I recently went on work/vacation trip and was slightly appalled at what I saw some women wearing (or not wearing). There were plenty of haltertops with no, ahem, support to speak of. Not a pretty sight. However, I was trying to refrain from being my usual judgmenty self because I totally understand the concept of not dressing as you usually would when you are on vacation. In fact, I have a whole separate vacation/resort wardrobe that I would not wear when I'm at home. Dresses a little too short for a night out, maybe a sexy little top that I'm actually too old to wear in my real life, etc. To a degree, you can have a different style while on vacation and get away with wearing something you wouldn't ordinarly wear around town just in case you run into a co-worker, teacher from your child's school, your priest. But there are still some rules:
1) Wear the proper accountrement - please, on vacation or otherwise, no one wants to see the girls hanging to your knees. Remember the humidity if you are in a tropical climate - clothes will stick to your body. The right bra and Spanx provide the requisite smoke & mirrors to make that outfit fit just right.
2) Don't assume that tropical prints are "vacation" clothes. Use sparingly and not at all if possible. Ick.
3) Don't pair a nice dress/outfit with FLIP FLOPS. Dressing for dinner on vacation does not include flip flops. Period. If you are wearing flip flops, then you are eating, not dining, and are at the wrong resort.
Unfortunately, our usual plans for vacation this year fell through and my vacation wardrobe won't be visiting Mexico. Maybe someone could send it a postcard?