Louis Coraggio, a health coach and the founder of Body Architect and TrampoLEAN, says good workout shoes should feel comfortable right away — they shouldn’t feel as if you have to break them in.

The Coach Outlet’s latest sale includes deep discounts on classic styles, like the men’s Banks Boot, now available for $83.40, down 70% from its regular price of $278. The chukka-style boot has a ...