Tee Sanders: The Pride of Chicago
Tee Sanders, a Chicago native and an NAACP Image Award-winning creator, has launched a great Pride initiative, partnering with the Chicago White Sox for a limited-edition Freedom Day hat.
As a comedian and entertainer who is also a Black gay woman from the renowned South Side of Chicago, Tee Sanders is open about her journey through healing, grief, resilience, and choosing joy. She reminds her audience and followers that laughter isn’t about erasing hard moments; it’s about surviving them and expressing identity and pride with humor. A born storyteller, Tee also believes in the power of brands to do more than just sell products. A logo, a tagline, and a compelling brand narrative can and should incorporate mission, values, and identity into their design.
This collection honors two watershed moments for LGBTQ+ equality: the Stonewall Uprising in 1969 and the 2015 Supreme Court ruling on marriage equality. Tee brings intention to this piece of wearable history: The crossed bats logo represents resilience and a refusal to back down, rooted in the same South Side fighting spirit the White Sox are known for. The “I’m from da crib” side patch is her love letter to Chicago, the culture, and the people who shaped her.
The Tee Sanders x White Sox partnership is a direct extension of her life’s work: building community and amplifying voices that aren’t always heard. We caught up with Tee to find out more about it and her hometown.
Vacationer: What is the biggest myth or misconception about your hometown?
Tee Sanders: The biggest misconception about Chicago is that everybody here is obsessed with deep-dish pizza. Real Chicagoans don’t really eat deep dish like that! That’s more of a tourist thing. We’re more into thin-crust, tavern-style pizza. Give me some Italian Fiesta over deep dish any day.
If a Vacationer were coming to visit Chicago for the first time and you were hosting, what are the Top 5 things you’d take them to see?
First, I’d take them to see The Bean because you have to experience downtown Chicago at least once. Then I’d take them to the lakefront because Lake Michigan in the summer is one of the best vibes in the city. I’d probably swing through Navy Pier too — at least for the experience.
I’d also take them to my old neighborhood on the South Side so they could really see where I’m from and understand the heart of the city beyond the tourist spots. Honestly, I’d probably take them to my grandma’s house too, because family is such a huge part of Chicago culture for me.
And of course, we’re eating. We’re definitely going to Harold’s Chicken because that’s a Chicago staple. Then we’re hitting Kale My Name because it’s some of the best vegan food in the city.
Please describe the queer scene for women and non-binary folks in Chicago. Are there good bars, parties, and hangouts we should have on our radar?
The queer scene for women and non-binary folks in Chicago is definitely growing and evolving. There are some amazing promoters and organizers creating spaces that feel welcoming, safe, and fun. One person really helping push that forward is Clarissa Flores with Level Sporting Club, which has become an important space for queer women and community-centered nightlife in Chicago.
Chicago has always had queer culture, but now it feels like more people are intentionally building spaces that go beyond just partying — spaces where people can genuinely connect, feel represented, and feel safe being themselves. We still need more spaces and more consistency, but the scene is definitely on the rise.
As a Black gay woman from the South Side, please explain your loyalty to the White Sox!
My loyalty to the White Sox is the same loyalty I have to the Bears, Bulls, Blackhawks, and Chicago Sky — I ride for Chicago teams, period. I’m from the South Side, so the White Sox are part of the culture I grew up around.
Not too many people from my side are repping the Cubs, and honestly, when I’m out of town, I’m representing Chicago all day, every day. That pride never leaves me.
Why is Pride Night so important?
Pride Night is important because representation matters. It creates a space where LGBTQ+ people can feel seen, celebrated, and safe. It’s especially meaningful when it happens in spaces like professional sports because for a long time, those environments didn’t always feel inclusive.
To now have Pride openly acknowledged and celebrated in those spaces shows progress. It reminds people that we belong everywhere too.
What was the ah-ha, let’s do this moment for you to create the Freedom Day ball cap?
The idea behind the Freedom Day ball cap came from wanting to create something that represented pride, culture, and freedom in a way that felt authentic to me. I wanted something people could wear that sparked conversation but also represented unity and identity.
The “ah-ha” moment was realizing fashion and merchandise can be more than style — it can also be storytelling and representation.
What are your other passion projects and hustles?
Stand-up comedy is always first. Creating is really a part of everything I do. I’ve written a children’s book that I’m hoping to publish within the next year or two. I also created a cooking game show concept because I love food, music, competition, and making people laugh.
Honestly, anything involving creativity, music, culture, entertainment, and fun — I’m interested in it.
What dream destinations are on your travel bucket list? And why?
Santorini, Greece is definitely high on my bucket list because every picture I see looks unreal. It just seems peaceful, beautiful, and like one of those places you have to experience in person at least once.
Another place is Colorado Springs. I know that one sounds random compared to Greece, but it’s always looked beautiful to me on TV and online. I love scenery and places that feel calming and inspiring.
Anything you’d like to add or share about what you have coming up over the Summer and Pride season?
This summer, my main focus is my Funny Offline Tour, which kicks off in late June or early July. I’m really excited to connect with audiences in person and continue to grow as a comedian and entertainer.
I also have film projects and other creative work coming out, but right now the tour is the biggest thing on my mind. I’m excited for the summer, Pride season, and everything ahead.
The Freedom Day hats are still available, and you can only get them by grabbing a ticket for Chicago White Sox Pride Night on June 10th at Rate Field.
Plan your trip to Chicago here.
