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THE SUNDAY EDIT VOL. 96 | Cowboy Hats Habits Style

Cowboy Hats Habits Style

We have discussed the Western style before. This edit focuses on a vital piece of that style, the cowboy hat.


Words By: Arcy Hawks

Recently, two style gurus have brought this piece into the spotlight in high fashion. Pharrell Williams’s collection for men’s Louis Vuitton heavily featured the cowboy hat and Beyonce’s debut into the Country Western music genre. This has created an entirely new set of hat connoisseurs. This isn’t the first time or anything new. If you step outside of Habits you will most likely run into a hat store. With four hat companies in our small town, you won’t come up short if you are in the market for a topper.  Now, as I was told once by the first person to bring that style into the mainstream, Nick Fouquet, you only need confidence to look good in a hat. And from where I was standing, he had that in spades.

As we discussed this Sunday edit we always want to circle back to Habits Style.  How we incorporate our edits into our style, vision, and philosophy.  This edit was perfect for this because we wanted to show you how the Cowboy Hat in itself is Habits Style.  In or version, it’s timeless, it transcends trendiness, it is made by a single person’s hand, and it is made to last.

Growing up in El Paso, Texas I knew quite a few cowboys.  Not in the ranch hand sense but the rodeo sense, the horse trainers, and groomers who worked in the racehorse industry.  Each had a very distinct way of wearing their hats and took pride in them.  You didn’t wear a felt hat in the summer unless it was a special occasion. It was never overly done or had any kinda of embellishment.  Maybe a handmade horsehair band but that was it.  No pins, feathers, or god forbid playing cards. They were shaped to their liking and you never, ever, set a cowboy hat flat on a bed.

We were inspired by local hat maker Christy Sing. Her authentic voice and commitment to her craft are inspiring. Christy’s studio is bustling with activity, and her passion for a real representation of this iconic piece of Americana is infectious. We played with some of our favorite shapes and how Habits styles them. We chose pieces that reflect our modern fashion sense along with traditional Western flair. 

If you choose to get yourself a cowboy hat, choose wisely. Choose real and choose the best you can afford. You might not wear it all the time, or you just might want to get on this trend,  I guarantee that if you go with a true, meaningful, and well-made one, you will cherish it as an art piece long after the trendiness wears off. Because real, future vintage, and well-made are Habits Style.


Words By: Milli Dawson

Growing up in Cheyenne, our biggest event of the year was “Cheyenne Frontier Days” which is also known as “The Daddy of em’ All” or “The World’s Largest Outdoor Rodeo”. The entire town comes alive, hotels and bars are full and a new crowd comes to visit. I grew up on a ranch and my father is a Large Animal Veterinarian so this world of cowboys and rodeos was all I knew as normal. The one part that my dad and I always laughed at was the influx of “cowboys” and their big, ol’ hats in our town.  My father, a very humble cowboy, has never been seen in a cowboy hat. He is more of a baseball cap kind of guy, he doesn’t like the attention.

Many hats have been worn in my family, as my generation is the 5th generation of cattle ranchers. My Great Great Great Grandfather Milton Dobson founded our family ranch in Kansas in 1901. He is seen pridefully wearing his Prairie-style hat in this image taken in 1905. There is something very special about the “Cowboy Hat”. It’s a “sign of the times”, many different times.

I have conflicted feelings about Cowboy hats today as the folks who are mostly wearing them in current times are people who don’t quite understand what it means to be a cowboy. There is no dirt on their hands, muck on their boots, or understanding of the world they are trying to represent by wearing their silly hat with matches in it. I recently had a laugh with Arcy when Pharrell said that he brought “real cowboys” to his show. The real cowboys I know, would never consider going to a fashion show to miss a day with their cattle. Maybe the cowboy hat is still a “sign of the times” but not like it used to be. Just in a way that as a society, we are all trying to be something that we are not. Authenticity is rare.

With all of that being said, wear a cowboy hat. Have fun with it, because at the end of the day, it’s just a hat. Like anything that Habits stands for, find the best hat. Go to Christy Sing, and have her make you an old-school, well-crafted, beautiful hat that will last through your entire life.     

CS:    Thank you, Arcy!  So grateful, flattered and excited!

AH:    Why a Hatmaker?

CS:    It was a call from God in the middle of a normal week.  Not so much audible, but a call, nonetheless.  I listened and found an internship (6 months later), and Sing Hat Co was born.

AH:    What brought you to Jackson?

CS:    Again, a call from God.  An interruption in my normal, happy life.  I came two weeks later.  That was 21 years ago.

AH:   What is the most rewarding part about your chosen path?

CS:   Working with my hands is pretty special and rewarding.  I’ve spent most of my time hatmaking working on the craft.  Trying to be better all the time.  I’ve chosen that path, instead of growing the brand, per se.

AH:   I love  that your voice pushes against  this fast fashion, jump on the bandwagon trend, and get it done quickly society. What would you say is the biggest motivator for this voice and why is it important to you?

CS:    I love old things.  Reusing/repurposing them.   I wear a lot of vintage clothing and jewelry.  I’ve seen what a hat (and clothing) looks like when fashioned quickly.   I prefer to do things well, not in a hurry.  I try to purchase and wear things that are made with this ethos, as well.

AH:    I grew up in Texas and have lived the better part of my life in Wyoming, I have seen my fair share of “dudes”.  Do you think this dilutes any authenticity or does it really matter?

CS:    I’d love to say no.  And if you’re not a “dude”, you can generally see authenticity, but lines might be getting blurry for the untrained eye. 

AH:    Last Question for us fashiony ladies.  What’s your favorite piece of clothing and do you have a daily uniform?

CS:    If I have to choose one item, it’s well-fitting jeans. I’ve always worn a cotton snap shirt until it’s threadbare.  The kind my granddaddy and uncles would wear.  A friend coined the term “feedstore grandpa”.  That checks out.


For more articles and takes on History of the Cowboy Aesthetic and Modern ways to style.






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