I think Gap comes out with this every year. I didn't buy it last year and then tried to buy it on sale and it was out of his size, so I got it early this year when they had a 40% off sale. Speaking of which, just FYI, never buy Gap or Old Navy full price because they always have sales. I just login and add everything to my cart and if there's no sale, I wait and check back and all my stuff is still there unless it's out in which case it wasn't meant to be. We were able to snag a few pairs of Baby Gap jeans a few months ago for $8 a piece when summer clothes were coming out. Again, I just don't buy full price since he grows out of them so quickly.
If you live in the South then you know it's college football season and I would be remiss to not include some navy and orange gameday clothes (War Eagle!). I love Mud Pie! They have awesome sales and almost always have a discount code or free shipping. Fun fact, our son was chosen to model for them last year but he didn't get "the call" because of a lack of sample sizes, etc. We still love them :) I think their clothes run a bit on the small side so I have always sized up.
Can we just talk about that jacket please?! How cute! I am loving the new Cat and Jack line at Target. I love almost everything and they only carry a few of each size in the store so you maybe feel like your kid will look original? Everything has mostly been sold out in the bigger sizes when I've been so I got a couple onesies the last trip that my husband picked out. If he likes it, I'm like yeah let's buy it! :) I think we will need to get a jacket this year, but maybe a fleece or sweater will do. I'm holding out hope he'll need that jacket though ;)
I bought one pair of Christmas pajamas from Mud Pie already and tried to buy some Carter's at Target. They were already sold out in the store in all sizes except big kids. What the heck - it's only September. One thing I will not get used to in kids shopping is having to be two steps ahead of every holiday. Last year I missed the boat on special Christmas pj's because I waited until November and then couldn't find any good ones. Silly me! My son has been wearing Halloween pajamas since August because by golly, I bought those suckers when I saw them in his size!! Never mind that I had to crank the air down because who wears long sleeves inside in the South in the summer.
I hope you other boy moms have got some good ideas and maybe found something new you haven't look at before! Happy shopping!