The expert says you can lean even more into minimalism with dark blue jeans and a light-blue denim jacket—or vice versa. "Opt for oversized head-to-toe for a relaxed, cool-girl feel," says Gerard.

Katie Holmes is a master at transitional dressing; known for her approachable, effortlessly chic looks, there is no one we'd ...

or even black denim paired with a lighter wash," you can take her expert tip to a place of even more minimalism with dark blue jeans and a light-blue denim jacket. "If you do want to go all-or-nothing ...