Despite his wife’s protests and his friends’ many jokes, the writer Isaac Fitzgerald spent three days in London shopping for a hat straight out of Peaky Blinders. Here’s what it taught him ...

Wear it on busy, errand-running days. On a Sunday afternoon, a driving cap or newsboy cap will keep you from looking like a gym rat, while still checking all of the boxes that your go-to baseball ...

The ivy hat, sometimes called the newsboy cap, is popular because it’s versatile. McDonald notes that the wearer of an ivy cap can add swagger by tilting it left or right or even turning it ...

Let me fill you in: There were newsboy caps on the Chanel, Anna Sui, Prada, and Celine runways. Then, pillbox hats were spotted at Altuzarra, Alberta Ferretti, and Emporio Armani.

The newsboy style may have wedge-shaped panels, sometimes with a more curved brim and a looser fit, while the flat one boasts a sleeker design, with fewer panels and typically a distinctly flat brim.