The Wolf of Wall Street
Paramount Pictures

IAN FLEMING, the renowned British author of James Bond fame, once said that a gentleman’s choice of timepiece says as much about him as his [Saville Row] suit. In some ways Fleming was right—watches aren’t just an accessory or a vehicle for telling time, but future heirlooms that tell a story. They can be wearable art or purely intended as a fashion statement. They can make first impressions, good or bad, and can be signifiers of status.

Above all else, watches can offer the world a glimpse at who you are, or the person you aspire to be.

Entertaining this possibility that watches do offer telltale signs of specific individual characteristics, Esquire breaks down the most popular watch styles and what they could say about you.

Rolex Submariner

The Steel Sports Watch  

While the Rolex Submariner is considered one of the greatest and most iconic steel sports watches of all time, buying a ‘Sub’ is a predictable, somewhat vanilla choice, no? In contrast to genuine watch enthusiasts, you’re typically a one watch brand-kind of guy—Rolex ticks all the boxes. Depending on your work setting, the Sub can give off corporate snobbery; it’s the watch you bought with your end of year bonus, a sign that you’ve “made it” despite a whole tier of middle management owning the exact same watch as you now do. As for your tastes, you’re a Bond aficionado, like your steaks medium-rare with a glass of Penfolds Bin 389 and consider Entourage the best television series ever to air—Ari Gold is who you aspire to be. Sure, you can never really go wrong with a Sub, but there’s naivety in that sentiment: just look at Cousin Greg’s first watch purchase…

Carter Tank Louis Cartier

The Dress Watch

You like beautiful things and aren’t ashamed, either (are you a Taurus?) While you might be invested in the history and provenance of such beautiful pieces like a high-end dress watch, it’s likely this watch was a heirloom; passed down by Dad or Grandad. You’re somewhat of a traditionalist and a believer in that what’s not broken doesn’t need fixing; sticking to familiarity is what works best for you. You’re partial to a well-tailored suit but chinos and RM’s are likely your comfort choice at weekends; cheese and wine nights get you going; and fine dining degustation experiences are high on the agenda, at least monthly.


TAG Heuer Carrera
TAG Heuer

The Chronograph Watch

So TAG Heuer was likely your first “real” watch, perhaps a graduation or milestone birthday present in the form of a Link or Aquaracer. So, for the longest time, TAG Heuer was (or is) your watch brand of choice. Naturally, you’ve progressed to knowing and coveting vintage Carreras, and the idea of owning a Chronograph—a watch function you’ll never have use for —is high on your list. In saying that, you’re an automotive freak, like your cars flashy and fast, and would love to one day own that vintage car that enables you to wear leather car gloves and a vintage chronograph strapped on your wrist.


ROLEX GMT Master Pepsi

The GMT Watch

A watch made for pilots and those who frequently the world, no watch is more synonymous with the GMT function than the Rolex GMT-Master, especially the “Pepsi” or “Batman” variants. As a GMT wearer, you’re a self-professed “traveller” that will happily enlighten those around you with your worldly experiences, whether called upon or not. You know the importance of keeping track of your home timezone when travelling—the Instagram algorithm doesn’t lie—and will be the first to tell watch enthusiasts that you bought a Rolex GMT for its function, not hype. If the latter rings true, you were happy to wait two years to collect your highly coveted Pepsi or Batman/girl.

TUDOR Black Bay 58

The Dive Watch


Let’s be honest: unless you’re a diver, no one really needs a dedicated dive watch. But hey, they look good and are practical as hell—and you think so, too. In saying that, you’re likely an adventurist that finds enjoyment in unconventional recreations: surfing, rock climbing, mountain bike riding. With a dive watch strapped to your wrist, you feel invincible knowing your watch is made for impact. You’ll know that one of the best watches of this category is the TUDOR Black Bay, and you’ll happily tell onlookers that TUDOR is, in fact, the baby brother brand of Rolex; the Black Bay 58 is as close as you can get to what Rolex “once was”. But you’re likely kidding yourself: you’d love to own a Rolex, be honest.

Richard Mille
Richard Mille

The High Complication Watch   

If you’re looking to purchase a high complication timepiece, you likely sit in one of two categories: you’ve arrived at the next stage of your watch journey, joining enthusiasts and collectors who covet such pieces. Or, you have enough money to splash and think any watch worth over $500K must be worth it; the bigger the better, right? More often than not, you’d be wrong (rap legend P. Diddy once said of Richard Mille timepieces, “I’m not a hater, I’m a connoisseur of fly shit and I’m just telling y’all, y’all getting tricked by the Richard Mille.”).

Be wary of your decision to don such timepieces; Kendall Roy adopted the Richard Mille RM 67-01 in the final season of Succession and we know how that turned out for him. Buying a watch with high complications doesn’t make you a watch god or any more important within society, so choose wisely if you’re looking to drop some dosh on your next watch purchase (and be ready to back up your watch knowledge when quizzed by the mass of watch faithfuls who will comment on your Instagram posts).

Omega x Swatch MoonSwatch

The Quartz Watch   

Quartz schmuartz, you don’t really see the big deal between a quartz-run watch and a mechanical watch; as long as it keeps time and is of the current watch zeitgeist, that’s fine by you. Take the recent Omega x Swatch ‘MoonSwatch’ collaboration, for example. While not necessarily a watch enthusiast, your sense of FOMO was triggered when the world went crazy for the $350 plastic watch—you wanted in! And you got lucky, because lining up at 4am at your local Swatch store is what needed to be done. You’re not generally a stickler for the traditional, so a dash of colour and pattern doesn’t phase you (you likely went for the Mission to Pluto, right?).

Apple Watch Ultra

The Smartwatch 

So you’re a man of priority, and dropping thousands on a new watch just isn’t on your list right now. But, in order to meet your goals and be the best version of yourself, you have to stick to time… and a regime. Enter, the smartwatch. More than a watch, this ‘tool’ needs to be functional beyond telling time—how else can you track your marathon progress as well as your chicken roasts? On the topic of workouts, you need your sessions to be precise and efficient, something a smartwatch can help you do—God forbid you don’t hit your daily steps for the day! You’re pretty clueless when it comes to watches, and probably don’t know the difference between the aforementioned quartz and mechanical variants—aren’t all watches chargeable?


Is this the best Cartier release of 2023?

When it comes to watches, Paul Wesley isn’t playing around

Watches in sport: 6 of the best timepieces worn by athletes