I'm directing this more toward dressers who don't dress all the time. I understand trans that dress often can't be bothered spending hours getting ready!
I've always been a tinkerer. As such, I'm never satisfied with Sherry's looks.
I'm always fiddling with her looks, figure, outfits, and trying new and inventive ideas for her story personas.
But, I know lots of CD's who r content to simply throw on the same things time after time. Some make their look more fem over time. But, others r quite happy with their obvious man in a dress appearance year after year. Wearing the same style dress, wig, etc., etc.
R u a creative dresser? That strives for different looks? Or, just blissfully happy throwing on whatever u have at hand?