The Rise of Sport Watches at Formal Events: Breaking Style Rules in 2025

The high society of previous generations followed a clear set of sartorial rules. Dress codes were firmly established, and what one wore to a formal event was not a matter of interpretation. Today, those norms have softened. Tastefully breaking the old guidelines is now particularly evident in the world of watches.

Where once a slim, gold, time-only dress watch was the only appropriate choice with a tuxedo, modern formalwear often features sportier models. It is increasingly common to see Daytonas, Submariners, and other tool watches on the wrists of guests at weddings and black tie events.

This cultural shift raises an ongoing question among watch collectors and style observers: is this relaxed approach to formality just a fleeting trend, or has the definition of appropriate watch pairings evolved permanently? With dress watches now appearing with jeans and divers worn alongside tailored suits, the traditional boundaries have blurred.

Jeremy Freed, a style and watch writer at GQ, said this evolution reflects a larger cultural moment. “We’re living in a time of unprecedented plurality when it comes to getting dressed,” he said, “and the rules around what watch is appropriate for what outfit have evolved along with everything else.” In this context, watches function less as strictly coded accessories and more as expressive elements of personal style.

Freed acknowledged, however, that the absence of clear rules demands both discernment and confidence. “You need the taste to make the right call and the confidence to pull it off,” he said. “When you take away the guardrails of convention, there are a lot more places to mess up.” Without traditional guidance, the margin for stylistic error increases. A mismatched watch can stand out in ways that undermine rather than enhance an outfit.

Rather than ignoring the old rules altogether, Freed said he uses them as a starting point. He pointed to contemporary options that honor the spirit of formality while still pushing stylistic boundaries. For example, in place of a classic Calatrava, one might opt for an annual calendar on a leather strap or a fumé dial from brands like H. Moser & Cie. These alternatives offer visual interest and individuality while maintaining a refined sensibility.

Ted Silver, owner of the well-regarded haberdashery Weiss and Goldring, took a more traditionalist stance. Known for outfitting clients from Louisiana’s social circles to PGA Tour professionals, Silver favored a segmented approach to watch pairing. “Understated elegance is always better than being the loudest man in the room,” he said. “A watch is like a fine cologne. You want people to come closer to notice it, not get the full story from across the street.”

According to Silver, versatility is important, but not at the cost of appropriateness. His advice for those who own just one watch is to evaluate their wardrobe. “Get a watch that works with 70 percent of what you wear,” he said. “That way, you’re only off-base 30 percent of the time.” Ideally, a collection would include at least one dress watch and one sport model, but he recommended investing more heavily in the one that aligns with daily attire.

Even so, Silver allowed for sports watches in relatively casual settings. “With a sport coat, no tie, and sneakers? An Aquanaut, Daytona, or Royal Oak is great,” he said. “Just don’t confuse that with a suit. If you want to channel Sean Connery for the night, wear a Submariner. Otherwise, go with something classic. A leather strap, three hands, maybe a subtle complication. Elegant, refined, and never out of place.”

Looking ahead, the direction of broader style conventions remains uncertain. Freed suggested that the momentum is likely to continue in favor of informality. “The arc of menswear has been bending toward less formality for the last century,” he said, “and I don’t see that changing. That said, the pendulum does swing back to traditional tailoring and its attendant conventions every so often.”

Whether one leans toward modern pluralism or timeless restraint, the throughline is clear: intentionality matters. Thoughtful pairing of watch and wardrobe remains essential. Freed’s and Silver’s philosophies may differ, but both reflect the same fundamental idea, that how a watch complements an outfit still carries meaning, even in an age where the rules have loosened.