Thanks for the feedback y'all! #3 is in fact peekaboo, I didn't know that would be considered inappropriate, but I'll look for another option. Also, should I just get rid of the sweaters?
Yes, for all that's holy (fun with puns), do not wear that. Remember, you're impressing girls, not guys.
On a side note, am I showing my age when my first thought was how someone in that dress would hide their stretchmarks?
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