How to Be Stylish: Docker’s SVP Chief Creative Officer Tells Us

Having good taste and impeccable style doesn’t happen overnight. Sometimes, it takes learning from the best in the industry to truly perfect dressing like a fashion-forward, modern man. Welcome to our series, “How to Be Stylish,” where we pick the brains of some of the most respected figures in fashion for their ultimate style tips.

In the cult-classic comedy Seinfeld, we respected leading man Jerry for a multitude of  reasons: choosing a diner as a hangout that always conveniently had a table for four available, his penchant for selecting quirky friends, and his ability for talking about (let alone framing a whole show around) absolutely nothing. Jerry’s one flaw? His wardrobe. We mean, we’re talking about the guy who once donned a puffy shirt. And when he expressed his dislike for the Dockers commercial in one season of Seinfeld, we couldn’t help but roll our eyes. In reality, Dockers is the ultimate place for any style-conscious guy to pick up a versatile pair of chinos. In this installment of How to Be Stylish, we chat with Doug Conklyn, the brand’s SVP chief creative officer, about menswear must-haves and finding the perfect fit.

Doug Conklyn

Doug Conklyn | Source: Dockers

The Cheat Sheet: Can you tell me a little about yourself? How did you get to where you are now, career-wise?

Doug Conklyn: I pretty much just followed my passion for classic menswear, which began when I was pretty young. I started my “career” in high school, when I persuaded the owner of a prestigious men’s store to hire me for after school, weekends, and summers. Over the years, I held positions in retail, wholesale, sales, merchandising, and design in men’s, women’s, and children’s. But my love of menswear ultimately guided my career choices.

CS: How would you describe the Dockers guy?

DC: We have a lot of respect for our consumer. Internally, we refer to him as the “genuine good guy”. We think about him not so much in terms of age but more in terms of what drives and motivates him. From extensive research, we know that he is driven by intrinsic needs. Being true to himself and his family are key. He also places a high [emphasis] on being dressed appropriately for the occasions that matter and values classic, enduring style. And that’s where we come in. In other words, it’s a state of mind.

CS: Whether getting dressed yourself or leading the Dockers team, what’s the one style rule you always follow?

DC: For me it’s all about consistency. I’m inspired by classic menswear, so the devil is in the details. Depending on the day, I may have to dress up or dress down, the key to dressing appropriately for any given occasion is having the right accessories, especially shoes and belts. Classic menswear tends to be quite nuanced. I spend a lot of time with my team discussing the various subtleties of style and details and how best to bring them to life.

Dockers pants

Dockers pants | Source: Dockers

CS: What is the one thing that every stylish man should invest in?

DC: Great shoes. It’s the foundation of your wardrobe and worth the investment because when properly maintained, a great pair of shoes will last well over a decade.

CS: What are five things every modern man needs in his closet?

DC: A well-tailored navy blazer; a crisp white oxford-cloth shirt; a navy knit tie; well-made penny loafers or wingtips; and a pair of slim-tapered khakis from Dockers, of course.

Dockers pants

Dockers dress pants | Source: Dockers

CS: For some men, finding that perfect pair of khakis or chinos amounts to buying the first pair of pants they try on. What is some advice you can give Cheat Sheet readers for finding the perfect fit?

DC: For so long now, men have confused comfort with fit. In other words, if a pair of pants was roomy and comfortable, it was assumed that they fit. The good news is that you can get both fit and comfort with today’s stretch fabrics. If you really want to clean up your look, consider trying some of the new slimmer cuts of pants that are offered. We offer a wide range of fits at Dockers and we’ve seen a natural migration from the looser fits to the more tailored cuts. You don’t have to be a runway model to pull off the slimmer fits. So my best advice is to be open and experiment with a slimmer fit than you might typically wear.

CS: Many may remember Dockers for its highly contested commercial on Seinfeld. But as any fashion-forward reader knows, Dockers is more than that cameo. How do you and your team continue to grow the Dockers line to be a reliable brand for the modern man?

DC: The key is to focus on being both classic and relevant. We know that our guy respects classic style, but I’m always quick to remind people that classic doesn’t have to mean stodgy or boring. Through fit, fabric, pattern, color, and performance, we are able to continually evolve [timeless], iconic menswear in a way that keeps it fresh and relevant for our consumer. While it’s true that a certain segment of the population remembers us for those ads 20 years ago, a whole new generation knows us in quite a different way. Because we’ve been around for nearly 30 years, we’re a generational brand selling everyone from my father, to me, to my 16 year-old son.

CS: Where do you see Dockers five years from now?

DC: In five years, I see Dockers continuing to redefine the way men dress for casual occasions. Dockers began the business casual revolution 30 years ago. But today, business casual has evolved into everyday casual. Through our broad range of innovative fits, performance fabrics and extensive head-to-toe product offerings that span nearly every casual wearing occasion, I believe Dockers will once again revolutionize the way men get dressed around the world.

Follow Kelsey on Twitter @KMulvs