Can a Man Wear a Hat Without Looking Like a Hipster?

This weekend, me and the family headed to the American Field Pop-Up Marketplace in Boston to check out a variety of companies making fashion and apparel right here in the good old US of A.

I was determined to buy something, but I would have never guessed it would end up being a hat.

You have to understand that I rarely wear a hat of any kind. Sure, I’ll throw on a baseball cap from time to time and winters here in New England means I wear a wool hat when I’m outside. But, besides that I’ve never thought of myself as a “hat guy.”

I got talking with the gang at Goorin Brothers Hat Shop and jokingly said, “I doubt you have anything that would fit this melon.”

He kindly grinned, looked at my head and picked a hat and put it on my head. It fit perfect.

It was one of those hats you see old time chaps wear on the golf course. I looked in the mirror and turned to my son to go find my wife and daughter since they wouldn’t believe I was wearing a hat.

While he went to find them, the owner picked out another one and put it on my head. Again, it fit perfect and I kind of liked the look of it.

“Wow!” is all I heard as I looked up and the women in my life were giving approving nods about how much they liked it.

Long story short, I bought the hat. I now own a fedora and I have no idea when or where I’ll actually wear it.

My New Hat

But, as an almost forty-year-old man I have to wonder if it is going to look like I’m trying to hard.

Sure, hipsters can pull off the look and if I was in Brooklyn or Portland no one would give me a second look.

Can I pull it off? It freaked me out just to take the photo and post to Instagram, but my daughter made me promise.

Help a guy out.

Ladies, what do you think of the look? Guys (especially those of you who wear hats), what is your advice.

I’m figuring it goes well with a suit or outside with an overcoat, but I have no idea.

Watching shows like Boardwalk Empire and Mad Men certainly makes me appreciate the days when men wore hats, but I’m not sure we are at that point again.

Hat lovers, let me know!

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