Most places are open air and very casual. There are a few places that I would dress for dinner, A Room With a View comes to mind. I generally only pack shorts and flip-flops for my short trips and stick to the more casual places. If I'm on island for a longer stay I might pack a sundress that can double in the evening with the addition with a scarf or wrap on the shoulders. Old Navy usually has a nice selection of inexpensive options.

that's what I was hoping to hear!

on our first trip to the island (STJ) 4 years ago I packed really cute sundresses, capri pants, nice tops. One of the first nights out in Coral Bay I wore a sundress. When I walked into the open air restaurant you would of thought I'd just come from a formal. I felt so out of place. Since then it's flip flops, tank tops, t-shirts, shorts.

If you venture over to Cruz Bay and go to some of the more upscale restaurants you may want to pack something to "dress up" your outfit but other than that it's very casual

Makes packing really easy. Enjoy