a Madewell Share definition Flag A Madewell is where a guy declines to take breaks with his piers in order to perform sexual favors for his new boss I think Chris is doing a Madewell instead of taking breaks with us now. a Madewell by C.Lynch August 7, 2008 0 0 Get merch Get the a Madewell mug. Buy Now — $32.95 See more merch