In the season 5 finale, Jacob visits James at James' parents' funeral. Young James is wearing shoes that are much too big for him. They almost look like they might be adult shoes. In season 1, Kate takes a pair of hiking shoes off a dead body. A quick search of Lostpedia shows that Christian was wearing white tennis shoes with his dark suit in his coffin, a white tennis shoe was hanging from a tree on the island, and Christian is often seen wearing one or both white tennis shoes. A man with red shoes was killed in "Flashes Before Your Eyes" in Season 3. Charlie hid his heroin in his shoes in the first season.
I'm probably missing some instances, since I'm not really a LOST fanatic, but I'm surprised I haven't seen the "shoe" discussion milling around. Do James' shoes have a special significance? Or is it just an indicator that as a poor kid, he might have had to borrow shoes for the funeral? The shoes are similar (plain black oxfords) to the pair that Jack got from his grandfather to take back to the island with him. Could they even be the same pair?