There are few celebrity wardrobes as studied—or as imitated—as the Olsen twins’. And in a market crowded with disposable celebrity projects, The Row has somehow transcended into a fashion religion, complete with an altar built on discipline and longevity. The watches Ashley Olsen has worn over the years reflect that same sensibility—pieces chosen for proportion and integrity in both design and material. Here, each one is broken down with its historical and stylistic significance.
YELLOW-GOLD ROLEX DAY-DATE
Deliberate and restrained, the Rolex Day-Date holds a certain cache in watch circles because of its integrity. Introduced in 1956, the Day-Date represents Rolex at the brand’s most distilled: clean architecture, mechanical prowess, no excess. It’s offered only in precious metals and paired with a bracelet known as the “President,” a name earned through its association with heads of state and industry leadership.
On Olsen, the slightly oversize proportions echo the same rigor that underpins The Row: precise yet easily wearable.
THE APPLE WATCH
They say good taste is developed through living a full life, and on anyone else, the Apple Watch is another digital interface that begets the question: Do you really need another screen? This one at least takes its design cues from Cartier’s first wristwatch, the Santos.
And on Olsen, fashion disciples can understand that the Apple Watch, on a Sport Band no less, has earned its place. This is the tension that keeps her style alive, not preserved. Even the most discerning eyes don’t question the convenience of modern-day technology!
YELLOW-GOLD ROLEX DAYTONA
First introduced in 1963, the Daytona was built to time laps at Florida’s Daytona International Speedway. Once for professional racers, now for those who appreciate a sporty edge as they get dressed (and knowing the mechanics have actual capability behind it).
The duality of a classic sports watch in a buttery yellow gold on a tiny wrist is entirely the point.
CARTIER PASHA
The Pasha’s origin story is quite specific for Cartier: In the 1930s, Thami El Glaoui, the Pasha of Marrakech, requested a custom waterproof watch that could be worn as he moved from the hammam to the pool. The Pasha remained a one-off until 1985, when Cartier asked Gérald Genta, a legendary watch designer behind some of the most influential watch designs of the 20th century, to rework it. His new Pasha introduced some geometry play: a round profile, the bold numerals, and the screw-down crown cap that defined the model for a new generation.
Olsen’s choice in a monochrome Pasha makes for a cohesive addition to her collection—she certainly gravitates toward dark dials and an oversize profile.
VINTAGE COCKTAIL WATCH
Diamonds, a slim silhouette, and a skinny little strap to match—vocabulary of night but worn in day. This contrast is where the magic lies! An old-world detail slipped into a modern woman’s pace.
Cocktail watches emerged in the 1920s through the 1960s, when women’s timekeeping was as much a collaboration with jewelers as it is watchmaking, and watchmakers answered the market demand with small mechanical movements tucked inside diamond-set cases.
SHINOLA RUNWELL
Shinola launched in 2011 as a venture-backed brand concept to revive pockets of American manufacturing, but it wasn’t until 2013 that it made a watch: the Runwell. It became the brand’s proof of concept—assembling quartz movements in Detroit, bringing back an American watch-assembly line again, and creating a product that’s deliberately straightforward rather than precious.
It isn’t luxury nor collectible, but in Ashley Olsen fashion, it’s certainly oversize and pragmatic. As always, it cuts against her otherwise edited wardrobe and feels intentional only in its simplicity. The lesson here is to leave room for the unexpected!
