[5 minute read]
The Tour de France started this week and I saw a headline questioning why Tadej Pogacar (the best cyclist on the planet) and Mathieu van der Poel were racing in $300K Richard Mille RM 67-02 watches.
Tadej, Mathieu, and other celeb athletes fall into the luxury watch-wearing category I call PROs — they wear fancy watches because they’re paid to do so. No further questions.
But what about the rest of the guys who buy watches that cost as much as a car?
It seems like there are roughly four categories of men who rock pricey timepieces: flexers, clout chasers, style snobs, and sentimentalists.
It’s 2025, and as Sean Monahan so eloquently puts it, we’ve entered the Boom Boom Era — a cultural mood shift toward luxury, indulgence, and abundance after years of restraint and minimalism. And what better metaphor than a watch? Think Barack Obama in an Apple Watch vs. Patrick Bateman in a Rolex Datejust.
FLEXERS
Flexers are just people with a lot of dough who want you to know it. They flaunt their wealth through cars, clothes, homes, vacations, watches, etc. And across all that consumption, the common threads are usually bad taste and goofy intentions.
Flexers used to be a club of the finance class, exoctic car salesmen, and Type A entrepreneurs. But they’ve welcomed a new wave of equally kooky flexers: self-styled tech bros and crypto guys who think having money makes them powerful and sexy.
Everyone has personal style (see: Steve Jobs or Pee-wee Herman). The problem is when guys fight their natural instinct to be chill in a hoody and jeans, and instead opt for expensive clothes and accessories without the slightest clue how to wear them. Style requires self-awareness — these guys will probably never realize the joke’s on them.
Some well-supported flexers come close to selling it, but there’s always something a little off. Having a crew of handlers who know their shit and guide purchases is a smart move for a personal brand — but good style has to be personal. That’s kind of the whole point.
It’s the difference between a watch feeling like an extension of the body and a guy looking like he’s losing a wrestling match with his wrist.
A stylist can lead you to water...but they’ll also lie to you about how cool you look sipping it from a straw.
CLOUT CHASERS
Clout chasers are like flexers with one key difference — they’re not obscenely (or even moderately) wealthy — but they’re desperate to appear that way. That means spending way more than they can afford on an expensive watch or, more likely...buying a Chinese dupe.
A fake watch is the perfect calling card for these guys. They’re corny as hell and dying for attention — trying to convince people they’re successful without doing the work. And the people who fall for it are also corny AF. Square pegs finding square holes.
A watch can quietly set your intentions in life if you’re not careful. You might get exactly what you’re asking for: a loveless marriage admired by fellow clout chasers for its performative perfection, business partnerships with shady dudes who make money “the easy way,” dupe-wearing managers and new hires so insecure they’d rather party with fellow posers than try to mingle with real men, and guys on dating apps flexing their Patek-draped wrists, awkwardly hovering near their faces.
STYLE SNOBS
Here’s where it gets tricky — because having good style is actually a pretty valid reason to buy a nice watch. The problem is, the line between clout chaser and style master is razor-thin.
Style snobs are purists. They’re far from flexer-flush, and they’d commit hara-kiri before wearing a fake watch.
They know their shit, research and covet rad items, seek out rare pieces, and style them well. But the risk is looking like they’re playing dress-up or trying too hard — the two cardinal sins of good style.
Style snobs are flexing — but mainly to their peers and friends. They wish the rest of the world could understand why a 1973 BMW 2002tii is special, who designed their nondescript fit, or how hard it was to find the perfect vintage timepiece. But they’ll never give up using condescention as a cudgel.
SENTIMENTALISTS
Any guy with cash or a DH Gate account can buy a “fancy” watch. That’s not cool. Caring is cool (and sexy). Sentimentalists are the more grounded version of flexers and style snobs — passionate about history, quality, craftsmanship, family ties, classic style, and analog beauty in a digital world.
These are the same guys who obsess over their kitchen knives, their shoes, tracking down obscure car parts, and finding a partner with similar idiosyncrasies. Their friends share their taste level and interests — style becomes a friendly competition. They don’t care what a random person at a restaurant thinks, and when asked about their watch, they nod and pull their sleeve down.
Watches for sentimentalists carry significant personal meaning — they’re not signals or invitations for elevator pitches.
We all have phones in our pockets — watches are no longer a utility — they’re 100% a style choice. And that’s risky business. It’s like wearing a cowboy hat when not ranching or on horseback — the rare guy can make it look kinda hottt — but everyone else just looks sad — no matter how many teeth they’re flashing with a confident grin.
Tech bro flexers can only afford to look like fools in expensive watches because there’s a lot of money to be made in training people to compare themselves to strangers. Strangers who, by the way, also hate themselves for living performative lives. And the cycle continues.
IF IT’S NOT COOL, JUST ADD ICE!
same could be said for exotic cars. oh well, still want one.
🤌🤌🤌🤌🤌