Lessons from “A Man of Style”


I few weeks ago I shared in a blog post a photo of a very unique gentleman I saw at the Round Top (TX) Antiques Fair. In case you didn’t see it, here it is again:

two gentlemen at Roundtop

I’m sure you can see why he caught my eye. Well, fast-forward to now, where I just serendipitously found out more about him. He’s got a story (as you might well imagine.)

The story, entitled “Man of Style”, appeared in Texas Monthly and shares a little peek into his interesting life. The ‘he’ is 75-year-old Derrill Osborn, a former men’s fashion director at Neiman Marcus in Dallas. (Starts to make a little sense already, doesn’t it?) He lives in a 1,000 square foot apartment decorated primarily in reds and greens. He says,

“My mother was a pistol. Her name was Flossy Faye,
and my grandmother, Lily Mae.
I never saw my grandmother wearing
anything other than red, and my
grandfather was never without
a prairie flower in his lapel.”

Photo: Wynn Myers

With those kinds of genes, it’s no wonder he embraced the world of fashion and style. He’s been featured in GQ, Esquire,and Women’s Wear Daily, and has been photographed many times by legendary New York Times fashion photographer Bill Cunningham.

My second serendipitous encounter came when I was recently flipping through one of my favorite fashion inspiration books: Advanced Style Older & Wiser, by blogger and photographer Ari Seth Cohen. Low and behold, there he was again. It’s clear he’s been admired for his unique style for quite some time.


You can see many more photos of his fabulous apartment, read about his collection of art, canes and first editions, and more about his history in the Texas Monthly story, but I wanted to share one more quote from him about his time in the men’s fashion industry:

“It was a wonderful time in menswear. Men had
clothes for every occasion—black tie, a host of suits,
sport coats, a wardrobe for spring and fall.
Fashion was seasonal, which made it exciting.
You never knew what was coming.
But I never foresaw what would happen
in fashion today. I was blindsided,
and I miss what it used to be.”

So what are the lessons to be learned from this “Man of Style”?

Here are a few of my take-aways:

* The times will change, sometimes to our liking and sometimes not. If you know your “style personality” (which translates into the style words you use to describe your style), you will be able to flow with the times and still remain true to yourself.

* If you truly know your personal style personality, it will easily translate throughout your environment. When you look at the pictures of Mr. Osborn’s home, you can see ‘him’ there. His personal style of dress and his home are in agreement. I realize that you may not live alone and have to adapt to others in your household. In general though, when someone walks into your home they will be able to detect “you” there. If they can’t, you may want to make some changes either in your living environment in part, or maybe in reevaluating whether your style words have evolved into something new.

* Fashion can be fun! Even if you mostly dress in an elegant and refined manner, there should be an element of fun when you dress for the day. It might be something that’s known only to you, perhaps in an undergarment. I think of it like our “inner fashion child” – she wants to come out and play, perhaps even more so as we get older and feel less constrained by outside forces.

Mr Osborn clearly has his style well-defined and is a good lesson in what results when you know your style well. He must enjoy getting dressed in the morning, knowing he’s going to delight those who see him. Which begs the question – of myself and of you – do you find delight in getting dressed in the morning? If not, maybe some changes are in order.

I’d love to hear of any other lessons you might have learned from this “Man of Style”.  Please do tell. If you’d like to follow Derrill Osborn, here’s his Instagram feed: @derrillosborn

Thank for reading – stay stylish!


Adena DiTonno

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