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The premium baby gear is more for the parents than for the kids. Typically speaking the kids aren't going to feel much of a different sitting in a uppababy seat vs a cosco one except the uppababy is probably easier to buckle/unbuckle for them.
For the parents it would mean how well the stroller handles bumps, can you one hand close vs requiring two hands. Can you one hand lift it into the trunk or backseat footwell. A car seat might be how easy it is to undo and transfer, also the question of whether a full steel construction seat being safer than an all tic tac plastic one.
Clothes doesn't matter though, from infant to 6, chances are they are growing out of the clothes more often than wearing them out.
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