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Before I even get into this I have to link the Tumblr so you can bookmark it.
WTF is Michael Jordan Wearing
The theory goes that Jordan has so much money and is such an iconic figure that he can wear these outfits and get away with it.
I have a better theory I think Juanita use to dress him and once they got divorce he was left to dress himself and you see results.
His new lady should take him to Marshals or TJ Maxx, refresh the gear at discounted rates.