A confession: When I turned 40 last year, I felt insecure about how I looked: my clothes, my hair, my skin. I wasn't concerned about looking old—okay, maybe a little—but instead looking complacent. Like I stopped caring (even though, paradoxically, I try very hard to look like I don't care, even though I care very much). I didn't buy a closet full of new clothes, change my hair, or alter my skincare routine. I sought inspiration. I created a moodboard of famous people when they turned the big four-o. I wanted to see how they dressed and looked. I started sharing the moodboard with friends staring down 40, and then decided, what the hell, why not share it with Esquire readers.
Here it is: an incomplete collection of notable men at the precise age of forty. I hope you enjoy it, whatever age you might be.
Forty can be a tough age, even today, especially today. But these guys—from Ernest Hemingway to Jay-Z—made it look effortless, cool, and aspirational.
