The Bajan pop princess wrapped herself up in chilly NYC on Saturday (9 November) in a large black puffa coat, which featured a fur hood, and sported a pair of comfy Timberland boots.
She also stuck with the old school street wear theme of her outfit by donning an oversized FILA T-shirt, which is reminiscent of the clothing worn by rappers in the 90s, and completed her ensemble with some skinny black jeans and some large gold hoop earrings, while tying her long black hair up into high ponytail.
RiRi, 25, is in the final stages of her mammoth 'Diamonds' world tour now and will be performing five final shows in North America over the next week.
She recently took some much needed time out to fly home and celebrate her Grandad Bravo's 85th birthday with a family party at her mother's house.
While in Barbados, the songstress also hung out with her father Ronald.
She posted a sweet snap of the pair together last week and wrote the simple caption: "POP$".
The picture appears to show Rihanna doing what she does best (posing in her bikini!), while her father leans into the frame over her shoulder.
What do you think of Rihanna's old school inspired outfit? Let us know below, as the best comment each week wins £50!
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Check out some vintage Rihanna with her 'Pon De Replay' video below: