Do the bottom ends of these shorts roll up after you wash them?

Yes... and after you dry them too. However, after I put them on and roll the cuff down they stay put for me.

The product description list "5 pocket styling", but the product pictures do not show the 5th pocket, is there a 5th media pocket?

Yes there is 5 pockets 2 in the back ..1 on each side and a small pocket in one of the side pockets ( I call it a watch pocket)

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LeeMen's Regular-Fit Denim Short

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