I used my ring sling at least occaisionally for kids as old as three, although I did get a Sara's Ride for dd when I was towards the end of my second trimester with ds (they are two years nine months apart) and found it easier for tandem wearing a toddler and an infant. The infant was in an OTSB.

My big kids are eighteen and fifteen years old and Nojo and OTSB were the newest, hottest things back then.

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