Back in my boarding school days, I served detentions for refusing to wear a school-issued necktie. Saturday mornings in rural New England found me languishing in cold, musty classrooms alongside fellow dress code dissidents. With God as our witness, we swore a solemn oath together: once graduated, we would never again allow silken shackles to discomfort our throats—the noose before the necktie, by Jove!
Like John McCain in the Hanoi Hilton, I kept my pact with my comrades. Years came and went, and my neck remained bare at funerals, weddings, and job interviews. But, alas, I craved a splash of color in my business-casual attire. Fortunately, I learned the ways of the pocket square.
On a recent jaunt to Nantucket, I sat down with Vineyard Vines designer Eric Vos to better understand this subtle yet sophisticated masculine accoutrement. “Especially if you’re skipping a tie, a pocket square adds a pop of color and texture to your outfit,” he told me over martinis at Cru, a bar near the harbor. “Choose one that pulls in or complements the colors in your jacket. When in doubt, solid white linen is a safe bet.”
I griped about having to learn intricate folding techniques, but Eric assured me that less was more. “You don’t need anything fancy to make a statement. Even after learning complex folds, I stick to the classic flat fold—simple, clean, and quick. The ‘poof’ is another arrangement that only takes a few seconds.” Rocking a light pink, whale-patterned pocket square in his Vineyard Vines blazer, Eric cut a profile as dashing as the commodore of the Nantucket Yacht Club.
A pocket square serves as a final, debonair flourish whenever I throw on a sports jacket—be it a navy blazer, a seersucker suit, or a tweed coat. It’s a humble accessory that punches above its weight for broadcasting stylishness and élan. Here are a few of my favorites.
Photo via Vineyard Vines
Vineyard Vines
After meeting with Eric and envying his outfit, I drained my martini and tried to pass off the soiled cocktail napkin as a pocket square. The waiter promptly ejected me from the premises, but luckily, the Vineyard Vines shop was just a few blocks away. I bought several silky squares of playfully patterned fabric: a rose-hued pocket square with tiny sailboats, a lime-green number with lighthouses, and, fittingly, a crimson one festooned with mini martini glasses.
The pastel colors pair beautifully with my blue blazer. Airy yet tightly woven, the silk is so fine it would make a Ming emperor’s robes look cheapjack. Eric advised me to wear just one bold color per outfit, lest I look like I’m wearing an Easter Bunny costume. Keeping his advice in mind, I sport a white linen pocket square when I wear my pink linen blazer from Vineyard Vines or my seersucker suit from Alan David Custom Tailors.
You don’t have to launder a silk pocket square often, but when you do, hand-wash it in cold water with a gentle detergent.
Photo via Robert Talbott
Robert Talbott – Collins Pocket Square
As a New England nationalist, I tend to shun California’s sartorial taste, but the men’s attire from Robert Talbott, a company out of sunny Carmel, is irresistible. The aesthetic blends East Coast prep with West Coast laissez-faire—a bit like my boarding school buddy from San Francisco.
Made from Italian fabric, the Collins Pocket Square features differing patterns on each side—it’s like two pocket squares in one. The Collins comes in an array of handsome colors, but I like the light blue. It pairs well with any of my blazers, even jaunty pastels or seersucker. The pattern—squares interlaced with diamonds and florets—brings to mind the sacred geometry of Persian mosques.
Photo via Tom Ford
Tom Ford
I salute Tom Ford, the small-town Texas boy who struck it big in high fashion with his impeccable taste and razor-sharp business acumen. Mr. Ford’s suits are beyond my budget, but I can afford a pocket square from the legendary fashionista.
Tom Ford’s pocket squares come in both neutral tones and elaborate patterns. I’m partial to the simpler designs, and I scooped up a light pink square with small white polka dots. It’s my stalwart when I wear a striped suit—like seersucker or classic pinstripes.
Photo via Gentleman’s Gazette
Fort Belvedere – Wool Pocket Square
We’re a long way from tweed season, but when the weather turns crisp, I look forward to sporting my woolen pocket squares. The visual texture of tweed is too coarse for silk, but wool pocket squares look fly as hell in that jacket you picked up in Edinburgh.
Fort Belvedere, a luxury men’s brand from Germany, purveys gentlemanly accessories like cufflinks, boutonnières, and kid leather gloves. It’s beautiful stuff—garments fit for a Central European aristocrat with a last name as long as a sentence.
When I wear my tweed coat—also from Vineyard Vines, mind you—I pair it with my Fort Belvedere burnt orange pocket square: the color of the foliage in late autumn on a drive through Vermont. If you’re not planning a trip to Deutschland anytime soon, you can purchase Fort Belvedere’s fine wares through Gentleman’s Gazette, a superb online haberdashery.
