I have an origin theory about preppy aesthetics. I’m no sociologist, but my ancestors came over on the Mayflower, and I spent many a long year in boarding schools and the Ivy League. The hallmarks of preppy style—understated luxury, masterful craftsmanship, and generational patina—stem from psychological dissonance that has haunted the descendants of the Puritans.
Cotton Mather and his ilk deplored opulence, but later Boston Brahmins grew filthy rich from maritime trade, railroads, and textile mills. Herein lay the rub: How to reconcile dizzying wealth with an ingrained aversion to ostentation? Flaunt money quietly. Emphasize craftsmanship over ornament. Hint at status so subtly that only “those with eyes to see” may see.
Which brings me to preppy watches. Wristwatches are functionally obsolete in the age of iPhones and clocks on every appliance. And yet we still covet them—nay, we spend beyond our means to acquire them. Why? Because a fine watch, beyond its inherent beauty, whispers elite status and rarefied taste.
The four watches below are so exquisitely preppy they could make even the most somber Puritan dance with joy (which, of course, was a mortal sin). Wear them in Bar Harbor or Chappaquiddick as you reminisce with old chaps about punching final clubs at Harvard.
Photo by Johnny Motley
Shinola Mechanic
Proudly based in Detroit, Shinola is the Great American Watch Company. Even the name alludes to vintage Americana charm. Shinola was a popular shoe polish brand in the mid 20th century, immortalized in the colorful military idiom: “He don’t know shit from Shinola.” Their clean, masculine, and no-nonsense designs evoke the cars and architecture of Motor City’s golden age.
Most Shinola watches use quartz movements, but the Mechanic is hand-wound—a nod to the elegant timepieces of the fin de siècle. The mechanical movement causes the second hand to glide in a smooth sweep across the dial, unlike the ticking of quartz-powered watches. The Mechanic’s caseback is skeletonized, showcasing its whirring metallic viscera. With a dark leather band, sturdy convex glass, and gold trim, the Mechanic is dressier than Shinola’s flagship Runwell. It’s my stalwart for dinner dates or whenever I throw on a navy sport coat.
For a more affordable Shinola, I am partial to the Canfield launched in partnership with Huckberry. It resembles the Runwell but with a splash of rakish color on the dial.
Photo by German Disla
Swatch Captain’s Dream
I’d have to either wife-up an heiress or rob a bank to afford most of the Swiss watches I so covet—but Swatch is the happy exception. A portmanteau of “Swiss Watch,” Swatch cleaves to the meticulous craftsmanship of Swiss horology while eschewing the stuffiness and prohibitive prices. Beloved for their whimsical colors and playful designs, most Swatches clock in well under $1,000.
The Captain’s Dream is the kind of timepiece a young naval officer might purchase upon his discharge for a cushy civilian post—perhaps in finance or yacht brokerage. The case’s gold trim complements the textile strap’s royal blue, a hue that conjures tropical waters and varnished decks. Textile bands are less dressy than leather or steel, but they pair beautifully with beachy chic. Wear it with a guayabera, seersucker shorts, and vintage Persols as you gaze out at the Atlantic from your Hinckley sloop, whispering verses from Lord Tennyson in praise of the sea.
Photo via Kiel James Patrick
Kiel James Patrick’s Newport Adventurer
Based in Rhode Island, Kiel James Patrick epitomizes the coastal New England dolce vita of long summer days of sailing, tennis, and clambakes. The brand purveys jewelry and clothing inspired by the nautical knots and flags of New England maritime heritage.
I love a timepiece that looks and feels far more expensive than it is—and at under $200, The Adventurer meets this criterion with flying colors. With an elegant 30mm face, it flatters men with slimmer wrists. The watch is available with either leather or textile bands. I favor the latter, a comfortable yet durable fabric strap in crimson and royal blue stripes reminiscent of a club tie. The hour markers at 3, 6, 9, and 12 o’clock are enamel nautical flags, and the hands are tiny golden anchors.
Photo via Casio
Casio Oceanus
Few watchmakers have done more to revolutionize modern horology than Casio, a pioneer in digital displays and quartz-powered movements. While Casio’s digital watches are iconic, their analog models are hidden gems that make watch nerds drool. Models like the F‑91W only cost about $20, but Casio also crafts superb luxury timepieces (though they’ll set you back a bit more).
The Oceanus is an ultra-slim analog watch with a brushed titanium band. It syncs via radio with atomic clocks, allowing razor-precise timekeeping. Granted, you don’t need millisecond accuracy unless you’re working for CERN or NASA, but it’s an undeniably slick feature. The dial comes in a spectrum of space-age metallic finishes, but I’m partial to midnight blue. Adorned with lume-coated white pips, the dial looks like photos of deep space from the Hubble. Wear this beauty with a suit or tuxedo and wait for the inevitable James Bond comparisons.
Photo via Huckberry
Honorable Mention: Case Elegance Military Watch Case
What’s the point of building a watch collection if you can’t admire your treasures side-by-side in a neat, satisfying arrangement? A matte-finished steel box, the Military Watch Case is as handsome as the gorgeous timepieces you’ll keep within it. It houses up to ten watches, each cradled on a velvet pillow to prevent scratches and scuffs. The case also comes with a removable holster for Apple Watches, complete with a charging port in the back. I especially appreciate the lower drawer beneath the main chamber—perfect for stashing cufflinks, collar stays, and all the small accouterments a gentleman accrues.
