Choosing a bridal party actually really stressful for me. How do you go through your life and choose a random number of friends to be the ones who stand up beside you as you get married?! And really, when you think about it outside the context of the historic tradition of maids and men, it's a little obscure... "OMG, you're my best friend, want to stand beside me as I go through this intensely personal moment with that guy standing on the other side of me?"
The way we made it work for us was that we chose couples to stand up beside us. Each of these couples (married, of course, it would have been rather awkward if they had broken up between buying the dress and walking down the aisle) is remarkable for their own reasons, and Scott and I have learned so much from watching their relationships grow.
And because each of these relationships is unique, we didn't want them all standing up there looking like cookie cutters. I selected a colour for the dresses, and told them to go wild (admittedly, it wasn't as easy of a task as I thought, so I thank them for having to negotiate different names for different colours with different brands). I even had one girl decide to make her own dress... try and guess which one!
As for the boys, we knew it was likely going to be a beastly hot day (which it was), so going for a full tux seemed excessive for an outdoor wedding. And it turns out renting only parts of a tux was just as expensive as buying pieces, so we had them hit up their local Le Chateau for a pant/vest combo. Our stipulation was the shoes were to be black, the shirt was to be white and the tie was to go with the dresses, but other than that, they were free to do what they wanted. While the differences in ties etc. was certainly more subtle than the girls, I loved seeing who went with stripes, paisley and solid! (There was one more rule: no neck beards, which I think is a good rule for every day life).
It was great having such supportive friends surrounding us and looking good too!
(The homemade dress? The bubble skirt and cropped jacket!)