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A Conversation With Issa Rae - 2025 SXSW Conference And Festival

Source: Tibrina Hobson / Getty

Issa Rae’s style always gives us something to talk about, and her recent appearance at SXSW (South by Southwest) on March 8 is evidence of that. Known for her uncanny way of telling stories that come directly from our soul – and entrepreneurial ventures for the culture – Issa didn’t just show up at the Austin-based fest.

The LA native brought style, culture, and unapologetic boldness.

Issa Rae Wears Christopher John Rogers To SXSW – And Her Fit Is Bright, Bold, & Springtime Ready

Issa owned the stage in a vibrant sleeveless midi dress by Black designer Christopher John Rogers. The bold orange and purple geometric print popped against her melanin-rich skin, serving springtime dream vibes. The midi moment also had us yearning for warmer temps! Yes, Sis!

RELATED: Taraji P. Henson Rocks Box Braids And A $1300 Christopher John Rogers Dress On Late Night TV

When it comes to the shape of the dress, the form-fitting silhouette hugged her just right. Issa oozed boss baddie vibes and we were here for it. The Barbie actress kept her accessories minimal with gold strappy from Stuart Weitzman heels – made from a luscious golden liquid metallic leather we love – and gold hoops.

Issa’s style is always intentional, and that extends to her hair. With the recent launch of her Sienna Naturals haircare line, Issa continues to showcase and celebrate natural hairstyles we love.

For SXSW, she pulled her hair back into a long, braided ponytail. The style topped off her stage look with sophistication while showing off her cheekbones and bright smile.

Keynote "A Conversation with Issa Rae"

Source: Samantha Burkardt / Getty

Issa Rae’s Fashion Continues to Evolve: She Loves Black Designers & They Love Her

From her Awkward Black Girl days to her Insecure era and now as a powerhouse producer and entrepreneur, Issa Rae’s fashion game continues to evolve. She has worked with top-tier stylists like Jason Rembert and Wouri Vice and worn Black designers like Sergio Hudson, Pyer Moss, and Off-White.

RELATED: Issa Rae Embarks On Her First-Ever Fashion Campaign With Stuart Weitzman

Issa roots for everybody Black and showcases Black talent and trend in the industry.

Christopher John Rogers is just the latest designer to add to Issa’s ever-growing list of legendary fashion moments. And since we love a good Issa style moment, let’s look at some of the other Black designers she has slayed over the years.

1. Issa Rae in Christopher John Rogers

HOORAE Presents HBO Max's "Sweet Life" Season 2 Los Angeles Premiere Source:Getty

It’s obvious that Issa Rae is a Christopher John Rogers fan. We don’t blame her! Here she wears the designer back in 2022 while attending her HOORAE Sweet Life Season 2 premiere in LA. Get into the bright colors, cool length, and pattern play.

2. Issa Rae in Sergio Hudson

74th Primetime Emmys - Arrivals Source:Getty

Issa Rae redefined sophisticated beauty at the 74th Primetime Emmys. For her red carpet moment, she chose a custom black and white sculptural gown from Sergio Hudson.

3. Issa Rae in Aliette NY

73rd Primetime Emmy Awards - Arrivals Source:Getty

Issa Rae oozed grown woman energy a the 73rd Primetime Emmy Awards in 2021. She wore a sheer and sequins silver gown with a slinky feel and body-skimming design. The dress is Aliette NY.

4. Issa Rae in Pyer Moss

2018 CFDA Fashion Awards - Arrivals Source:Getty

Issa Rae hosted the 2018 CFDA Awards and took the time to highlight Black designers while doing it. Posing on the event’s carpet she slays in a blue sequined gown from Pyer Moss. 

5. Issa Rae In Off-White

30th Annual Screen Actors Guild Awards - Arrivals Source:Getty

Issa Rae attended the 2024 Screen Actors Guild Awards in Los Angeles, Californa wearing a culture couture favorite: Off-White.

6. Issa Rae in Sergio Hudson

2018 CFDA Fashion Awards - Show Source:Getty

Issa Rae made another outfit change while hosting at the Brooklyn Museum with CFDA. This time she chose a bright lime green suit from Sergip Hudson. 

7. Issa Rae in Aliette NY

33rd Annual Producers Guild Awards - Arrivals Source:Getty

 Issa Rae attended the 33rd Annual Producers Guild Awards in jeweled green  – and it was everything. The actress-producer defined her red carpet moment wearing Aliette NY from Jason Rembert.  

8. Issa Rae in Victor Glemaud

CFDA Fashion Awards, After Party, New York, USA - 04 Jun 2018 Source:Getty

Issa Rae continues to stun as host of the CFDA Awards in this demure one-sleeve dress from Victor Glemaud. From the color blocking to the bright red and purple colors, the dress is a moment.

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