How to Be Stylish: Dwight Fenton, Chief Creative Officer of Bonobos

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.

As any shopping savvy guy knows, buying the perfect pants online is not easy. After days of carefully tracking the parcel’s route, you may find yourself left unsatisfied with the fit. But when you have a demanding work schedule and a hectic social life to tend to, finding the time to scour the streets (or the corridors of your nearest mall) for those trousers with a perfect hemline and waist isn’t easy. Enter Bonobos, the affordable menswear brand that is committed to make your shopping experience easy.

Whether you make an appointment at one of the brand’s 10 plus guide shops, where you can receive guidance from one of the store’s attendants, or shop around on their website, which Bonobos happens to be the largest clothing brand built on the web, consider this company a one-stop-shop (or site) for fashionable, fitted clothes. And who do you have to thank for your new threads? Dwight Fenton, Bonobos’s current Chief Creative Officer. With experience from design gigs at Old Navy and J.Crew, Fenton oversees the design of all menswear categories including suits, woven shirts, denim, knits, sweaters, and outerwear and manages the full Bonobos design team. And, for your sartorial enjoyment, we sat down with Fenton to talk fashion, the future of e-shopping, and secrets to finding the perfect fit.

Dwight Fenton

Dwight Fenton | Bonobos/Nicholas Prakas

The Cheat Sheet: Tell us a little about yourself. Where were you, career-wise, before Bonobos?

Dwight Fenton: I actually started as a product developer and merchandiser at Patagonia. It wasn’t until I jumped [over] to Old Navy that I moved into design. Todd Snyder was head of design there at the time and gave me an opportunity to transition out of merchandising and in to design, where I was responsible for men’s active wear. After that I was briefly at Vineyard Vines, where I helped create and launch their debut clothing line, rounding out the tie and bag collections. Then came my time at J.Crew, where I was for nine years, starting as a designer of men’s bottoms and denim before transitioning to senior director of men’s wovens, footwear, and accessories by the time I left. And then one day, Andy Dunn came knocking at my door with the opportunity I couldn’t pass up, and three years later, here we are.

Dwight Fenton

Dwight Fenton | Bonobos

CS: Whether getting dressed yourself or designing for the Bonobos customer, what’s the one style rule you always follow?

DF: Making sure clothes fit properly, hands down. It doesn’t matter what you spend on something, if it doesn’t fit properly, you’re not going to look good.

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

DF: A pair of nice, nondescript, non-track, sneakers, like Common Projects or Zespa; great, well-fit suit; pair of slim jeans; stable of well-fit solid, non-logo t-shirts; and an unconstructed blazer.

CS: What’s the one thing every stylish, modern man should invest in? Why?

DF: Hands down, a well-fitting suit. Guys always look their best in a suit, plus that one suit can be worn three ways: just the jacket, just the pants, or altogether. And the range of a suit is vast — from a knit shirt and sneakers to tie and dress shoes — it can be the most versatile thing a guy owns.

CS: Bonobos started as a way to help men find the perfect fitting pants. What’s one rule of thumb for finding the perfect fit Cheat Sheet readers should follow?

DF: Pants, our foundation and Bonobos’s signature item, are an item that guys get wrong too often. It starts with the right waist size, which should gently grab your hips and stay in place without a belt. All Bonobos pants are made with our contoured waistband, which was created to effortlessly sit on your hips. Too tight and the waist band pulls, causing drag lines and the fly to show, and too loose will sink and then bunch up under your belt. Once you get the waist right, guys can pick their fit preference. At Bonobos, we offer five fits: tailored, slim, straight, athletic, and boot. I recommend guys try the slim or tailored for a more modern look, but again, it’s all preference. The last thing guys need to keep an eye on is the length which I suggest they keep on the shorter side, showing a little ankle/sock, it keeps the clean lines of the pant while again, adding a touch of the modern.

Bonobos shirts

Bonobos shirts | Bonobos

CS: One thing that’s so interesting about Bonobos is its emphasis on e-commerce. How do you think that’s changing the modern man’s interaction with fashion and creating their own personal style?

DF: More than just an emphasis, it’s the heart of who we are as a brand. Bonobos was founded on the idea of bundling great fitting men’s clothes with exceptional customer service online, and that still continues to be what keeps us going today. What we’ve ultimately done is found a way to present clothing guys love to wear in a space that’s easy to use so they feel comfortable shopping. The guides work with them one on one to help them define their style and look better no matter what the situation. We become their one-stop style resource.

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

DF: I hope we continue on our current trajectory, getting the word out about fit and winning fans along the way!

Follow Kelsey on Twitter @KMulvs