A novice on the music scene, Janelle was spotted attending the Boost Mobile RockCorps ATL Reward Concert debuting her soon-to-be signature preppy tuxedo style. She opted for black blazer, red polka dot puss and bow blouse, white shorts and plaid riding boots.
Monae wore a fitted white button-down shirt, black oversized bow-tie and black slacks to her performance at the CMJ Music Marathon in New York City.
At the 4th Annual Black Girls Rock! Awards, the singer updated her signature tuxedo look by choosing a black suit featuring satin blazer lapels and satin lining alongside the trousers. She topped it off with a black oversized bowtie and black-and-white oxfords.
Mixing things up on the Glamour Magazine 2010 Women of the Year Gala red carpet, Monae debuted an all-black tuxedo ensemble with a black cape.
Monae looked like a glam rock star at the 53rd Annual Grammy Awards in a sparkling black fitted tuxedo paired with a crisp white button-down shirt, a thin ribbon tie and fitted satin trousers.
At the 2012 Met Gala, the singer ditched her classic tuxedo look for a sleek black satin sleeveless jumpsuit with crystal accents. She completed her look with crystal chandelier earrings and minimal accessories.
Channeling matador chic at the 55th Annual Grammy Awards, the songstress donned an embellished three-piece suit accessorized with a flat top hat.
At the 2013 BET Awards, Monae stunned in a monochromatic stark white Dolce & Gabbana pantsuit topped off with an extravagant crystal chocker necklace and silver Jimmy Choo Sandals.
Janelle Monae wore a floor-length embroidered red and black Tadashi Shoji cape over a white turtleneck and black trousers, with strappy black Jimmy Choo sandals to the 2014 Met Gala.
Monae opted for a cute and flirty white shirtdress for the 18th Annual Hollywood Film Awards. She tied her look together with a black flat top hat, pair of strappy sandals and a black-and-white checkered box clutch.
The singer looked regal at the 2015 CFDA Fashion Awards in a white Tadashi Shoji cape dress, covered in beautiful gold embroidery. She paired her dress with a gold T-strap Christian Louboutin sandals and a pearlized Edie Parker evening clutch.
At the Chanel Spring/Summer 2016 show, Monae donned a remixed little black dress by the brand. The dress featured a white tulle paneling down the center, a black bowtie and a crystal-encrusted belt.
Never one to shy from bold prints, Monae rocked a black and white geometric print Manning Cartell two-piece ensemble at the 2015 premiere of "Creed". She finished off her retro looks with a wide-brimmed black hat and graphic clutch.
The singer got all dolled up in a black-and-whited beaded floral Giambattista Valli Couture frock for the 38th Annual Kennedy Center Honors Gala.
Monae looked smoking hot at the 2016 Billboard Power 100 Celebration dressed in a incredibly chic red satin Cristiano Burani pantsuit. Giving her look an extra pop she accessorized with a colorful Les Petits Joueurs lego clutch and red Paul Andrew caged sandals.
While attending the premiere of "Moonlight" at the New York Film Festival, the up-and-coming actress channeled Parisian chic as she donned a cream, red and black stripped Vionnet two-piece ensemble. She completed her look with a red beret and matching Brain Atwood clutch bag.
For a New York screening of "Hidden Figures," the budding actress suited up in a metallic silver and black printed Prabal Gurung pantsuit.
All eyes were on Janelle Monae at the 22nd Annual Critics Choice Awards, when she arrived in a black and white harlequin-print Nicci Hou long sleeved ball gown. The gown featured a thigh high spilt that gave a peek to her incredibly toned legs.
The actress and singer showed her ultra-feminine side with a sleeveless, black-and-white Lela Rose top and matching flared maxi skirt at the Variety's celebration of '10 Directors To Watch' and Creative Impact Awards. She completed her look with a black T-strap Christian Louboutin pumps.
At the 28th Annual Palm Springs International Film Festival Film Awards, Monae stood out on the red carpet in a black-and-white Jenny Packham lattice gown accessorized with a stripped hard-case Jimmy Choo clutch.
Janelle Monae wowed in custom Armani to the 74th Annual Golden Globe Awards at The Beverly Hilton Hotel on January 8, 2017 in Beverly Hills, California.
Janelle Monáe in Carolina Herrera at the 28th annual Producers' Guild Awards in Beverly Hills, California, January 2017.
Janelle Monae in Chanel at the 2017 SAG Awards.