Find more stories on luxury and wealth Not just a dress watch, or a sports watch, but one that could be all things to all the people, and all the settings, in your life: your mates at the pub, your boss in the boardroom, your beloved on date night. To assist with the decisions we called in a man who helps people deal with this dilemma daily, Michael Chylinski of the Watch Collector website. "Guys will come in to me and say, 'I need one good watch, one real watch, but it has to be versatile. So what do I get?'," Chylinski says. "My first piece of advice is to buy the best watch you can afford. There's a syndrome where you'll buy a watch under your budget to 'be safe', then forever be lusting after the one that was slightly more, but ultimately a better choice."

The following options are proffered with a guarantee of minimal buyer's remorse. Each model has vintage and modern alternatives, to account for both tastes. The criteria for these 'one' watches is bang for buck, recognisability on the wrist and, importantly, that they be 'hackable' – which means their personalities can be modified with different strap options. Facebook CEO Mark Zuckerberg's t-shirt theory can apply to watches, too. Credit:Bloomberg Omega Speedmaster Professional There is no need for a 'vintage' and 'latest' image here as they are one and the same: the 'Moonwatch', as it's known, has remained practically unchanged since it was worn by Buzz Aldrin when he walked on the surface of the moon in 1969. "The Speedmaster Professional as it is, is what the consumer wants," Omega president Stephen Urquhart says. "And NASA are very happy with the watch as it is, too."

Adds Chylinski: "Few watches fit in the realm of the 'Speedie' when it comes to value, quality, true icon status and, of course, its story. Nothing can hold a candle to it. "And the plexiglass and matte dial is the perfect recipe for hackability. You can wear it on a canvas NATO, a distressed leather strap or its bracelet and it will look great." Rolex Explorer My first piece of advice is to buy the best watch you can afford. Michael Chylinski Ironically, it's one of the least Rolex-looking Rolexes on the market, and yet it fits the bill.

"It's simple, it's a wristwatch from the golden '50s era, it has a matte grey dial, luminous numerals and indices and a history of adventure," Chylinski enthuses. The original Explorer was 36mm but the current model has grown in proportion to 39mm. "It's a ripper-looking watch. It'll pass as a casual watch with a hoodie at South Melbourne Market, or slip under the cuff of a shirt at a formal occasion. It's one of the most adaptable watches you can get and is dressier than a non-date Submariner, which is why it ousted it from this spot." Tudor Snowflake Submariner/Pelagos The vintage Tudor 'Snowflake' Submariner (the nickname referring to the shape of the handset) is not only a great choice in terms of its classic, adaptable style, it's also a wise investment as an affordable – well, compared to Rolex – collector piece. The updated Pelagos homage model introduced in 2012 is the ultimate wrist warrior, with a stealth, matte appearance contrasting with the current slew of dressier dive watches. Would look absolutely terrific with a tuxedo. TAG Heuer Carrera

Along with perennial favourites like the Rolex Daytona, the Carrera – first released by Heuer in 1963 – is one of the classic chronographs. "The difference between the second and third version of the Carrera is that the earlier version, which was the first production of TAG Heuer's 1887 movement, doesn't have the tachymetre or the anabolic look of the chrome edged subdials," Chylinski says. "It's clean, it's less busy and it wears really well on bracelet and leather strap." Says David Chalmers, the founder of leading TAG Heuer fan site Calibre11.com: "The second version was only made for a short time and only sold in selected countries, so they can be hard to find. But if you love the look of the Carrera 1887 and want something a little different, it's well worth trying to hunt one down." IWC Big Pilot You don't need to be a complete watch geek to pick up that there is something of a cult following for the fabled IWC Big Pilot watch, which always leaves an impression thanks to its size and simplicity. When you discover that its more famous devotees include John Malkovich, Bradley Cooper, Orlando Bloom and Jude Law, the myth only gets spicier. "It's a fantastic everyday watch and it has serious wrist presence," says Chylinski. "The huge jewel-shaped crown will start conversations and the curved lugs make it far more comfortable on the wrist than it looks. It suits a business shirt as well as it does a leather jacket."

Loading Andrew McUtchen is the founder of online watch magazine Time+Tide. Follow Executive Style