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.”

Issa Rae
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.

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

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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.

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