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Well, I never had this problem with Connor! He was always tall and chubby to start then thinned out. But never had an issue with clothes fitting him! He sailed from one size to the next with no problems. Now with Peyton, nothing fits her well! The NB stuff is good in length, but she's stretching it sideways (and we only have like 5 items in NB size lol). I've found that certain 0-3 month clothing is a good fit, but anything that says "3 months", like Carter's especially, is HUGE on her! The length just keeps going and going, it's ridiculous!! I have like 6-8 outfits that fit her well that I keep recycling her through lol, poor girl! I have a closet FULL of clothes that don't fit yet!
Carter's always runs big. Bourne usually would fit into them as a transition between sizes. Sosa he was almost ready fot6months, the 3month Carter fit him.
You may find that there are certain brands that work better. For example-about the only jeans Bourne can wear are old navy/gap skinny fit. All other 2T slide off his non butt but 24months are like Capri pants.
years ago with my boys (who ar 8 and 10) - I found that Gap was true to size and that Old Navy ran wide (either that or my boys were skinny and that is why Gap seemed true to size). You may want to try Old Navy though.