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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