“Most men are reluctant to wear them, because it can look bulky and lumpy if you’re not sure how to [fold] it,” says the New York City-based image consultant, who likes the accessory as a more casual (but still spiffy) alternative to the tie. When she had a celebrity client appearing on TV, she says, she would “sew an index card into the square so they could just put it in and it wouldn’t budge.”
Now, she has a better solution: Earlier this month Sanders and her business partner Christina Wilson launched Well Suited New York City, a collection of pre-folded, fused-together silk pocket squares. Available online, the squares come in several styles, colors and patterns, such as gingham and floral jacquard, and retail for $79 for a box of two.
“All my celebrity guys were like, ‘This is genius!’ ” says Sanders, who had Chris Rock, Jeff Goldblum and Ted Danson test out the accessory.
But it’s not just pocket squares: Men these days are struggling with a number of sartorial challenges, from tying a tie to matching their socks with the rest of their outfit. And there are a whole slew of new products and services ready to help them out.
“You don’t want to generalize and sound sexist, but yeah [men have trouble dressing themselves],” says Vic Cipolla, a spokesman for SprezzaBox, a 3-year-old monthly subscription service that offers guys an array of accessories that can all be worn together. SprezzaBox’s founders were inspired by children’s clothing line Garanimals, famous for its matchy-matchy, animal-printed separates that allow kids to put together their own ensembles.
“Each box has a specific theme, so that everything that comes in a box makes sense all together,” says Cipolla. “It’s idiot-proof.”
Personal stylist Nicola Harrison says that many of the men she works with do find dressing “intimidating,” particularly since they go to work and see their bosses in jeans and hoodies — something their fathers, who helped make casual-Friday dressing appropriate all week long, championed.
“It’s not really that [men] are looking for these shortcuts, but sometimes I feel like they’re losing the art of dressing well, or never learned it to begin with,” says Harrison.
“Fathers used teach their sons how to dress and pass that knowledge down, but they stopped doing that as much,” she adds. “This generation doesn’t have role models or mentors they can look to for how to dress. Even movie stars — who looked so dapper in the 1950s — don’t dress like that anymore.”
That’s the case with Michael Becker, a 42-year-old who works in the hedge fund business. “[Dressing] wasn’t really something I learned about through a parent,” says the Upper East Side resident. “I think it was through moving to New York City and working in the financial world that over time I learned to take more pride in my appearance.”
Still, he has his limitations: “When it comes to tying ties and pocket squares, I’m probably not the most skilled.”
Other guys just don’t want to spend their mornings fussing over their outfits.
“I always liked the idea of a pocket square, but it was like: Do I have time to putz around to make it look right?” says Jon Joseph, an outsourcing exec who lives on the Upper East Side.
The 45-year-old had a change of heart when Sanders gave him a Well Suited square prototype two months ago. Now, he wears them in lieu of ties to work. “It saves the minute or two it takes to [make a traditional pocket square] look right,” he says. “It’s just grab and go.”
Some men’s sartorial problems are more quotidian.
Take Tucked Trunks CEO Rafael De Oliveira, who came up with the idea for the product while working as a medical biller in Westchester — and struggling with his suit.
“I constantly found myself late to work, because I would tuck my shirt in, fix my hair and then, boom, my shirt was untucked again,” says the 30-year-old. He had seen guys tuck their shirts into their underwear to help, so he developed a boxer brief with slip-preventing rubbery dots on the inside of the waistband (similar to what you’d see on the bottom of kids’ grippy socks) that would keep his shirt from spilling out.
Julie Rath, founder of men’s-style consulting firm Rath & Co., says some of these hacks are great, but others seem “gimmicky.”
“We’re all busy, and I’m all for anything a guy can do to take the internal questioning out of his morning and get him out the door sooner so that he can focus on what he does best,” says Rath. But “some of these . . . are more trouble than they’re worth.”
Plus, some guys like having to work for sartorial perfection.
“There is something to be said about the actual process of ‘suiting up,’ ” says James Eng, a 40-year-old arts administrator who lives in Chinatown. “Taking the time to get dressed and knowing throughout the night that you tied that perfect bow tie will give you that boost in confidence. And that’s probably the best accessory one can have.”