Just had my fitting yesterday at DB (holy hemming and 22-point bustle) and had my mom take a look at some dresses. She hated every single one, and to be fair, most were ugly in that jersey/chiffon/loose but oddly clingy fabric that isn't the most flattering for a woman in her 60's.
Additionally, my mom has had very low self-esteem her whole life, doesn't want to show her arms or legs, and is just overall very hard to shop for dresses with. In total contrast, my FH's mom is fairly young and so are the rest of the women in his family (mid to late 40s) who get dressed up in cocktail attire and go on party/fancy outings regularly so I don't want my mom to look like she's older than she is or give off a grandma vibe (and she looks plenty youthful so she shouldn't be in something that makes her look old!). I just feel like she's closing herself off/is already dreading this whole thing because this experience (looking "pretty"/getting dressed up) is something very out of her comfort zone. Our wedding is in late May and my mom tends to run warm/hot so I'm thinking of using that as a way to get her to try some different styles. It's frustrating because she won't so much as try a subtle high-low hem and I feel like she's purposefully being difficult (example: yes, mom, that ribbon is for cinching the waist - what do you think it's for; that dress off the rack is obviously a size 12 but PLEASE just try so we can gauge the style!!!).
I'd appreciate any help or tips you all have, or anyone who went through something similar. And of course, what are some good places to find dresses? We'd like to keep it under $300 so some of the higher department stores are out of the question.