It's been a very long time since I thought a cowboy shirt was a cool thing to wear. I remember when I was about 11 years old I had a denim one myself--it was from The Gap when The Gap still sold Levi's (remember that?). I wore it for a year or two, and I remember the moment when I saw it hanging in my closet and nearly shuddered with repulsion--it just suddenly looked so wrong. Who was I trying to be--Daisy Duke?

For more than 20 years I didn't give cowboy shirts a thought. Then, recently, I was touring the newly renovated house of my friend the photographer Charles Thompson, and I wandered into his closet. Because I was used to seeing him out at night in impeccable custom tailoring, I was shocked to see a row of denim cowboy shirts. They were lovingly worn in, with no extra details like embroidery or contrast piping, and they were all made by Wrangler. "They're all I ever wear in the daytime," he proudly confessed. I was confused. How could a guy who is so well dressed rely on cowboy shirts as the main staple in his wardrobe?

After that day, as if by karma, the cowboy shirt was practically seeking me out, asking me to reconsider. Everywhere I looked--on the streets, on my friends, in vintage pics online--cowboy shirts were popping up, looking not so bad. I think it was a candid photograph of Robert Redford looking rugged yet astonishingly handsome in a red cotton cowboy shirt that convinced me to turn this sartorial corner. I'm not trying to say that there is a cowboy trend going on; it's just that--you know when you learn a new vocabulary word, you suddenly notice it everywhere? It's like that. And now when I see a guy wearing a cowboy shirt, he seems to be saying, "Don't mess with me"--and, sometimes, "Come over here and mess with me." I like both messages. I might even go so far as to say that these shirts are cool.

This picture of Robert Redford in his red cowboy shirt stopped me dead in my tracks. I've been obsessing over it for a while now and, in truth, created this week's blog solely as an excuse to include it. (Corbis)

Photographer Charles Thompson (with his daughter, Anastasia) in his daily uniform of a Wrangler shirt and jeans. Brooklyn Heights, NYC, May 2007.

I have to confess that I cropped this photo because this man was wearing some very unfortunate pants (WAY too tight for a man)--but his top half looks great! NYC, July 2007.

My stepfather and great grandfather on the beach in linen cowboy shirts. It's the WASP interpretation of a Western look. Quogue, NY, 1979.

This guy took his cowboy look pretty seriously. I like it, though. Brooklyn, NY, August 2007.

This is undeniably the coolest one could ever hope to look in such literal cowboy gear. Dennis Hopper and Henry Fonda on the set of Easy Rider, 1971. (George Stroud/Getty Images)

I couldn't resist this picture of Tom's Shoes founder Blake Mycoskie, even though he was on my blog last week. He's hot. (Alexa Elsberry)

Ronald Reagan in a plaid cowboy shirt at his ranch in California, 1978. (Getty Images)

I saw this guy in his plaid cowboy shirt at a cafe in London, and I just got a vibe that he wasn't going to let me take his picture, so I snuck one. Tom's Cafe, London, June 2007.

Folk singer Ray LaMontagne wears a white cowboy shirt during a concert in New York City, 2005. (Getty Images)

Boys dressed in cowboy outfits at the annual Helldorado festival in Arizona, 1950. It seems to me that most men wearing cowboy shirts are in some part reminiscing about their childhood cowboy fantasies. (Getty Images)

This guy is kind of half preppy (plaid shirt, boat shoes), half street (messenger bag, rolled jeans, graffiti). I like his undefinability. Brooklyn, NY, August 2007.

Don't you think this man looks like a character actor from the movies? Regardless, he looks good in his denim shirt, glasses, and slightly cynical expression. NYC, July 2007.

I can't resist including another one of Robert Redford. For me, he did the cowboy look best. (Corbis)