Strapping Style

When a watch strap is dismissed as an afterthought, interchangeable and seldom reconsidered, it is often because its influence is understated, even as it quietly determines whether a watch feels intentional or unresolved. But to menswear designers, stylists, and critics, the right piece of metal, leather, or fabric can serve as a bridge between watch and wearer, jewelry and clothing, formality and ease.

“I think about a strap on a watch in the same way that I think about clothes on my body,” says Mark Cho, cofounder of The Armoury. “You’re dressing it up, trying to speak its character.” The right strap, he argues, can transition a watch from “a tiny little object on its own” into something that coheres with everything else you’re wearing.

“Watches sit somewhere between jewelry and functional clothing, which makes them incredibly personal,” says menswear writer Derek Guy. For that reason, straps allow a piece to modulate among different contexts with ease. With a proper strap collection, one watch can read as casual or formal, conservative or expressive, depending on how it’s integrated – or not – into the overall vibe.

Across tailoring ateliers in New York and Florence, streetstyle influencers, and global fashion weeks, the rules of matching straps and watches turn out to be less rigid than they appear. Sometimes coherence means harmony: matching texture, tone, context. Other times it means contrast: a sports watch softening a suit or a dress watch grounding denim. “It’s like food,” says Guy. “If it’s good, it’s good.”

Here, Cho, Guy, and other menswear stylists and mavens talk through why certain strap choices work and what these minor sartorial details communicate about a larger sense of style.

One practical tip Cho returns to is color adjacency. “Whatever you put next to a dial or case is going to affect your perception of that color,” he explains. Tan and gold may be a classic pairing, but the exact shade matters.

“A. Lange & Söhne’s Honey Gold is incredibly delicate – somewhere between white and deep yellow,” Cho says. “You don’t want to overwhelm it. Lange’s argenté dials can read too silver to me, so I’ll put them next to something yellowish to warm them up.”

The Type 4A, which Cho co-designed with Naoya Hida, received the same attention as the watch itself. “There was this talented old maker of cordovan straps in Japan. I bought everything he had left,” Cho says. “Cordovan is hard, almost plasticky, which gives the deep brown a purply richness. The dial is more charcoal than black, with bright ivory numerals; it’s very sleek, like car paint.”

For the Type 2C-1, the strap highlights subtle dial details. “The numerals are hand-engraved and filled with a faint blue lacquer, so I wanted to draw that out,” Cho explains. “We were the first to use shrunken calfskin, which you usually see in linings. Too much interlining flattens the grain, and you lose what makes the texture interesting.”

“When a watch is jewelry-esque, you have to lean into that,” Cho says. He cites the Louis Vuitton Tambour as an example. “The original strap wasn’t for me. The case is so smooth that it needed texture and color, so I chose a dark-brown python with mottled shading.”

The same thinking shaped The Armoury’s 18k Cartier bracelets. “Our tricolor mosaic bracelet was inspired by the Mosaic Tank dial,” Cho says. “Brick-style bracelets work on almost everything, but this one was meant for a very specific reference.”

Cho favors exotic leathers when they add nuance rather than flash. Ostrich, he says, works especially well on vintage watches. “It looks a bit like crocodile, but with matte and shiny variation, almost like patinated alligator.” Lizard skin offers a similar restraint. 

On a Vacheron chronograph, stingray introduces texture against a flat dial while remaining “very easy to wear, especially in the summer.” Cho admits the leather is divisive. “It’s not for everyone, but on a formal watch, you look for subtle ways to make it interesting.”

For Takahiro Osaki, creative director of Liverano & Liverano, straps ease with transition. “This Orvis dual-time dress watch on leather elevates denim without making it stiff,” he says. “That touch of particularity is the difference between a predictable look and one with personality.”

Osaki often uses straps to soften formality rather than reinforce it. A steel sports watch on tailoring, or a dress watch on casual clothes, works when the materials speak to each other.

“Sports watches do the opposite,” Osaki says. “They soften formality while maintaining chromatic or material coherence.” A vintage Seiko 5 on a three-link bracelet succeeds not because it follows rules, but because it creates a dialogue.

“It’s a game of balanced contrasts,” he says, explaining that he doesn’t look for formulas, but for “combinations that just make sense.”

Guy notes that contrast is risky but powerful, and difficult to get right. “There’s something charming about a detail that looks slightly off,” he says, invoking Bruce Boyer’s definition of sprezzatura: “I could have looked better if I’d tried.”

Here, Osaki’s inverted suit of tan solaro, traditionally worn on the inside of a jacket, lowers the formality enough to make a steel bracelet feel natural. “It’s tailored beautifully,” Guy says, “but not business-formal – that’s why the bracelet works.”

Guy also says beads-of-rice bracelets, like the one on Osaki’s 1970s Seamaster, are a great way to elevate a “clean and contemporary” look of jeans and a t-shirt. “They’re great at bridging casual tailoring and everyday wear.”

For Guy, the right strap is often what makes an outfit feel properly assembled. “Tailoring comes in a wide range of seasonal fabrics, stylistic details, and cuts that can change the meaning of the garment,” he says. “The watch should be suited to the level of formality you’re conveying.”

Here, Dan Roan wears a gold Universal Genève Polerouter on an exotic brown leather strap. “I like dress watches on flat leather straps, without too much interlining,” Guy explains. “The folded edges and lack of visible stitching break up the smooth textures while still looking very dressy.” The result has a distinctly midcentury feel – —“which really complements the Polerouter, a fantastic dress watch for the value.”

Guy is generally skeptical of sports watches worn with tailoring. “As formality goes up, leather usually looks more coherent,” he says. “We have so few opportunities to look elegant that it seems like a wasted opportunity.”

Still, context can override convention. At Pitti Uomo, Guy’s podcast co-host Peter Zottolo paired a Rolex Explorer I on an Oyster bracelet with a lightweight summer cloth and a nearly see-through polo. “This is not an office appropriate suit,” Guy laughs. “It’s casual, almost sleazy – and a great example of where a steel bracelet totally works with a tailoring.”

Sergio Loro Piana’s black Swatch has historical precedent. Guy recalls menswear Tumblr’s Italian Industrialists and Intellectuals, where powerful men wore conservative suits with playful watches in a style Guy calls “reverse snobbery.”

“In certain industries, everyone can afford a six-figure watch,” Guy says. “The flex becomes saying you run marathons and have free time.” Still, he adds, Swatches aren’t only ironic. “They’re just fun. I wouldn’t wear one with a tuxedo, but on a day in the park, that can be charming.”

As an added bonus, playful straps offer a cheap ways to experiment with color, Guy says, pointing to the Michael Hill, the creative director of Drake’s who’s often seen sporting bright red and yellow Swatches. “A bright strap is an easy way to inject personality,” Guy says. It’s the difference between performing reverse snobbery and simply not being snobbish.

“Does a waffle-knit henley and denim western shirt work with a houndstooth tweed coat?” Guy asks. “Rules-based guys will say never.” But shared workwear roots make the combination compelling.

Creative director of Fortela, Alessandro Squarzi’s vintage Submariner completes the look. “The tropical dial and ghosted bezel pick up the outfit’s colors,” Guy says. He acknowledges you have to be deep into watches to appreciate a pairing like this, but that’s exactly the point. The match signals an underlying taste pulling everything together.

Guy says it's easier to spruce up a casual outfit with a dress watch, than to use a sports watch to dress a suit down. On the left, Squarzi pairs a Blueberry GMT with fatigues for a classic workwear combination. Guy say contrasts the style with a similar look by his friend on the right. "He's very soft-spoken and demure," says Guy, and so even paired with selvedge jeans and a field jacket, his gold Cartier Tank works.

Guy never expected a Datejust to work with a denim jacket. “I inherited my father’s Datejust, and I’ve always thought of it as a dressier watch,” he says. “With a denim jacket, I’d normally reach for a 1016 or a Sub.” But the Jubilee bracelet changes the equation. “Generally, finer bracelets read more formal, chunkier ones more casual—but a Jubilee can go a lot of different ways.” Here, it bridges the gap.

For field watches, Guy sees no reason to depart from the classic NATO strap. Earthy tones like olive, khaki, gray, and black, look best, especially on military-issued pieces like his Omega Dirty Dozen, which he wears on an olive AF0210 in cotton for comfort and authenticity. But the affordable straps also invite experimentation. “It’s easy to get carried away with NATO options, but they’re also relatively affordable and easy to change out.”

Joseph Pollard, the founder of August Loafers, is a former creative director at RRL, where these leather and suede NATOs, mounted on early Submariners, were a passion project. “It’s only natural he’d choose them,” Guy says. “There’s something about this look that feels like it shouldn’t work on paper – dive watches on leather, loafers with fatigues – but it does because all of it traces back to the history of how these items were originally used.”

“Smashing traditions together is just classic American menswear.”