I just put them in nice looking casual outfits (e.g. khaki pants and a polo shirt). I tried to keep them in colors that look good together, but nothing too matchy. We tried to get photos of the two boys together last summer, but Connor wasn't having any of that. He was super cranky and we could barely get a smile out of him, let alone have him pose cutely with his little brother. We ended up just getting separate portraits of the two boys. Hopefully next time it will go better.
My friend had some pictures taken of her boys at the Picture People and she dressed them both in jeans and white t-shirts, barefoot. They were very casual and playful and the pictures look amazing. I wouldn't worry about the poses because the photographer usually has some good suggestions.
My son was never very cooperative when it came to taking professional pictures when he was younger so I just gave up and now we just do the school pictures. Once Baby # 2 arrives, I'm hoping to get professional pictures taken of both of them together.
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Picture People usually recommends matching or similar outfits. I didn't match them exactly but I usually dressed them similar colors and made sure their pants or shorts matched. The barefoot pictures are so cute with babies! PP is very good about finding cute and candid poses and they use a lot of props in their pictures.
I always did walk-in sessions when the kids were babies because their schedules were unpredictable. We'd go right after lunch or nap when I knew thay would be more cooperative. If you decide on walk-in, they get busy during holidays so my suggestion would be to go in the next couple weeks or wait until after Father's Day. We've gotten the best pictures in the middle of the summer or in January because that's when they are the least busy and the photographers are able to spend more time letting the kids warm up.
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