“. Gee, that pic makes him look like a reporter from the 40s, maybe it’s the hat.”
It’s an homage to Walter Winchell whose career inspired Matt Drudge. Look up a picture of Walter Winchell and you’ll see the hat.
I recall Matt Drudge and broadcaster George Putnam talking about this- George was a contemporary of Walter Winchell and recognized both the style of Drudge’s reporting and the look that Matt was affecting.
I love that he does that. I like that old time reporter look and Drudge does live up to a real investigative reporter. He’s fabulous.