Wearing a watch is more than just telling time. Whether you’re a seasoned watch enthusiast, someone who enjoys stylish accessories, or a newcomer to the world of watches, there’s a lot to consider when it comes to styling a watch. Should you mix bracelets and watches? Do you coordinate your watch with your outfit? Or do you simply go with what feels right?

Even the most fashionable men on the internet, like A$AP Rocky, Jacob Elordi, and Daniel Craig, wrestle with these questions. Rocky often alternates between bold iced-out Rolexes and elegant vintage Piaget Polos. Elordi swears by Cartier Tanks, while Craig is loyal to Omega. Whether they layer their watches with chains and rings or let their replica watches stand out on their own, these icons offer plenty of inspiration.

To help crack the code of wearing a watch, we asked several watch experts for their tips. But remember: at the end of the day, there’s no one-size-fits-all rule. The way you wear your watch is entirely up to you.

Brynn Wallner: The Loose and Playful Approach

Brynn Wallner, founder of Dimepiece, is known for her unfiltered, straightforward take on watches and accessories. When it comes to style, she’s all about individuality and freedom. Wallner’s one key piece of advice? “Don’t go too big if your wrist is too small.” She stresses the importance of understanding proportions – just like how we dress. A watch should complement your wrist, not overwhelm it.

Wallner is also a fan of stacking, but with caution. “Wearing multiple bracelets on the same wrist as your watch can lead to scratches, which could result in overpolishing your watch.” Her biggest watch-related no-no: “Never stack an heirloom watch.” She’s a fan of the “loosey-goosey” fit, particularly when it comes to oversized or women’s watches worn by men (think Timothée Chalamet in a tiny Cartier Panthère). The relaxed, almost bangle-like fit adds a confident, laid-back vibe to any outfit.

That said, Wallner advises paying attention to the weather. Wearing a leather-strapped watch on a hot day with short sleeves? You might regret it. Just like socks with loafers in the middle of summer, certain combinations don’t work in all conditions.

Adrian Aldred: Unique, Classy, and Personal

Adrian Aldred, the creative mind behind Convopiece, specializes in rare, bespoke watches. He emphasizes that wearing a watch is all about personal expression – but there are still a few guidelines he swears by. “No baggy bracelets, no using watches as hairbands, and no watches that are clearly just for show,” he says. Aldred doesn’t shy away from bold choices, but he believes watches should reflect the wearer’s true taste, not just be status symbols.

When it comes to stacking watches, Aldred is cautious. “If you’re a watchmaker showcasing your work, sure, but in general, less is more.” He suggests pairing a fitness band with a classic sports watch, like a black Nato-strap model, for a coordinated look. Beyond that, Aldred keeps it classy, letting the watch speak for itself.

J.J. Owens: Wear What You Want, But Make It Yours

J.J. Owens, the founder of Daily Grail and a self-proclaimed watch obsessive, believes that wearing a watch should be fun and personal. “It’s not something to overthink,” she says. Owens is firmly in the “loosey-goosey” camp, favoring a relaxed, comfortable fit – especially for women who want to wear a larger men’s watch, like the Olsen twins do with their oversized Rolexes.

For Owens, the beauty of watches lies in their versatility. She loves pairing dress watches with casual outfits, creating a surprising juxtaposition. “Wear a fancy watch with jeans and a T-shirt – why not? Life’s too short, and every day is an occasion,” she says. Whether it’s an iced-out watch or a minute repeater, Owens believes in making your own rules and wearing what feels right for you.

Wei Koh: Keep It Simple and Avoid the Stack

Wei Koh, the co-founder of Revolution, is not a fan of stacking bracelets with watches. “Bracelets slamming into the side of the case just ruins the look,” he says. Koh is a minimalist when it comes to accessories, preferring rings and necklaces to be worn on the opposite wrist. He also believes that trends shouldn’t dictate your watch style. “Because small watches are trending, I’ve rediscovered the charm of a larger, 44mm Panerai Luminor,” he notes. For Koh, wearing a watch should be an expression of personal taste, not conforming to fleeting trends.

Yu Sekiguchi: Protect Your Watch, But Experiment Boldly

Yu Sekiguchi, an expert known for his meticulous care of clone watches, focuses more on protecting your watch than on fashion rules. “Avoid leaving the crown open, and remember that water and magnetism are your watch’s biggest enemies,” he advises. Sekiguchi is a fan of stacking, but with a caveat: it’s a personal choice, and if you plan to sell the watch later, you should consider protecting its condition. “Wear it carefully to avoid scratches,” he warns. But if you’re not concerned about resale value, feel free to get creative with your accessories.

Andrew McUtchen: Avoid the Dive Watch with a Suit

Andrew McUtchen, founder of Time+Tide, believes in keeping things elegant and appropriate. He’s not a fan of pairing large, sporty dive watches with formal suits. “It’s a clash,” he says. But McUtchen’s biggest pet peeve is the double watch look. “Wearing two watches just looks silly, unless you’re an Italian prime minister. No one needs to wear a wife and a girlfriend at the same time,” he quips.

Dillon Bhatt: The Elegance of Contrasts

Dillon Bhatt, founder of LuxForte, believes that how you wear a watch should be a reflection of your personality. That said, he’s strict about the pairing of fake watches with formal attire. “Bulky dive watches or sports watches don’t belong with suits,” he insists. However, he loves the contrast of wearing a small, elegant dress watch with casual clothing. “A refined watch can elevate a laid-back outfit, like oversized jeans and sneakers. It’s all about the balance.”

The Only Rule Is Your Own

While experts may disagree on some points, there’s one thing they all agree on: there’s no right or wrong way to wear a watch. Whether you’re stacking, wearing a formal watch with casual clothes, or embracing bold styles, the key is to make it your own. As long as you’re wearing your watch with confidence, you’re doing it right.