Petite celebrity cook Rachael Ray has such a sunny personality and wears figure-flattering wrap dresses with V-necklines so frequently on her TV show that we were surprised to see her wearing this shapeless gray dress. While not a traditional trapeze dress because of its seaming, this dress certainly has the shapeless quality of a trapeze. Although wearing monochromatic colors is usually a great way for a short woman to look taller, this look isn't quite working for Rachael.

When she wears boots, she usually wears the hem of her dress over the top of her boots, and that styling trick helps give her more of a vertical line. But with this outfit, there's a gap between the boots and dress and darker gray legwear breaks up the vertical line.