Think Yiddish and dress British. That was the parting advice proffered by my 8th-grade history teacher, Mr. Weintraub. While his spiels on the American Revolution have long faded from memory, this pearl of sartorial wisdom has endured well into my adult life. Clothing trends come and go—the edgy and stylish of today become the stale and passé of tomorrow—but there are some things that never go out of style.
Clothing and accessories that normally get the label of “classic” might evoke images of country clubs, boarding schools, and swarms of WASPs, but you don’t need to be a scion of old money to embrace a timeless look. Craftsmanship, durability, and understated luxury hold universal appeal, and are the reasons why brands like Brooks Brothers, Vineyard Vines, and Rooney and Bourke have stood the test of time.
“Fast fashion is what I call ‘hangar-pretty,’ clothes that look good for a few months but beaten up after only a few dry cleanings,” says Mark Metzger, the owner of Highcliffe Clothiers, a haberdashery in Middleburg, Virginia. “Preppy brands are usually expensive, but you’re investing in well-made attire that looks good for years.”
Fortunately, I opted long ago to forgo the headache of staying abreast with fashion trends, instead building a wardrobe immune to the whims of the Style Gods. The preppy stalwarts of my closet—Oxford shirts, herringbone sports jackets, hand-crafted footwear—look as sharp today as they did a decade ago. Hell, they’ll still look great when I pass them down to my son. Better yet, prioritizing quality over quantity has saved me plenty of money in the long run.
For a look that doesn’t fade these clothing lines offer a medley of vintage and modern prep. Apart from panache, the throughline in all these brands is an unflagging commitment to masterful craftsmanship and the highest quality material.
New England’s pleasure island par excellence, Martha’s Vineyard is synonymous with the New England dolce vita with glorious summer days of sailing, tennis, and golf. Founded by two investment bankers who were tired of spreadsheets and pining for a more creative pursuit, Vineyard Vines initially specialized in whimsical neckwear like ties bespeckled with patterns of martinis, tennis rackets, and the brand’s iconic pink whale. In recent years, Vineyard Vines has grown into a comprehensive clothing line, spanning from swimwear to formalwear.
Donning my Vineyard Vines Herringbone Greenwich Blazer, a gorgeously detailed tweed jacket, is reason enough to look forward to the autumn’s crisp weather. Tailored with sumptuous British wool embellished with a subtle chevron pattern, the blazer is a dashing complement to chinos, corduroys, or jeans. The interior lining conceals a handy array of pockets for stashing a book, sunglass case, flask, or business cards. Another mainstay of my fall wardrobe is the Mountain Sweater Quarter Zip, a handsome fleece available in playful colors like Nantucket red or forest green. From tailgates and strolls on the beach to air travel, I practically live in my quarter zip from late August to November.
If I had to select a single pair of boots to wear for the rest of my earthly tenure, I would choose, hands down, Red Wing’s Iron Rangers. Made in Duluth, Minnesota, a Lake Superior port city where winters are long and harsh, Red Wing has purveyed rugged footwear since 1905. Yet the company isn’t just for workwear, and its attention to detail and quality follows through everything the brand makes. Iron Rangers are non-pareil work boots, but the sleek design, beautiful leather, and glinting metal trim make them as appealing to those living in Brooklyn as they are to a Lake Superior longshoreman. While lesser boots lose their luster with frequent use, Iron Rangers age like fine wine, the leather picking up a pretty patina over the years. Iron Rangers come in a range of muted colors like slate, amber, and hawthorn, but the black boots are particularly debonair—especially paired with dark jeans. In addition to Iron Rangers, Red Wing sells superb Chelsea boots and leather accessories like belts and wallets.
Dooney & Bourke
Dooney and Bourke might be best known for ladies’ handbags, but the company’s impeccable leather, artful metal trim, and hand-stitched seams translate to equally desirable men’s goods. With a clean design, rich leather, and sturdy brass buckles, the Florentine Hunter Messenger, inspired by vintage mail-carrier bags, makes for a tasteful finishing touch to business casual outfits. The bag’s interior, lined with royal blue fabric and leather trim, is honeycombed with specialized pockets: slots and crannies for pens, chargers, notepads, and laptops. Here is a bag that will last for life with proper care. To complement my Florentine Messenger, I wear Dooney and Bourke’s Explorer Sport Watch, a snappy chainlink timepiece. Leather connoisseurs will likewise appreciate Dooney and Bourke’s wallets, watchstraps, and belts.
Ever since James Dean rocked a pair of wayfarers in the 1955 landmark film Rebel Without a Cause, this style of shades has been a fashion mainstay. Shwood Eyewear, a sunglasses company out of Oregon, reinterprets this classic look in its Ankeny line with frames of Italian acetate inlaid with wooden trim. The Ankeny shades are versatile—dapper with beachwear or formal attire—but particularly clutch for travel, providing ample UV protection and a touch of incognito swagger. Whenever I attend an outdoor wedding, I keep a pair of Ankenys in the inner pocket of my tuxedo. I am partial to the tortoiseshell frames (the look Bob Dylan favored in his younger years), but Shwood offers a range of colors and patterns. Shwood reading glasses are as natty as their sunglasses.
Brooks Brothers is one of America’s oldest and most iconic clothing companies that has thankfully survived changing hands in recent years. Founded in New York City in 1818, Brooks Brothers has been a bellwether of high-end men’s fashion for more than two centuries—a clothier favored by luminaries ranging from Abraham Lincoln and Franklin D. Roosevelt to Ryan Reynolds. Perhaps the key to its longevity, Brooks Brothers straddles tradition and innovation, adhering to time-honored looks while experimenting with cutting-edge fabrics.
Every guy over 30 should invest in a tuxedo—a requisite for black tie dinners, weddings, and galas—and, for my money, Brooks Brothers’ tuxes boast the best value on the market. While Brooks Brothers sells flashier tuxes in hues like royal blue and white, I like the classic Regent Fit One-Button 1818. Cleaving to the traditional look of solid black, satin lapels, and flat-front pants, this suave suit wouldn’t have been out of place in the repertoire of JFK.