Four Inane Questions with Shepherd’s Co-Founder Nathan Price

Courtesy of Nathan Price

Call him what you will—clothier, haberdasher, dresser of dudes—but Nathan Price is determined to get guys gussied up. Price is the co-founder and Chief Product Officer of Shepherd’s—a menswear brand founded in Kansas City. “Shepherd’s makes tailored garments for men, using only the highest-quality materials,” says Price. “And they’re made in European workshops that we’re proud to partner with.” 

Their downtown showroom has become an oasis of sorts for fashion-centric/fashion-forward men—and the occasional unfashionable bro in search of a new look. It’s also become a low-key stomping ground for athletes, local celebs, and musicians to pick out made-to-measure heirloom apparel.

We caught up with Price—by appointment only, dammit!—to zing him with our zany questionnaire. We also got fitted for a new, luxe Italian tuxedo. We’ll be putting a down payment on that once our tax refund surfaces. Bless. 

The Pitch: Admit it, does anyone look good in an ascot? 

Nathan Price: While it may be possible for an ascot to look good on a guy—by choosing the right colors and pattern—I would argue that in today’s context, it looks more like a costume. 

When done right, an ascot is a tasteful accessory to an outfit that leans into a preppy aesthetic. If it’s worn under a white shirt in a shade of blue, red, or yellow, and paired with a classic blazer with metal buttons, it can look sharp. 

However, ascots haven’t been worn with any regularity since the early twentieth century. Plus, menswear has continued to become more casual. Wearing an ascot today leads to the wearer looking more like an advertisement from the 1920s, than a well-dressed man of today. 

What cereal could you eat every day for the rest of your life?

Rice Krispies. I have many childhood memories of pouring a bowl at the breakfast table next to my grandfather during summertime visits to Kentucky. I haven’t had them in years and they probably don’t taste great, but I’d always think of playing catch in the yard, shooting marbles, or going to baseball games with him. 

My two-year-old son has some from Magic Spoon that are pretty good, too. Maybe that’ll be his answer in twenty years. 

Courtesy of Nathan Price

What’s a pattern no self-respecting man should ever wear?

I think that most patterns can work in the right context, but I am not a fan of overly zany paisleys. If the entire tie or pocket square is one large swirling paisley pattern, it looks overpowering. This type of pattern can look particularly off-putting in silk, especially really cheap, shiny silk, found at most department stores. The entire point of a tie is to draw the eye to the wearer’s face, and a wild paisley tie will often deter that. 

I do love small micro-paisley patterns, where a tie has 30-40 micro-printed paisley designs on it. This is a nice substitute for a geometric print or a small floral print tie. Also, I certainly would not recommend gentlemen wear paisley-patterned shirts. Don’t get me started on those. 

If you were a famous painter, which famous painter would you be? 

It would have to be Michelangelo. There are few artists with the skillset that he possessed. 

When I was in Milan a few summers ago, I was able to see one of his lesser-known works, the Rondanini Pieta, which he sculpted in the final years of his life. I look forward to visiting Rome one day on a future trip to see some of his more iconic pieces, like the ceiling of the Sistine Chapel, and the Pieta. 

While it is one thing to marvel at his work, I also admire how his Catholic faith continued to deepen as he aged, and how his struggle with mortality came to life in his work. 

Bonus 5th Questions: If you had to give a TED Talk on the fly, what subject (or subject matter) could you pontificate on for 30+ minutes with ease?

In the world of tailoring, I could riff on topics like fit, wardrobe building, or what makes a quality garment. I spent a week in Huddersfield, England a couple of summers ago to learn how wool is made. I certainly could talk about that—especially if you need help falling asleep! 

I also love American history, so discussing topics like the Revolutionary War, World War II, or the space race could easily take me past the 30-minute mark.