My son (also a Jack) is 14 months and still rocking some footie jammies. I stocked up at Old Navy, though we also got lots of hand-me-downs from Carters and A Children's Place. I'm like you with shopping. I HATE doing it for myself, and enjoy it only a bit more when it's for my son. I tend to stare at things, not see what I want immediately, and get frustrated and leave. My secret has been my mother-in-law. Every time Jack outgrows his clothes, my husband places a call and casually mentions that we have no clothes that fit (Oh, he's getting so big! He's grown out of all his 18 month clothes already!) Before you know it, she visits with a huge bag of new stuff. It's fantastic. It also helps that we are friends with two couples who have had boys and are now done with child rearing and happy to pawn off all their old stuff on us.