I use the words “shove-it-on-and-go” because the slip dress has always functioned as a sort of low-effort shortcut into cool: in part because the design was originally intended to be worn as a boudoir-ish undergarment.

Holmes walked around her Manhattan neighborhood in an outfit that could have come from her Dawson's Creek days. It couldn't have been more minimal (for her): a '90s black slip dress with spaghetti straps and an exposed raspberry bra peeking out from underneath her dress.

Katie Holmes kicked off her jeans for a slouchy summer dress this week, as temperatures reached the 80s in New York City. And this week, she pulled a style cue from the mid-’00s, nonchalantly layering an easy black slipdress over a red and pink tank—their spaghetti straps clashing and twisting in a way only Holmes could pull off as cool.