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Each stylist has two "looks" they specialize in. The other stylist on the hire menu is the "cute/pretty" stylist. So if you want to train all of those looks then you need two stylists.

Well, they're certainly not working that way - all of mine are "cool/sexy" and they're still working on "cute" and "pretty".  And they're only leveling on "cool/sexy", regardless of the type.

And if they're meant to work that way, the difference in starting levels makes even less sense.