How Cole Stevens Helped Sebastian Build a Wardrobe That Actually Works
Most men don’t need more clothes. They need a system — a handful of pieces that work together, a few that stand out, and the confidence to know the difference. That’s what Sebastian Westerink came to StyldLife stylist Cole Stevens to build. And with a Maui trip two days out and an outlet stop planned on the way home, the clock was ticking.
This was their second session, and Cole came prepared. He’d built a four-page style reference — his “West Coast looks” — and walked Sebastian through it image by image, reading his reactions to map out exactly who Sebastian wanted to be in his clothes. One page, “Coastal Prep,” landed hardest. Cole had built it with Sebastian in mind, and it showed: the relaxed-but-intentional look — a gilet over a knit hoodie, a jacket paired with a bucket hat, brown loafers and glasses (the “boss look,” as they agreed) — was him. The country plaids and preppy “yuppie” colors were not, and Cole clocked both without a trace of judgment.
What Cole teaches isn’t a shopping spree. It’s a capsule wardrobe — a foundation of pieces you wear for years (good jeans, a few tees in white, gray, and navy, a handful of button-ups) with the occasional standout layered in. “I promise I won’t make you buy white jeans yet,” he told Sebastian, laughing — the mark of a stylist who meets you where you are instead of where a trend insists you should be.
The advice was specific and quietly practical. A loafer, which Cole recommends to every client, because it dresses an outfit up or down — even with shorts. A good wool trouser worn casually to dinner, because “dress pants” is an outdated way to think about a great pair of trousers. A long-sleeve button-up with shorts, a classic combination most men overlook. None of it complicated once someone who cares takes the time to explain it.
Then there was the trip. Two days from Maui, with a stop at the Vacaville outlets, Sebastian needed hot-weather pieces fast — and Cole turned coach. Two pairs of chino shorts, navy and gray. Cotton button-downs in long and short sleeve, with a camp-collar option for the tropics. A fresh pair of solid swim trunks to retire the pre-COVID pair. His brand call was refreshingly honest: J.Crew for quality right now; J.Crew Factory if the outlet clock demands it — “the H&M version of J.Crew,” he admitted, but fine in a pinch.
Before their next session, Cole would build Sebastian a Pinterest board — capsule basics first, then the statement jackets, the loafers, the bucket hats. Because the point was never a single great outfit. It was a way of getting dressed that keeps working long after the call ends, and a client who finally understands why each piece earns its place.
Sebastian did all of this from California; Cole, at the time, from Seattle. No store, no cross-town appointment, no guesswork — just two screens, a reference doc, and a stylist who made building a wardrobe feel less like a chore and more like figuring out who you already are.
Meet your stylist: Cole Stevens — fashion & wardrobe stylist, now based in New York City. Book with Cole →
This story reflects a real, paid StyldLife client session. To protect our client’s privacy, the client is not pictured.