Cole Haan has a cult following for its stylish and insanely comfortable footwear. This sleek leather tennis shoe is supported by a lightweight EVA foam sole. Discount will vary by size, but you can get these for for up 51% off the list price right now. Get it in tk colors and men’s sizes 7–13, with half sizes and wide options included.

Sam has covered every Amazon sale for the Strategist the past two and a half years, so she knows when a deal is truly a good one (and when Amazon is just inflating the original price to make it seem like a better discount).