Similar to the popular belief that it's uncool to wear shirts tucked in is the general consensus that it's uncool to wear a sweater that doesn't tightly hug one's every curve. Baggy sweaters are associated with nerdy middle-school girls who are self-conscious about "developing."
I think this notion is passé. A baggy sweater looks refreshing and chic and makes its wearer seem relaxed, down-to-earth, confident, fun, and comfortable in her skin.
It's important that an oversized sweater have some kind of banding at the bottom so that it hugs the body there instead of flopping all around. And I think it's best to keep it simple. A men's small classic crewneck sweater in a solid color should work. But please none of those terrible thick waffle-knit sweaters that are trendy right now.
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