
After studying Katie Holmes's best outfits professionally for nearly a decade, I can definitively say she thrives at the understated-yet-elevated errand look. Give her nothing but a sidewalk, a Reformation coat, and Adidas sneakers, and she'll build a weeks' worth of coffee-run outfits—making each one feel special with a colorful pant or a trendy belted bucket bag. Send her to buy flowers like she did on March 19 in Manhattan, and she'll unlock a cohesive method of styling two vastly contrasting prints (stripes and checkerboard) while she's at it.
The Dawson's Creek star didn't have to venture that far from her usual outfit formulas—or paparazzi-filled route home—to deliver her Pattern Clashing 101 lesson. Holmes took in the early spring sun with a poplin stripe shirt unbuttoned to reveal a few choker necklaces, tucked into a pair of single-pleat gray jeans. Had she left the accessorizing at her pointed-toe white ballet flats, the outfit would have been a template for preppy spring layering. But then she toted her essentials in an out-of-stock Serapian checkerboard bag, and things got interesting.