My biggest struggle so far with wedding planning has definitely been Bridesmaids dresses. For the style of wedding we are having, the dresses have been a challenge, mix that with the fact that I want my bridesmaids to be happy and NOT poor, and well that makes for a rough time for any bride to be!
Let me back up for a minute and tell you a personal experience. A friend that was very near and dear to my heart was getting married once and she forced (yes, forced) me to buy the bridesmaid dress a YEAR in advance of her wedding; now the year part isn't so bad, I understand how exciting it is..the part that gets me was the cost of the dress $250! Yup, she made me drop $250 on a dress a year before her wedding...For a wedding that she ended up calling off. So I was left with a hideous dress and out $250. Anyway, I remember my resentment over being asked to shell out $250 for a dress that I would only ever wear once. I don't want to do that to my friends! I wouldn't dream of it! And that is what has made finding pretty but affordable dresses SO difficult!
I searched sites like Lulu's, Charlotte Russe, Forever21, Windsor, basically all affordable dress stores that I could think of, and came up empty handed each time. So bummed! That's when, but truly lucky circumstances I came across the fact that Target (YES! target!!) sells super cute bridesmaid dresses, for only...wait for it...$69.99!!! ahhh *cartwheels*