Dressing up doesn’t mean what it used to. Over the last few decades, dress codes have relaxed in virtually every area of life, from the office to the first-class cabin, leading many to gripe that the collapse of the men’s formal wardrobe reflects the collapse of civilized society. Whether or not this is the case, just because you can substitute a polo for a button-down doesn’t mean you have to. The same goes for your watch. While it’s now totally normal to wear a dive watch (or a smart watch, for that matter) with a suit, there remains an entire universe of dressier options that, in our opinion, will look even better. Here are a few of our top picks.
Tudor 1926 Luna

In the hierarchy of dressiness, leather straps tend to sit several rungs above steel bracelets. As such, while it may not be the best choice to wear with a tuxedo, this steel Tudor meets all the criteria for an everyday dress watch thanks to its clean design and subtle moonphase complication. Plus, there’s nothing stopping you from swapping in a black leather strap for an even more refined look. ($3,740)
Cartier Roadster

The newly re-released Roadster, with its curvaceous design inspired by mid-century automotive details, is among the sportiest members of the Cartier family. Like almost every other piece from the famed Parisian maison, however, it can transition from casual to formal with aplomb. While the steel version is perhaps better suited to its automotive source material, this gold-maxed one is a conversation piece of an entirely different breed. ($73,500)
Bulova NYC Tony Bennett

If anyone understood the value of a good formal wardrobe, it was legendary 20th-century crooner and respected painter Tony Bennett. Rarely seen without his signature dark suit, white shirt and tie, Bennett defined class for generations of music lovers. It stands to reason, then, that this Bulova, created in his honour, pairs with a wide range of tailored looks, from a brown tweed sport coat to a navy-blue suit.($950)
Omega Constellation Observatory

A dress watch in the most traditional sense of the word, the Constellation Observatory is as refined on the inside as it is on the outside, thanks to its Master Chronometer-certified movement. Based on the Constellation models of the 1950s, this recently introduced collection brings forward Omega’s famed “pie-pan” dial for a distinctly vintage look. File under old-school sophistication. ($14,300)
IWC Portugieser Automatic 40

In its most classic form, a dress watch is one with a precious-metal case, a leather strap, and a dial free of date windows, chronograph counters and other such distractions. Watches that meet those criteria are extremely rare these days, but this pared-back version of IWC’s Portugieser, a watch whose design dates to the 1930s, makes a perfect modern substitute. ($30,900)
Longines Master Collection

The beauty of a steel-on-steel watch is its ability to complement just about anything in your wardrobe, from jeans and a T-shirt to your nicest dark suit. Such is certainly the case with the Master Collection, which ups the sophistication ante with the help of blued hands, Breguet numerals and a beautifully textured silver dial. ($3,400)
Frédérique Constant Classics Heart Beat Moonphase Date

Thanks to details like Roman numerals, “pomme” hands, and a barleycorn-textured dial, this Swiss-made watch will complement just about any formal wardrobe. While its design is firmly rooted in the 19th century, its cutaway “heartbeat” window, through which you can see the watch’s automatic movement in motion, sets it apart from the stuffy designs of yore. ($3,195)
Piaget Andy Warhol

While the scale of its 45 x 43 mm 18-karat rose-gold case is anything but subtle, the combination of an onyx dial and a black alligator leather strap is about as stylishly refined as you can get. Should your tastes run a little wilder, of course, you can build your own with a choice of white- or pink- gold case, 12 hard-stone dials, two handsets and five colours of leather. ($77,500)
Citizen Tsuyosa 60 37mm

With its colourful dial selection, Japanese automatic movement and a choice of either 40 mm or 37 mm cases, it’s easy to see why the Tsuyosa is among the most popular pieces in Citizen’s extensive lineup. This version, with a gold-tone case and an ornate guilloché-patterned dial, is the most elevated of the bunch. ($795)
Rolex Oyster Perpetual 41

Released in honor of the Oyster’s 100th anniversary, this thoroughly modern watch encompasses everything that makes Rolex the world’s most famous watch brand. Aside from the water-resistant case that made the Oyster famous, its design language is both simple and refined, from its stick hands and indexes to its rounded yellow-gold bezel. There are dressier watches in the Rolex lineup, but perhaps none that are more versatile. ($12,200)
PHOTOGRAPHY: MARC SANTOS (WESTSIDE STUDIO)
PHOTO ASSISTANTS: SARA FLEISZIG, PATRICK MARCOUX
PROP STYLING: ERICA MORGA(CADRE ARTIST MANAGEMENT)
STYLING: HALEY DACH