10. Boyfriend Jeans

James Devaney / WireImage / Getty
Ever since Katie Holmes married Tom Cruise, the actress, who turns 30 in December, has stepped up her fashion game and shown a strong preference for sophisticated designers like Armani and Lanvin. But when she moved to New York City last summer, her sudden inclination for rolled-up, baggy, 'boyfriend' jeans left fashion bloggers and gossip rags baffled. Holmes' make-under perhaps inspired by her new role as Broadway actress garnered lots of attention, but less than rave reviews.

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