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What would the other toddlers say if you sent your baby out in a trucker hat and Uggs? They'd point and laugh, and with good reason. That's why you need to help your little one look fashionable. One day, when they can finally make complete sentences, they'll thank you.
Just because they'll rip off their pants and try to use them to capture the cat is no reason not to at least TRY to keep them looking fashionable!