The singer has a simple guideline when it comes to the red carpet: “Embrace skin-baring outfits.” In light of her Video Vanguard Award at the upcoming MTV VMAs, we’ve gathered a collection of her boldest and most revealing outfits throughout her career.

Brittany Talarico is the Deputy Style Director at PEOPLE, responsible for overseeing the brand’s extensive coverage of Style and Beauty on their digital platforms. One of her key roles is taking charge of the highly popular Met Gala coverage, an event that attracts a significant audience each year on PEOPLE.com. She also conducts interviews with influential figures in the industry, including the prominent Kardashian-Jenner family, while simultaneously delivering breaking news on A-list celebrities. As a native of the Jersey Shore, it comes as no surprise that her most memorable interview to date was with the legendary Bruce Springsteen. In addition to her role at PEOPLE, Brittany frequently contributes to the People Every Day Podcast and has represented the brand on various national television programs, such as Good Morning America and two special broadcasts on the British Royals aired on The CW. She joined PEOPLE in 2013 after serving as an Associate Editor at Cosmopolitan magazine.

In an impressive display of her fashion prowess, Rih proudly embraced her role as a fashion icon while accepting the prestigious Fashion Icon Award. Her unforgettable outfit, created exclusively by Adam Selman, was a true masterpiece. The ensemble, composed of a daring fishnet dress, complemented by stylish gloves and a chic headscarf, was painstakingly adorned with an astonishing number of over 216,000 dazzling Swarovski crystals.

At the vibrant Kadooment Day event, the Barbadian beauty proudly displayed her love for her hometown with a mesmerizing costume crafted by the talented designer Lauren Austin. This stunning ensemble, complete with a peacock feathered headdress and wings, inspired by the Mockingjay, was accentuated by a dazzling crystal-encrusted bra and underwear set. Speaking about the pop star, Austin shared with Metro Caribbean blog that she is an incredibly genuine, delightful, and compassionate individual. Austin further expressed her admiration for the singer, noting how effortlessly she carries off each piece with grace and elegance, never encountering any difficulties or complaints.

Ever wondered what’s hidden from view? This stunning ensemble by Stella McCartney unveils a whole new level of chic with its captivating bare-back design. To add an extra touch of grandeur, the fashion icon herself accessorized it flawlessly with a breathtaking 116-carat Jacob & Co. diamond choker.

She transitioned from flaunting her well-toned abdominal muscles to revealing a glimpse of her buttocks in a glamorous Stella McCartney dress, adorned in gold and featuring an audaciously plunging backline.

The vocalist hardly ever chooses to wear a bra, making a gown equipped with built-in covers for her nipples an ideal choice for her wardrobe. This particular gown was designed by Tom Ford, who expressed extreme happiness when he witnessed her donning it, even going as far as writing a heartfelt tribute dedicated to her breasts.

When it comes to Rihanna’s personal fashion statement, she has a unique take on the classic casual attire of jeans and a t-shirt. For her, a vibrant yellow Alexandre Vauthier dress with a daringly high slit and low neckline is the equivalent of this everyday outfit.

Absolutely, the Jean Paul Gaultier bustier and sheer lace skirt adorned with beads definitely turned heads, but it was the Dominican doobie wrap hairstyle sported by the celebrity that caught everyone’s attention.

Rihanna expressed her admiration for the custom Armani gown, revealing that it drew inspiration from Michelle Pfeiffer’s iconic character in Scarface. The dress captivated everyone’s attention, just like the timeless allure of the film itself.

Here we go again! Rihanna looked absolutely stunning in a form-fitting, white Adam Selman dress with an open back as she accepted the Moonman award for Video of the Year, for her popular song “We Found Love.”

Let’s take a trip down memory lane and recall the unforgettable moment when Rihanna skillfully dodged a fashion mishap. She effortlessly pulled off a stunning white bridal-esque dress designed by Jean Paul Gaultier, which showcased alluring sheer panels in just the right places.

This Marchesa dress exuded a feminine charm with its delicate floral laser cutouts. However, its design broke away from convention, daring to be bolder and more expressive with its hemline and revealing bodysuit.

If you find yourself sheltered under Rihanna’s “Umbrella,” there’s no need to worry about wearing pants.

During her debut appearance at the VMAs, Rihanna left a lasting impression as a true trendsetter in the world of fashion. Defying conventional style norms, she confidently embraced a unique ensemble comprising a petite neutral-toned crop top, a dazzling sequin vest, and a stylish white denim pantsuit. To further elevate her look, she adorned herself with a captivating body chain and bedazzled sandals, showcasing her individual style and fearless approach.