If the couple is very well off and wants a very dressy wedding, and most (not all) of the wedding party are struggling . what would be a tactful and gracious way for the couple to offer to help them out with attire expenses – preferably so that nobody ever has to speak aloud about dollar amounts – while leaving them pretty much completely free choice of what to wear?I would make sure you use one bridal shop or store. Before taking anyone shopping let the salesperson get an understanding of the situation. For example, before taking people out shopping select a shop that you think will work for your needs. Then let the sales people know that you will be paying for a certain percentage of the attire and that you would prefer that your wedding party not know. This can be done simply by having your friends put their portion of the payment down as a deposit and then you can pay off the balance at a later time. In order for your wedding party to ignore the dollar amounts, may be you can get the salesperson to tell a little white lie, like saying there's a sale going on or you're a special customer and they're giving you a discount for your wedding party.. things like that. Another option is to simply give everyone a budget when they go shopping. Just explain that you and whomever have set aside money for wedding party attire and everyone gets 'X' dollars. They are free to spend beyond that but you make the money available without it sounding like a pity party or something. It sounds more like you worked that into the wedding.I don't know if that helped at all but, good luck