Kelly Osbourne's Pixie Cut
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Kelly Osbourne has deep brown hair that dips into a wave into the center of her forehead and ends along the side of her temple into a generous wide curl.
Because she has a square face, I would allow for her to grow her hair out into a smooth or curly bob length, just up from her chin line. In this way, the curls or smoothness of the cut would go into that area of the facial line to camouflage the shape.
Her diamond earrings are also a help, drawing attention to her eyes and lips.
See also: More Kelly Osbourne hairstyles