By Sylvie Kirsch
Medill Reports

The 2024 Democratic National Convention in Chicago was both a political potluck and a fashion show. Keynote speakers like Michelle Obama, Oprah Winfrey and Ella Emhoff wowed viewers with chic, sleekly tailored looks that only added to the gravitas of their messaging. Democratic delegates also wore a mix of custom-made items and striking designs that helped them express their identity and, often, their support for presidential nominee Vice President Kamala Harris.

Kelly Jacobs, a Mississippi delegate and self-anointed “political fashionista,” has drawn attention for her eye-catching outfits since 2004, when she began using fashion to broadcast her ideological affiliations while circumnavigating unwarranted judgment.

“Where I live, Democrats are usually African American, and when I go in the room, they’re sure I’m a Republican – unless I’m rocking the dress,” she said.

One of Jacobs’ outfits has also been featured on the front page of the New York Times, and she donated a custom-made political-themed dress to the New-York Historical Society.

On day two of the convention, the Mississippi delegate wore a dress with a drawing by artist Rascal that instructed DNC attendees to “Storm the ballot box like they stormed the Capitol on Jan. 6,” referencing the insurrection in 2021. The message is peppered with 13 photos of Taylor Swift’s 2020 V Magazine cover – Swift’s lucky number – with the word “vote” cascading down the side in bright blue letters.

Jacobs, the volunteer campaign manager for Diane Black’s congressional run, is combining her love of Swift with political activism. During Black’s campaign, Jacobs made and distributed 2,400 Eras Tour-esque friendship bracelets; at the DNC, she handed out 1,000 more that read either “SWIFTIE VOTER” or “KAMALA.”

The back of Jacobs’ day two dress bore photos of Swift and her boyfriend, Kansas City Chiefs tight end Travis Kelce, at Swift’s London concert on June 23. Jacobs decided to customize her convention dresses in the same style as Pete Souza’s intimate photos of Barack and Michelle Obama as president and first lady.

“The reason why it’s a cute dress is because the picture is so cute,” she said. “So, for political fashion, choosing the right picture is really important.”

 

On Aug. 20, the second day of the 2024 Democratic National Convention, Kelly Jacobs showed her eagerness to vote and her love for Taylor Swift with vivid colors and a cardboard cutout of the singer’s head. (Sylvie Kirsch/MEDILL)

 

Lakeylah White, a delegate from Hattiesburg, Mississippi, was inspired by Jacobs’ custom political looks and decided to commission her own. A local Hattiesburg seamstress made her dress for the convention by sewing together two banners of a Harris poster that likened her to one of Barack Obama’s iconic 2008 campaign images.

“She inspires me, and this just symbolizes hope and our future,” White said.

The delegate paired the dress with a string of pearls in honor of Harris’s signature look and a hat from Macy’s that she customized with buttons supporting Harris and President Joe Biden. One simple pin, however, bears a favorite quote of White’s from Vernon F. Dahmer, who was killed while championing voting rights in Hattiesburg:

“If you don’t vote, you don’t count!”

 

Delegate Lakeylah White poses in her custom-made “Harris 2024” dress that she wore on Aug. 21 to the third day of the 2024 Democratic National Convention at McCormick Place in Chicago. (Sylvie Kirsch/MEDILL)

 

Angela Alsobrooks, the county executive of Prince George’s County, Maryland, and Democratic Senate candidate, delivered a speech supporting Harris on night two of the convention. She wore a custom-made suit by a friend and fellow Marylander who used to sew for the ’80s sitcom “227.” Alsobrooks knew her outfit had to match the gravitas of the occasion.

“Oh my goodness, what a special night this is,” she said. “I feel so honored to have been invited to speak here and wanted to have on something that will represent the people of my county and my state, and I think she really helped me to put my best foot forward tonight.”

 

Angela Alsobrooks wears a custom-made white skirt suit set after delivering a keynote speech on Aug. 20, during the second main session of the 2024 Democratic National Convention. (Sylvie Kirsch/MEDILL)

 

Cynthia Hohman, a delegate from Indiana – “hence the Colts shirt,” she said – donned a sparkly, patriotic mylar wig in preparation for going into the United Center on day three of the convention. “The people back home are watching, so I wanted to see if I’ll get spotted,” Hohman said.

The delegate had been waiting to sport the wig since ordering it for the 2020 Democratic National Convention in Milwaukee that was canceled due to the COVID-19 pandemic – but actually wearing it this year took some mental preparation.

“You’ve got to get your gumption up to put something like this on,” Hohman said.

 

Cynthia Hohman said she hoped family and friends watching the convention on TV would have an easier time catching a glimpse of her in this red, white and blue mylar wig. (Sylvie Kirsch/MEDILL)

 

Washington delegate Chris Porter started the convention off strong on Aug. 20 by wearing an American flag-themed outfit, complete with a “Cowboys for Harris” sash inspired by Beyonce and her song “Freedom.” The next day, Porter celebrated a different flag, decked out in rainbow Pride colors to honor LGBTQ+ trailblazers. The set was also a reference to the vice president, who is championing queer rights as a centerpiece of her presidential platform.

“The Harris campaign talks about freedom – freedom to be who you are, freedom to vote, to have housing,” he said. “And all of that just syncs so nicely as I stand on the shoulders of those who came before me.”

The delegate said incorporating blinking lights onto his hat was a purposeful choice. “I like the flash that comes with it. It makes it pop – even though I think I have on a rather poppy outfit.”

 

Washington delegate Chris Porter poses outside of the United Center on Aug. 21, after the third main session of the 2024 Democratic National Convention in Chicago. While Porter initially paired his bright rainbow vest with a matching rainbow boa, he loaned it to a friend for the evening to spread the bright, colorful energy throughout the stadium. (Sylvie Kirsch/MEDILL)

 

Charlane Oliver, a delegate and state senator from Tennessee, expressed her sisterhood with Harris and many other attendees by wearing the colors of their sorority, Alpha Kappa Alpha.

“Normally, pink and green do not go together, but anytime you see a member of Alpha Kappa Alpha, we know what that means,” she said.

She purchased spring green Ann Taylor slacks and paired them with a collared white button-down and soft pink blazer from Dillard’s. A pair of pastel fuchsia Converse and pearls were obvious additions, another call to Harris’s sophisticated political flair. Oliver said she wanted to wear a carefully curated outfit as she believed in the importance of putting one’s best foot forward.

“This is a place to make sure you feel good. It’s a place to be energized, so why not look good and feel good?” she said.

 

“I wanted to make sure I was comfortable and cute. That was the goal for this week,” Charlane Oliver said of her convention outfit, noting she was particularly proud of her pink Converse, one of Vice President Kamala Harris’s favorite footwear brands, which honored the Alpha Kappa Alpha sorority. (Sylvie Kirsch/MEDILL)

 

John Naughton, a former sportswriter and delegate from West Des Moines, Iowa, agreed green and pink make a great combination. His day three DNC outfit, which showed off one of the 30 trilby hats in his collection, was not inspired by Alpha Kappa Alpha – he was unaware they were the colors until fellow attendees began complimenting him. Instead, for Naughton, it’s more about using color theory to catch people’s attention.

“I like dressing in bright colors because people react to that in a generally positive way,” he said. “It brings a lot of positive energy, and then I get a lot of positive energy in return.”

 

John Naughton’s retirement from sportswriting coincided with the birth of his fashion journey – and a particular penchant for resplendent looks. (Sylvie Kirsch/MEDILL)

 

Delegates Samantha Herring and Savannah Atkins are a mother-daughter duo who rocked handmade bright pink blazers with lit-up pearls that read “Florida for Women” on Aug. 20 (“Pink is my color,” Herring said). The message is twofold: to amplify the voices of the 4.7 million women across the state and support the passing of Amendment 4.

The amendment, which Floridians will vote on this November, would prevent any law that prohibits, punishes, restricts or delays abortion before viability or when necessary to protect the health of the patient. This would re-enfranchise health care providers to make decisions on behalf of the parent’s health without fear of legal retribution.

“When my son and daughter were born, they had the same rights to health care,” Herring said. “Today, unfortunately, in the state of Florida, my son has stronger rights than my daughter does, and there’s just something fundamentally un-American about that.”

Atkins and Herring turned to fashion to state their support for the constitutional measure.

“I really believe in expression – whatever makes you feel confident, beautiful and capable, roll with it. For me, it’s a political message because it’s the core of my being,” Herring said. “I believe strongly in using our voices, and I believe we have a responsibility to engage civically.

 

Samantha Herring, right, and Savannah Atkins sport matching blazers celebrating Florida Democrats and hopes for the passage of state Amendment 4 at the Rural Caucus meeting on the second day of the 2024 Democratic National Convention in Chicago. (Sylvie Kirsch/MEDILL)

 

The delegates also wore matching pink nail polish dotted with the vice president’s name and cowboy hats decorated with buttons flashing lights.

“My mom and I, we’re Southern girls at heart, and we’re always having fun together with fashion,” Atkins said. “You can make a beautiful statement and look beautiful at the same time.”

 

Sylvie Kirsch is a recent graduate from Northwestern University’s Medill School of Journalism.