Jamie, yes, it is usually done the day after the wedding. My brides will start out doing all the dry spots, walk around the resort. very similar to wedding day pictures but very laid back. Then we'll go in the water, pool, etc. One of my clients had her original wedding dress but that was it. Some bought their ttd from jcrew or even ebay. i also had a bride get one from the target bridal stuff! good luck, it's a lot of fun!