I did not start out planning to pay for their dresses. I told them I would keep the dresses under $150 and they were all happy with that. They could wear whatever black shoes they wanted.
As it progressed, we decided to have them custom made by a local seamstress, which actually was cheaper – around $100. So very reasonable.
Our groomsmen’s tuxes were $150, but Fiance was only comfortable asking each guy to pay $100, so we were going to underwrite the $50.
As it got closer, I got wind that one of my bridesmaids might be having a tight financial time, because she was thinking about not coming to the bachelorette party because of cost (just decided to become a Stay-At-Home Mom, bought a house, 7 months pregnant). My Maid/Matron of Honor mentioned it casually to me, saying that she was picking up the cost for this girl because it was important she be there.
$100 for two of the groomsmen likely also would have been a bit of a strech, and we paid for them upfront so we wouldn’t have a guy end up with out a tux and would have had to try to “collect” which wasn’t an experience I really wanted. And they are all paying for gas/rooms, since the hotel is about 3 hours out of town (we all live far apart, this is a central location that is 2 – 3 hours for everyone, it isn’t that it is a “destination”).
One day I just suggested to Fiance – “Do you think we should just pay for all their clothes?” We had room in the budget and I thought it would be a nice gesture, acknowledging how much they are spending on OTHER items for the wedding.
So we are paying for dress/tux, hair, makeup, and then about $55 each for gifts for them. They can wear whatever black shoes they want and whatever jewelry they want.
Utlimately, while the norm is to have the wedding party pay for their own clothes, I just felt like that is a tradition that didn’t make sense to me, and we had the room to pay for it and we knew it would be a thing they really appreciated, so we decided to do it. It did NOT change other plans in terms of us paying for or not paying for other items.