In His Father's Shoes (1997)

When his father (Louis Gossett Jr.) suddenly dies, Clay Crosby (Robert Ri'chard) is devastated. It seems he'll never be able to get over the loss. But everything changes when the boy puts on a pair of his father's wingtip shoes, which magically bring him back in time to experience his father's early life. As Clay gets to know his dad in the past, he gains an improved outlook on his own life. And, by changing the past, he wonders if it might be possible to create a better future.