Katie Holmes Aces High-Low Style with Her Madewell Bucket Tote

First off, the bucket tote is oversized, one of our favorite handbag trends because it’s actually useful. (No shade to Taylor Swift’s little date night bag, but we prefer a purse that fits our wallet, phone and even a water bottle.) Capacious as well as cute, this bag turned up on Holmes’s shoulder when she attended the U.S. Open, where she wore it with jeans and a Miu Miu Argyle sweater ($2,050) that she tied around her shoulders when the match heated up. It’s a signature Holmes look. As she told British Vogue, “My personal style is pretty classic. I like taking risks and having fun with fashion but I tend to gravitate towards simple design.”

A few weeks later, Holmes was out and about in New York City, running errands wearing sweatpants, a hoodie and Adidas Samba sneakers ($100), which PureWow’s fashion editor deems one of fall’s top shoe trends. And along with a bouquet of fresh flowers, a bag of retail purchases and a to-go bowl, what was Holmes carrying? Her Madewell Essential Tote, of course—in a chocolate raisin colorway that’s available for pre-order now, while colors indigo, true black and warm cinnamon (that last is our favorite for its 1970s-throwback grooviness) are in stock now.