How to Dress Like a Mom (Not a Regular Mom, a Cool Mom) 1) Choose your athleisure. ... 2) Embrace all fifty shades of gray. ... 3) Let those tops flow. ... 4) Have a really good pair of legging capris. ... 5) Apply dry shampoo. ... 6) Simplify your accessories. ... 7) Have something on your head. More items... Aug 17, 2017