JulieJohn, I liked your suggestion so much that I had to give it a try right away! Here is the preppy blazer de-preppified with my most worn out jeans, a pair of slouchy skinnies. I left the shirt untucked, tied a silk scarf as a tie, and added oxfords. I also added my messenger bag. What do you think?

(JJ's outfit suggestion: Preppy blazer, white button down, tie or scarf tied as a tie, but loosely worn, rugged jeans, oxfords)

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