3. Skip-It

AVERAGE OG PRICE: $12.89 (new)

MIGHT FLIP FOR: $120 (vintage)

It was the infamous 1990s Skip-It commercial filmed at Ravinia elementary school in Highland Park, Illinois that helped make this toy a success. The advertisement played during children’s programming. Kids had to have it when they saw that apparatus swinging around other kids’ ankles.

Skip-Its are still available for sale, but definitely lost a bit of its cool factor with children today (iPads are the new hip thing). However, collectors might buy your old Skip-It for $120 on eBay. Might have to be in the original packaging, however!