If being bold is always shot down, then how do new fashion trends get started? If there wasn't new trends there wouldn't be past season tack & clothing. I believe we shouldn't be afraid to be innovative in today's hunter classes. There are so many new colors and designs to chose from.
I see a lot of stuff in the Hunter ring that shouldn't be. At a recent derby that featured tragic riding by and large or good rides with too-young riders, I saw the women, as I think the class was entirely women, in really loud attire (save one class act pro). Large blinggy belts, loud pastel shirts and the like will not win you in favor unless the majority of the horses execute weak trips. I also don't like seeing hunters without gloves. Spurs should not have bling on them. The brown jacket/hat combo is not nice but on a fair blond or redhead it can work. I don't recommend it but I have seen it work aesthetically. I like the white or light blue shirt, a pastel pink or yellow shirt is nice too, seafoam on the right person--all these shades are very, very light not bright. Show off your hunter, not your fashion slants. Make your horse look incredible and ride him/her with the dignity the sport asks for :) And have fun!