Samantha you look good..especially your overall face and shape.
Your wig is a big tell though...this is a toughie..you have to it just right on your head and keep it there..i think the overall shape is perfect for you btw..
Also, I think you would look spectacular with those boobs and your broad shoulders in something much more long and flowing around your top side....there are many outfits at lane bryant for example where you get a cute tank top, and then a soft shawl/sweater to go over your shoulder and arms... this type of top would go really well with tight pants or a skinny skirt..
If you are serious about passing, i think the outfits you are showing will make you not pass. I know how fun it is to dress up for yourself, but save those outfits for times when you don't care about blending in,
My only other thought is that I have no doubt you look great enough to blend in very well EVEN IF YOU DON"T PASS TOTALLY... if you get clocked a couple times, don't let it get you down, and you may find that there are moments where this happens that are wonderful and positive...i hope you have a great time