Generally, winter boots are sized on the high-volume end of the spectrum to accommodate medium-thick socks (for spending extended time outdoors in the cold, we recommend a quality merino wool design, such as Darn Toughs Hiker Boot Full-Cushion, which are warm, tall, cushioned, and long-lasting)
Some bridesmaids may want a more modest neckline, some girls may want fitted silhouettes and others may not have a preference whatsoever, but since you have the room for discussion take this opportunity to give your girls a choice
Or, if youre cross dressing as a man, youll probably want to put on a sports bra to flatten your chest
If it comes to pairing them with grey suits, you have made the best choice
A-line petite skirts and dresses work great here, like the ASTR The Label pick below that I actually recently wore to a wedding