I don't think the T-strap is a problem as I've seen lots of fun tights-with T-strap shoe looks this year. I've been considering some T-strap shoes just for that, in order to combine comfort with a slightly more refined foot look.
I think you have to decide for yourself what kind of tights-shoe color combo's you're comfortable with. I don't think of nude pantyhose as "tights," so I'd wear those year-round. For darker tights I am less in favor of black with bright shoes but I think younger gals and do that way better, or in fields where dressing is more creative. A tonal gray skirt and tights with the pink shoes is less high contrast and could be really pretty.
You might Google up photos and see if you like the look of black or dark (navy, gray) tights and bright shoes and in what kinds of outfits.