hence this summer I will be often sticking with a simple T-shirt, shorts and ballet flats.
It's funny; the more I have felt comfortable with my being trans the more that has meant focusing on the internals rather than the externals.