Lee Pitts: Ask The StyleMaster | TSLN.com

Lee Pitts: Ask The StyleMaster

It’s been awhile (30 years) since I, the god of good taste, answered your many questions regarding what’s in style. It’s quite natural that you’d seek guidance from such a fashion forward expert as myself. By the way, I learned that term, “fashion forward,” the last time I was stuck in a “semi-private” room in the hospital and there were three beds, five generations of family belonging to one of the other inmates, and ONLY ONE REMOTE CONTROL! I was forced to watch a marathon of Project Runway reruns. I told the Doc if he didn’t let me go home I was going to kill myself because I couldn’t take one one more minute of Iron Chef or the Property Brothers.

While my good friends may NOT be surprised to learn that I’m still wearing the same Pendleton wool shirts I was wearing three decades ago, there have been many changes in the fashion world since last time we visited. So, once again its time to “Ask The StyleMaster.”

Dear StyleMaster, Are lace-up cowboy boots in fashion or not? Signed, Conflicted.

Dear Conflicted, I’m glad you asked because this is something I have strong feelings about. While it’s okay for a cowboy to wear lace-ups while he’s fixing fence, washing dishes, or feeding cows, a real cowboy never wears lace-ups while riding a horse. I know from personal experience that as you’re being drug over rocks, tumbleweeds and cactus because one of your lace ups is stuck in the stirrup of a runaway horse, you don’t really have time to untie your shoes.

Yo, what’s up? I was trippin’ on a rodeo on my iPhone and saw one of the saddle bronc dudes was wearing a necktie. What’s up with that? It makes as much sense as surfers wearing ties. Signed, Strangled in Santa Monica

Dear Strangled, I feel your pain. While it’s true that many years ago some cowboys actually wore neckties to work and at rodeos instead of wild rags, it is NOT a fashion trend we need to revisit or encourage. After all, we are cowboys, not accountants. What’s next, Ralph Lauren sheets in the bunkhouse?

Dear Fashionista Friend, Do the old rules still apply as to when to wear your felt and when to switch to a straw? Joe Stetson

Dear Joe, are you any relation to John B.? If so, do you have any free samples? I’m size 7 1/4.

Anyway, back to your question. Have you seen the prices for felt hats lately? I don’t care what month it is you should never wear a $400 hat to work if it’s going to get dusty, sweaty, squirted with blood or manure. Or stolen. As Lyle Lovett says, “You can have my girl but don’t touch my hat.”

Of far more importance than when to wear a hat is the width of its brim. As a general rule, the uglier the face, the bigger the brim in order to hide the face. I myself wear a Mexican sombrero big enough to shade me and my ugly horse.

Dear StyleMaster, I notice that names on the back of cowboy belts are out of fashion while bling is in. Will names ever come back on the back of belts? If not, do you know any leatherworker who wants to buy a thousand dollars worth of alphabet stamps? Signed, Belt Maker in Billings

Dear Belted, The first thing I think when I see a cowboy wearing lots of bling is the guy is a little light in the loafers. Save those letter stamps because names on belts will definitely come back because there was a darn good reason we put names on the back of cowboy belts.

Being a cowboy means you ride a lot of horses, not all of them broke. This means a cowboy will invariably become a sky pilot, being bucked to the moon and back. Nine times out of ten he’ll land on a big pile of rocks and his body will be misshapen, blood oozing from every orifice, arms and legs snapped in two, and nose, lips and ears found in locations on the face where they shouldn’t be. In many cases the cowboy is unrecognizable. So you roll him over, look at the back of his belt and proclaim, “Yup, I thought so. It’s Roy.”

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