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Dockers creative director Doug Conklyn.

When it comes to all– American style authenticity, Doug Conklyn is a proverbial poster boy. On the verge of turning 50, the east coast-raised, California convert, who once worked for Ralph Lauren, prides himself on dapper dressing and skateboarding to work. For the past five years, Conklyn has been the creative director of Dockers – the 30-year-old casual men's-wear brand owned by Levi's – and his mission is to keep the romance of a simple pair of chinos alive by not only reminding us of their cross-generational relevance, but by making us understand why they've earned "classic staple" status in the wardrobes of modern men the world over. I spoke with Conklyn from San Francisco recently about Dockers' 30th anniversary, the enduring appeal of the brand and, as he calls it, fashion's "casual continuum."

What has been your biggest challenge with the Dockers brand?

The thing that's requiring a lot of effort – something we're really focused on – is to help people understand how Dockers has evolved over the last 30 years. There are still a lot of people walking around with a decade-old perception of the brand in terms of what we make, who we make it for and how the product fits. After 30 years of business, we're serving multiple generations. I always like using the example of my 76-year-old father who wears Dockers, I wear Dockers, and my 16-year-old son wears Dockers. The three of us wear it in different ways, with different fits and different styles. It's fun for me because we make so much product and we're able to make it for so many different people.

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Is that the brand's biggest story? That it has this cross-generational appeal?

That's definitely an appeal of the brand, but I think the biggest story is that we're a brand that ushered in the world of business casual. Since I've been at Dockers, the biggest growth in our business is coming from the much more casual part of our collections. As I've seen where we're trending, there's something I call the "casual continuum." When we started 30 years ago, a pair of sharply creased khaki pants and a navy blazer was considered casual relative to the suit. Today, that's almost on the dressier side of life because people are wearing jeans to work, or even shorts, depending on where they are. So the whole dress code has continued to shift much more casual. The fastest-growing part of our business has been in the side-pocket, jean-cut style, broken-in chinos.

To what do you attribute this desire to be relaxed when it comes to dressing?

I think it's a couple things. Once the dam broke, once the suit was knocked off its place as being the appropriate work uniform, it opened the flood gates for a more casual way of dressing. And once people start dressing more casually, it's hard to go back. I love tailored clothing, neckwear and fine dress shoes, but I'm finding myself with less and less occasion to really dress up. I think the world has changed. It's become more casual. But one of the reasons it has picked up such a momentum in the past several years is this term that everyone's throwing around: "athleisure." I think the world is obsessed with comfort and people have a higher expectation of being comfortable today than ever before.

Some guys do this casual thing a lot better than others. What's your advice to a guy who doesn't have the confidence to start mixing it up?

I would never confuse being casual with lacking style. Part of dressing appropriately is dressing with care. For me the foundation is fit, and it's important to really pay attention not only to the way your pants fit, but to the relationship of all the other pieces, too. If you're wearing a slim pair of trousers, it's probably a good idea to wear a shirt that has a similar sort of cut. Whether you're a guy who's going to step out with bright colours, or prints, or plaids – that's an individual choice. But at a bare minimum, making sure your clothes fit appropriately, and then having the right accessories, is important. And that goes down to the watch. In a world where people tell time with their phones, I still think they are key accessories that set you apart.

You've certainly set the tone for a style sensibility that resonates with all kinds of men. It's not about age so much as it is about a spirit of dressing.

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Yeah it's true. I'm going to turn 50 in June and today I'm wearing my skinny khakis and a pair of Vans high-tops and my own top. It's pretty much my uniform: khakis and an untucked white Oxford shirt. I don't feel like I dress my chronological age – I dress how I'm feeling and I think a lot of men are that way. So we design in a spirit of providing product that makes men of any age look and feel great. I've always thought khakis were cool – it's such a versatile garment. It's the cornerstone of any man's wardrobe. It has a beautiful sort of authentic heritage. The khaki to me can go as casual as a pair of jeans, if you wear it with a pair of sneakers and a T-shirt. But just by changing a few accessories, putting on a nice lace-up shoe and a blazer, it has this amazing bandwidth to go from one exunitreme to the other. Today, guys need that kind of versatility in their lives.

Do you still skateboard?

I do. I got married about a year and a half ago, and we bought a house north of the city. But when I had the apartment a couple blocks away, I would skateboard to work every day. I still skateboard a ton and try to act like I'm a teenager from time to time.

Now that you're about to turn 50, what words of advice do you give to other guys approaching that point in life, when they start to worry a little bit about what they've got to do to hang on to that youthful spirit?

Just don't give up. It's never too late. It doesn't matter if you're in great shape or not in great shape. Take care of your appearance – and I'm not talking about it in a vain way. We talked to guys around the world and they all share that same sense of wanting to present themselves genuinely and authentically… It's a fun time in terms of what's available out there. And whether you're turning 50 or 60 or 30, I think taking that personal pride and taking care of yourself pays off. When you look good, you feel good. I've often thought you can't change your life, but you can always change your clothes. To me, there's something really powerful in that.

You dress with a lot of panache and imagination. What's the secret?

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I had a lot of great role models in my life. When I worked for Ralph Lauren I used to see Ralph regularly. It was like everyday was Halloween, and I mean that in the best possible way. One day he'd be dressed like a military guy, the next day a Formula One race-car driver, the next day an East Coast prepster, the next day a bespoke Saville Row guy, or a cowboy… I always refer to my own closet as sort of a theme park of clothing because, depending on how I feel on any given day, I might mix a military influence, or a Western influence, or work wear. But right now what I'm most excited about is I've mixed that sort of East Coast preppy thing I was raised on, with this California surf-skate kind of thing, so it feels more relaxed. I feel like my two worlds have finally merged into one sensibility.

This interview has been condensed and edited.

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