Founder profile: Chris Cottrell

Never doubt the mysterious power that resides in well made clothes, for they make the humble handsome, the slumped stand straight, and the impecunious feel like a million bucks.

Clothes also have the power — when united with enterprise — to bring together men bound by a common enthusiasm. Such is the case with Shepherd’s, whose fab four founders may have vastly different backgrounds, but who joined forces to preserve and promote tailored clothing precisely at the moment in time when such a team was needed.

Friend and colleague Christian Chensvold, menswear historian and author of The Philosophy of Style, continues his series of Shepherd’s profiles with Chris Cottrell, the business brains of the team, whose previous accolades include a Bronze Star for his military service as an intelligence officer with Special Operations Command in Iraq.

CC: You have two master’s degrees, one from Georgetown and one from Harvard, and yet here you are in a menswear startup.

CC: Yeah, I guess it’s off the typical path, isn’t it? I’ve always enjoyed having an idea and then building it and see it come to life, especially when it’s with a great team. The traditional, more secure, and less-consuming career paths just never seemed as enjoyable to me, and I feel very blessed to be doing something that I love.

Shepherd’s is also more than just another clothing business; we’re building a brand and voice in the menswear space. That means we have to really think about what we want to say and how to do that.

CC: And what about the clothing side of it?

CC: I think growing up I was conscious of not knowing how to dress well or what that even meant. I think my generation never had those kinds of rules expressed to us, so we’ve had to figure it out on our own. That’s certainly a process and the deeper is how does a man strive to be better—in a way it’s asking how to seek honor—in a society based on equality. In the end it’s about striving to be the best version of yourself but that also requires you saying, at least to yourself, “I want to be better than average.”

CC: Did any films have a special influence on you?

CC: I grew up watching the classics, like Gregory Peck in Roman Holiday and Jimmy Stewart in It’s a Wonderful Life, which gave me a bit of yearning for that classic, dignified, and simple men’s tailoring.

The other theme was the old Westerns, which I loved as a kid and still often watch, like True Grit and the old Lone Ranger series. The west had a very functional uniform that I still love and, being from Arizona, I’m pretty often pairing a pair of cowboy boots with one of our blazers.

CC: Some dressers pare things down to a uniform, while others begin in a uniform and then expand their horizons. Which are you?

CC: I lean more toward the uniform side. If I find a staple that I really like, like underwear or the perfect dress shirt, I’ll just buy several of them, so I don’t have to think about it. I want to solve the problem once instead of feeling like I’m solving it every day. It’s important that each guy is doing—and wearing—what is authentic to them, and that’s certainly authentic to me. It would feel a bit like a costume if I was wearing some of what you see at, you know, Pitti Uomo or something. If someone passed me on the street I think (I hope!) they’d think I’m well-dressed but what I wear doesn’t shout that I’m into menswear.

CC: But you’re surely opening men’s eyes to this world now.

CC: Certainly, especially around fit. When a client comes in and says, “I’ve never had anything that actually fits before,” it is a joy to give them something that was actually made for them. They can feel it right away and you can almost see them finally relax because they feel comfortable.

CC: What is your vision for the company, and what you’re bringing personally to make it successful, and helping uphold time-tested standards?

CC: Yeah, everything—every business, garment, and person—has its context. Our context is not one in which every man needs to wear a suit and tie to the office five days per week. I think that’s out of touch.

CC: Absurdly so.

CC: Right. Maybe in twenty years that will be the context, but it isn’t now. So, when Shepherd’s says a man should dress well, that doesn’t mean only suits and ties, although that’s often part of it.

For us, being well-dressed means wearing something that is intentional, meaning some thought was put into it; appropriate, meaning it is being worn in the right context; authentic, meaning it reflects who the man is or is aiming to be; and it is elevating, meaning that it lifts the spirit and self-perception of both the wearer and those around him.

So yeah, that’s intentional, appropriate, authentic, and elevating. We want to move guys a level above what they’d normally wear and that’s going to be very different for each guy. Tailored clothing has a real chance for a comeback if it’s comfortable and sensitive to the times and is not trying to impose a costume.

CC: Some men are businessmen, and some are artists, and they can both be interested in tailored clothing.

CC: Exactly, so long as it’s authentic to the guy. It would be costume for me to be in a royal blue windowpane suit, and for other guys it would be a costume to be in jeans and cowboy boots. Making things that fit the man—both physically and metaphysically—is important to us.