I would-- if I had the right fabric, fit, footwear proportions to look dressy and sophisticated and not just what I think of as holiday party. Really, a HEWI for me is a killer almost- formal pants outfit since I freeze at indoor galas and it seems easier to pair a great jacket with pants than with a dress AND because I feel there are more footwear options that are remotely comfortable.
In some ways I think the goal is ( for me at least, with pear issues) is for pants to be very appropriate style and fabric and flattering fit, but black, which is more forgiving AND formal, but not the star attraction, so that a killer top and or jacket in face- framing/ flattering style and color/ sparkle/ glam is the focus.
