Style Observer

How to Identify an Uptown Boy

Sunday, July 02, 2017

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An Uptown (UPT) Boy is a rare specimen of Jamaican male most frequently spotted at his other, other woman's house. He is known for his good last name and bad attitude.

His natural habitat is after-work drinks and he is known for his migration patterns to “country” on the weekend. He is exclusively seen in pack formations with other UPT Boys. He is often accompanied by a series of gadgets, yachts and other expensive accessories. He survives on a diet of rum and mama's boy pampering. Grooming is extremely important to this species. Monogamy seems to not be favoured. SO brings you the latest reporting on how to spot this unusual breed of male in the wild.

Ferragamo loafers and the family business.

The essentials of an UBT are Ferragamo loafers and a family business. He will be extremely well-groomed with his hair cut by Powys. The UPT Boy will most likely, but not exclusively, be of a lighter complexion. The backbone of the UPT Boy's wardrobe is the classic button-down. This includes: Stripe button downs. Plaid button downs. Pastel button-downs. I-just-got-a-hold-of-my-trust-fund-interest button downs. You know the type. Most Uptown Boys would have started out with the Polo variety and then matured on to a wider selection of brands. Finally, a strong swim trunks game is essential for maintaining UPT boy status. Think every colour released by Vilebrequins. Ever.


UPT Boys travel in packs. Every UPT Boy will be spotted with a group of degenerate youths with similar rum consumption levels. Supporting this is a Whatsapp group convo that would end the Jamaican economy and most marriages, were it ever made public. Every UPT Boy will have one token “downtown” friend to prove his ability to relate to the masses. Downtown friends are essential for street cred. An UPT Boy will also befriend several local celebrities in sports or music.


Uptown Boys are on a strict schedule between running Daddy's business, their mistresses, and the exclusive list of activities that they engage in with their other UPT compatriots. The main activity is rum drinking, and all other activities exist to support the main pastime. Approved pastimes include : bird shooting, cycling, cricket, football, and polo.


There is no boy without his toys. An UPT Boy will have several of the following : a)Yachts (Extra points if your boat has its own T-shirts) b) Jet Ski c) Country House ( To take all his foreign girlfriends for the weekend because he still lives with his parents in town. d) Latest technical gadget such as a drone. Plus every accessory that has ever existed for it. e) Motorbike f)Benz g) other other Benz h) Family house i) Vacation House j) Other Vacay house

Sightings on Social Media

All Uptown Boys have an expertly curated social media existence of which it is vital to let everyone know they have a better view than them. This includes pictures of : a) Little sister to let the ladies know he has a soft side. b) A view from country house with the hashtag #ilivewhereyouvacation c) A picture of him and his other UPT bros 'being brotherly'. d) A picture of him and his other UPT bros popping bottles #healthiswealth e) Random promotional party picture f) Picture of sexy imported girlfriend for the weekend. Most likely with her face not showing. g) Necessary hashtags include #familyfirst #bikelife #blessed#uptownnorbrook

The Opposite Sex

Every UPT Boy will have a designated mate of the opposite sex with status “WIFEY”. This is the woman who really runs the show, and from whom he will never be parted.

This woman is supported by the addition of several other “MATEYS”, some secret and some not-so-secret.

Questionable History

Did you have some questionable time on South Beach? Were you politely asked to not return to boarding school? Did Daddy have to get you out of jail at least one time? May you have accidentally smuggled something, somewhere, some time? Survived a family scandal? Gotten away with a quadruple cheating scandal? Congrats, you're an Uptown Boy!

Now that SO has showed you how to discern an UPT Boy, we wish you the best of luck in handling this unpredictable species.




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