Katie Holmes Relaxes a Designer Dress With Her Affordable Madewell Bag and Fisherman Sandals

On a summer Friday, I'm all about an easy work outfit recipe I can assemble in five minutes or less: breezy layers, comfortable sandals, and maybe a hint of menswear if I really want to get down to business (but in a casual way). Katie Holmes joined my wavelength a full 24 hours early this Thursday, juxtaposing a designer dress with her affordable Madewell tote bag, chunky fisherman sandals, and an oversize button-down shirt.

Holmes effortlessly balanced on the high-low tightrope power-walking around New York City while chatting on the phone. These, loyal fans know, are the times that Holmes usually cooks up her best nonchalant street style. She delivered once again on June 20, beginning with the base of a colorblock sundress by Ukrainian designer Bevza. She added a blue and white striped shirt on top, unbuttoned all the way to beat the week's heatwave—and show how she subtly played on the dress's seaside-toned palette.

Then came her accessories, starting with her Madewell bucket bag. The roomy, under-$200 leather tote first appeared in her wardrobe last fall alongside a pair of Adidas Sambas. It flew off of shelves shortly afterward, owing partially to its five-star ratings and partially to Holmes's stamp of approval. (Don't worry: It's back in stock.) She carries it just as often as its cousin: a black, everyday tote by Mansur Gavriel.

Meanwhile, her as-yet-unidentified woven leather sandals marked a completely new wardrobe addition. So far, Holmes has spent spring and summer either reviving the wedge sandal trend with a pair from her A.P.C. collection or dressing up her Birkenstocks. Fisherman sandals have runway endorsements from The Row to Gabriela Hearst to Alaïa, so they were overdue for a cameo in Holmes's closet.

At the same time that Holmes was dressing down her work dress, she was also joining an emerging celebrity street style moment. Oversize, pajama-like tops are the relaxed summer shirt trend A-listers can't stop wearing this week, from Selena Gomez (with black pants and Zara sandal heels) to Jennifer Lawrence (with Mary Janes and a slip skirt). Even Jennifer Lopez, traveling solo in Italy while wearing a matching set and Dior basket bag, has worked an oversize shirt into her dolce vita wardrobe.

Considering that Katie Holmes will often squeeze three chic outfit changes into 24 hours, this may not be the last look she parades today. Still, it's the one I'll have in mind when I'm assembling my own summer Friday outfit tomorrow morning.