She officially became a billionaire last week following the success of her Fenty Beauty brand.
The singer, 33, went braless under a Harley Davidson handkerchief top which she teamed with ripped jeans for the outing with her beau, 32.
She flashed a glimpse of her ample assets in the revealing top which she teamed with the red ripped jeans worn over checked boxers.
The beauty accessorised with a gold chain necklace, multicoloured hair band, green leather handbag and sunglasses as she stepped out in style with a slick of red lip.
Meanwhile her rapper beau looked typically edgy in black dungarees which he teamed with a white vest, black cap and silver chain.
Last week, the beauty mogul was officially proclaimed a billionaire. Forbes reported that Rihanna's net worth was a staggering $1.7 billion.
At the end of July, Diamonds singer promoted her latest business venture as she teased the imminent launch of her highly-anticipated fragrance.
In March, the superstar filed a trademark for a line of haircare products and tools, ranging from shampoo to hair glitter, under the name of Fenty Hair.
Her tentative business venture, which she has not confirmed, comes as she recently hit the brakes on her Fenty fashion line, which was launched in May 2019.
Earlier this year, LVMH said in a statement that the brand, based in Paris, would be 'put on hold' pending better conditions - a rare setback for the luxury group, which has weathered the COVID-19 pandemic better than most rivals.
Rihanna - named the richest female musician in the world in 2019 - is said to be 'sad' at the decision, but her popular Savage X Fenty lingerie line, cosmetics lines Fenty Beauty and Fenty Skin are set to continue.
Her underwear brand generates about $150million in revenue, The New York Times reported in December last year - but was not at that time profitable.
Fenty Skin had sales of $30million in under four months on its e-store, WWD reports.
Fenty Beauty reportedly generated $570million in revenue in 2018, according to Forbes.
The Diamonds singer first put out her makeup line three years ago at Sephora, racking up sales eclipsing $100million over the course of its first few weeks.
By contrast, when asked about Fenty last October, LVMH's finance chief Jean-Jacques Guiony called it 'a work in progress'.
He added: 'We are still in a launching phase, and we have to figure out exactly what is the right offer. It's not something that is easy.'
Fenty fashion's Instagram account has 1 million followers; Savage x Fenty by Rihanna has 4 million and Fenty Beauty by Rihanna 10.6 million. Fenty Skin has 852,000 followers.
Fenty - named after the Umbrella hitmaker's full name, Robyn Rihanna Fenty - was meant to build on the singer's joint cosmetics venture with LVMH, with a full range of clothing, shoes and accessories.
But the line was pricey - nearly $1,000 for a padded denim jacket and $810 for a corseted shirtdress - and failed to generate as much interest as her other lines.
LVMH and Rihanna added in a statement: 'LVMH and Rihanna reaffirm their ambition to concentrate on the growth and the long-term development of Fenty ecosystem focusing on cosmetics, skincare and lingerie.'
Savage x Fenty - the singer's underwear line - recently secured $115 million in fundraising led by private equity firm L Catterton connected to LVMH.
LVMH did not elaborate on the reasons for hitting the pause button on Fenty but after a big launch and debut collection, the brand kept a low profile and never followed up with major marketing events, even before the COVID-19 crisis.
Its Instagram page had not posted since January 1 and has not released any new clothes since November last year.
© Associated Newspapers Ltd.