They're both cuddly soft teddy bears with almost the same learn to dress features of button, zipper, snaps, laces and velcro™.
They are both bright and colorful.
But there are two major differences:
Cubby Bear has the words embroidered on him... Tie me, snap me etc... so he has the 'starting to learn to read' function. So maybe a bit better for the two and three year olds.
Teddy Wear is just much, much bigger - bigger button, huge star on his chest as a zipper pull... bigger shoes (with both laces and velcro fasteners so even if the laces are untied the shoes won't fall off.) etc. All those bigger parts and pieces make him easier to 'dress.' So maybe a bit better for the younger 18 month to 2 to 2½ year old range.
And finally, Cubby Bear is a 'carry me' size, while Teddy Wear is a 'cuddle me' size.
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