Fashion Issa Rae Continues Her Winning Style Evolution Welcome to "Who Won Fashion Today," where we award the boldest, best dressed person of the day. Winning fashion doesn't necessarily mean you're wearing the most expensive, trendiest, or prettiest dress. Rather, we reward risk-takers—those that stay true to their personal style and make us go, "Now THAT is a LEWK.” By Ruthie Friedlander Ruthie Friedlander Twitter Ruthie Friedlander is a New York-based writer, editor, and founder of the At Large Agency. She is also the co-founder of The Chain, a non-profit eating disorder support system for women in fashion and entertainment. InStyle's editorial guidelines Updated on February 24, 2017 @ 10:30AM Pin Share Tweet Email Photo: Amanda Edwards/Getty What does it take to stand out at one of the most star-studded events of the calendar year? Ask Issa Rae. The Insecure actress, who once favored leather jackets and tees, arrived to Essence's Black Women in Hollywood event yesterday in a truly glamorous gown by Francesca Miranda. One that we undoubtedly can add to our beloved Naked Dress gallery. Janelle Monáe Teaches the LBD a Lesson Rae has been on a fashion rampage since the Golden Globes thanks to her stylist, Ayana, who has put her in fitted, Hollywood-glad looks all awards season long. 16 Times Issa Rae Was the Definition of #HairGoals Frazer Harrison/Getty Image zoom 2017 Golden Globe Awards The TV star wore a regal rope twist style to this year's Golden Globe Awards. Frazer Harrison/Getty Image zoom 2017 Independent Spirit Awards Nominee Brunch Issa's accessorized do won the red carpet at this year's Independent Spirit Awards Nominee brunch. Jason LaVeris/FilmMagic Image zoom 2016 Insecure L.A. Premiere The writer and actress looked breathtaking in this hairstyle at the October 2016 premiere of Insecure in L.A. Jason LaVeris/FilmMagic Image zoom 2016 HBO Post-Emmy Awards Reception Issa Rae dons a textured up-do for the HBO Post Emmy Awards reception in September 2016. Michael Tran/FilmMagic Image zoom October 2016 Jimmy Fallon Appearance Issa Rae rocks a braided style during her interview with Jimmy Fallon in October 2016. Andrew Lipovsky/NBC Image zoom October 2017 Jimmy Fallon Appearance We need a complete 360 of this braided updo--it's fabulous. Paul Archuleta/FilmMagic Image zoom 2016 Insecure Block Party Issa Rae attends the September 2016 Insecure block party in style. Neilson Barnard/Getty Image zoom 2016 Urbanworld Film Festival Issa Rae's braided crown stunned at the Urbanworld Film Festival in September 2016. Kris Connor/FilmMagic Image zoom 2016 BronzeLens Film Festival Issa Rae's beautiful mane captured everyone's attention at the BronzeLens Film Festival in August 2016. Paras Griffin/Getty Image zoom October 2016 SirusXM Radio Studio Appearance Issa Rae's curly coils are perfection during a SiriusXM Studio appearance in October 2016. Cindy Ord/Getty Image zoom 2015 Los Angeles Film Festival Issa Rae's auburn fro looked amazing at the 2015 Los Angeles Film Festival. Alberto E. Rodriguez/WireImage Image zoom 2016 Los Angeles Film Festival Issa Rae's side braids were a major hair win at the 2016 Los Angeles Film Festival. Jerod Harris/WireImage Image zoom 2016 BET Awards Dinner Last year, Issa Rae's hair was simply fabulous at this 2015 BET Awards dinner. Jason Kempin/BET Image zoom 2017 Insecure Panel Discussion Issa Rae's perfect coif was #hairgoals at a Insecure panel discussion earlier this year. Jeff Kravitz/FilmMagic Image zoom 2014 L.A. Event Issa Rae was certainly the one to watch at this 2014 L.A. event. Jennifer Lourie/FilmMagic Image zoom 2016 Appearance Issa Rae's curls were poppin' during this 2016 appearance. Astrid Stawiarz/Getty 1 of 16 Advertisement So you win fashion today, Ms. Rae. You AND your naked dress.