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Most parents understandably want their children to stand out in the crowd of youngsters who are flocking into schools these days. And for some mothers and fathers, money is no object. Lili Gross, 32, makes a monthly expedition to Fred Segal, a Los Angeles clothing shop, where she spends up to $300 on surfer shorts, Japanese print shirts and other exotic duds for her five-year-old son Brandon. Joel Stillman, 38, and his wife Renee, 38, of suburban Detroit spent $800 on smart-looking ski outfits and equipment for their son Jonathon, 11, and daughter Sara, 8. Karen Topalian, 40, bought her daughter...

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