The New Old Way to Get Dressed

J. Hilburn’s personal stylists help the menswear brand’s customer customize. A little feminine guidance goes a long way.

There are certain fashion statements men tend to hear again and again: No white jeans after Labor Day. Don’t mix black and brown. Getting custom clothes is a pain in the ass. These truisms may have once been true, but this little thing called modernity happened, and now they’re just isms. The first and second stopped making sense when designers started getting comfortable with not having everything match. The third has been rendered false at least in part by J. Hilburn, the accessible brand that makes all the time-consuming tailoring quick, easy, and—this is the really impressive part—enjoyable. 

The interesting thing is that J. Hilburn doesn’t rely on newfangled scanning technologies. To the contrary, the brand is all about the old-school, employing personal stylists that come to the customer, visiting offices and homes so that men can look on point while staying on schedule. According to creative director and VP of product Jon Patrick, selling to men is all about building trust and incrementally making progress. “Years ago, many of our guys were into just a blue or white shirt. Then we took the next step and introduced them to perhaps a lavender shirt,” he says. “They get compliments at work, and they like the way that feels. So they feel more comfortable stepping out of their shells a bit.”

It doesn’t hurt that the stylists helping men step out of their shells are mostly women. Angela Costales, a classic beauty who works for J. Hilburn when she isn’t at her demanding day jobs, explains that men often crave a bit of feminine guidance.

“I think women make great stylists because there’s an added comfort level to having a woman do a fitting,” Costales says. “We’re good at having distracting conversation, talking to the client about their life, making them comfortable. I have one client on the Upper West Side who doesn’t get off of work until eight, so every now and again I’ll trek up there at nine at night, we will have a glass of wine and pick out some great clothes.”

But don’t get it twisted. J. Hilburn may employ nearly 3,000 predominantly female personal stylists, but what really draws in their customers (and keeps them coming back) is not the chance to have a woman measure their inseam. What makes the whole experience work is variety: The brand offers a staggering number of options. Want a shirt? Great! What sort of fabric, collar, cuffs, back pleats, buttons, plackets, and yokes do you want? If you’re most guys, you don’t know. Angela Costales is there to walk you through the choices.

And Angela Costales is good at her job—so good, in fact, that several of J. Hilburn’s competitors are trying to poach her. She’s not having it: “Other company models would have me push product down people’s throats. That’s not for me.” She’s less interested in the sale than she is in being a resource to men trying to look their best. She has the unique privilege of measuring success in repeat customers rather than sales.

Photos by Getty Images