I think the engagement photo shoot might be a guy's worst nightmare. At least, for my guy it was. He was skulking around the house hours before we were supposed to meet our photographer and snapped at me when I told him that his mom suggested he wear a button-down shirt. In the end, he wore his usual uniform: white v-neck t-shirt, jeans, and converse.
Originally, I was going to wear a red dress from Alice and Olivia. But, anyone who knows me knows that I hate the color red and just started working it into my wardrobe last year. When I told my sister about my outfit plans, she gawked and then suggested that I wear something I would be guaranteed to like next year and better still in ten years. And so, the day before the shoot I was rummaging the racks at Bloomie's looking for a suitable alternative. The lesson for both me and him: wear what you're comfortable in because the shoot is awkward enough!
Even though engagement photos are cheesy by nature, and the shoots are more than a little awkward (unless you're a professional model or something), I definitely recommend going through the experience with the photographer. There are a couple of really good reasons:
1) Up until the engagement shoot I was a little worried that I made the wrong decision. I mean, there are just too many choices out there. And I was having a little case of buyer's remorse...but once we met the photographers, all my doubts dissipated. The ladies were super relaxed and made it really easy to just let go and be ourselves. They also knew exactly what types of shots to take and how to get us as relaxed as possible with each set-up.
2) I can't imagine having never worked with my photographer before and then allowing them into one of the most intimate moments of my life (my wedding). I mean, there are so many super intimate moments on your wedding day (the first time you see your groom, getting dressed with your girls, having your mom there, walking with your dad/mom, etc.) and it seems to me that it would be best to have someone photographing you who you have at least worked with once before. I can't imagine some stranger rolling up the day of my wedding and trying to capture my best moments.
As a side note, I have a good friend who opted not to do an engagement shoot before the wedding and ran into some of these exact problems on the day of. Since she had never met or worked with the photographer before, he had no idea how she and her groom interacted and how best to capture it. They also felt more awkward having someone they didn't know witnessing their intimate moments before the ceremony and stuff.