How to Wear a Newsboy Hat. You don't have to be a "news boy" to wear a newsboy hat; this traditional style of cap has morphed into a kind of headgear for everyone, from the older gentleman to the young clubber. Wearing one is not difficult, but knowing about newsboy hat styles is a little more involved, as the genre of hat expands into the marketplace.
Know the difference between a "newsboy" hat and a news man's hat. The latter is the fedora, with press card tucked neatly into the brim, that reporters wear while out in the field. The news boy's hat, on the other hand, is the front-brimmed cap worn by young newspaper vendors back in jolly old England, before all newspapers were put into neat coin-operated kiosks. Trying to put a press card into a newsboy's cap would be improper and difficult.
Wear the newsboy's hat in relatively good weather. The English had other headgear to wear with their Macintosh for rainy days, and so do Americans. Choose a raincoat or weatherproof hood for when it's really coming down.
For knit newsboy style caps, wear the hat with the brim unattached to the cap. This style shows a profile of a head with a larger rounded cap on top, and this is the way young hipsters generally wear their newsboy style hats while out and about.
Wear the old-school fine knit newsboy style hats with the brim snapped to the top of the cap. This gives the cap more of a "captain's hat" look, and is preferred by older gentlemen in tweeds.
Wear the newsboy cap properly up on your head to show your eyes. Wearing the newsboy's cap slouched down over your face is the almost exclusive habit of old-world gangsters, ne'er-do-wells, and devilish manifestations in old Faust legends. A good citizen wears his/her hat comfortably pushed back to keep face to face meetings properly accessible.