Self-Proclaimed Dork: How Not To Overpack?

I really hate trying to decide what to take on any trip. I overpack all the time. I take three weeks worth of clothes and only need 5 days. This Summer, in three weeks really, I'm going to Oak Island with my entire family; 40 of us. I need cute outfits to wear out to dinner or a bar, but I don't really have any clothes worth taking right now.

My main issue with Summer trip clothes is I'm a curvy girl. I recently had shoulder surgery and put on an extra 20 lbs. I'm not any bigger than a size 14 but short shorts, tight tanks, and maxi dresses don't look right on me. I'm going to the beach for 7 days in a few weeks and while I've lost 5lbs recently, it's still hard for me to find weather appropriate, cute clothes to wear. This great site, hellogiggles, put together this really cute "What To Pack For Vacation" article. But as stated before, I have a booty, boobies, and thick thighs. I've always hated short shorts. My legs are long so even a 5 inch inseam looks like a short short.

So I've come up with a few tops, bottoms, and dresses that would work for a girl like me. It's a crude graphic but it works for what I'm trying to show. I'm actually getting a few things in the same style of the graphics. What I've selected are: bermuda shorts, capris, two dresses to be worn as a coverup/sundress, and a few looser fitting tanks. I kept every item under $100, and most are under $50.