The image, which was first shared to Instagram on Sunday, shows the president's 16-year-old daughter adjusting her hair while wearing a t-shirt for Pro Era, a hip hop collective based in Brooklyn, New York.
After the photo emerged, Pro Era apparently saw it as a marketing opportunity and promptly shared the image to their own Instagram page with the caption: 'Malia Obama rocking that classic Pro Era tee! | Make sure you get your official Pro Era gear from theproera.com!'
Mystery surrounds the photograph - a rare private image of the teenager - and questions remain over where she took the image and how it ended up on Instagram.
A representative for Joey Bada$$, one of the founding members of the collective, told Gawker that they received the image via 'a mutual friend of Malia and the pro era member'.
Pro Era, also known as Progressive Era, formed in Brooklyn in 2009. It is made up of 47 members - including rappers, producers and non-musical members, such as photographers and publicists.
Joey Bada$$, who has previously released tapes to critical acclaim, releases his highly-anticipated debut album 'B4.DA.$$' on January 20.
But not all his publicity recently has been quite so positive as Malia's support On Friday night, he was arrested and charged with assault for punching a security guard in the face after the man asked to see his credentials before a show in Australia, ABC.net.au reported.
Joey, who broke the man's nose in the attack at the Falls Festival near Byron Bay, was granted bail and is due back in court in March.
Joey Bada$$'s debut mixtape '1999' was nominated at the BET Hip Hop Awards in 2012, and he was nominated for 'Rookie of the Year' the following year.
Some Instagram users expressed their shock at the collective's support from Malia, while others questioned whether or not the image really showed the first daughter.
Malia previously revealed she is a rap fan as she attended the 2014 Lollapalooza festival, where she was seen dancing to Chance The Rapper's set.
She was snapped at the event surrounded by burly Secret Service agents - but at least one teenager managed to sneak past them to pose for a photograph with the first daughter.
Malia also revealed herself as a selfie fan early in 2013 when she and her sister were pictured snapping numerous photos of themselves during their father's inauguration.
But the White House is famously strict about which images of the Obama girls appear in public, and the Obamas themselves said they were apprehensive about Malia having her first cell phone.
Malia was allowed a cellphone when she was 12, but was initially only allowed to use it on the weekends, her parents said.
During an interview on Live! with Kelly in 2012, Mrs Obama revealed that she 'scared the heck' out of Malia with 'days of lectures' on the dangers of talking to strangers before handing the device over.
Even then the phone was restricted to certain numbers and every person on her contacts list had to be screened to make sure they were not a threat, she said.
Malia and her younger sister Sasha are banned from using Facebook until they are 17, she added.
