Well, I pretty much always need fashion advice, but I'm starting to feel overwhelmed about a surprise photo shoot we've planned for my parents, when they (my mom and dad) travel with our family (me, DH, DS9, DS6, DD2) to Costa Rica this March. So far they do not know about the photo shoot. I think they'll be really thrilled, but it makes outfit planning hard. So:

1. When do you think we should tell them? If not until we're on the trip, should I try to choose clothes I think they'd like that "go" with the family's outfits? I don't want to be matchy-matchy, but my dad's a t-shirts or plaid kinda guy, so I'm just not sure what we'd end up with if we don't do any planning.

2. Help! I don't know what any of us should wear. We don't live anywhere near a beach, and today it was like 15 degrees, so I'm having a hard time visualizing. I truly don't think I have anything appropriate, so I'll likely need to purchase something. DH might have a neutral enough polo shirt, but I'm absolutely open to purchasing for anyone. I do have a dress I love for DD, and I'm kind of pulling inspiration from that, but I'm also not committed--if something works better for her, that's totally fine.

Thoughts? Advice? Direct links to the perfect dress? (I'm a pretty plain Jane dresser, so anything too far outside comfortable/casual will likely make me feel uncomfortable.)

Thanks!