Chicago Fashion Week 2026: Black Designers, Big Fashion Energy & Why You Should Pay Attention

Okay, Chicago, I see you!

Chicago Fashion Week 2026 is coming, and this year I'm looking at it from a different perspective. I'm not a fashion expert. I'm not somebody who grew up knowing the difference between every designer, fabric and silhouette. I'm learning fashion from scratch—and honestly, that's what makes this interesting.

Because you don't have to be a fashion insider to appreciate a good outfit.

Sometimes you just see somebody walk into a room and think, "Okayyyyy, now THAT is a look!"

Chicago Fashion Week runs October 8–18, 2026, and the schedule includes runway shows, presentations, fashion experiences and events throughout the city. But one thing that caught my attention is the opportunity to see Black designers and creatives bringing their own perspective to Chicago fashion.

And baby, Chicago has plenty to say.

Black Fashion Is More Than Just Clothes

When I started looking into Black designers in Chicago, one thing became clear: there isn't one definition of Black fashion.

You've got streetwear.

You've got luxury.

You've got African-inspired designs.

You've got custom clothing.

You've got people mixing sneakers with tailored jackets.

You've got somebody wearing a vintage coat that looks like it came straight out of somebody's grandmother's closet—and somehow they're making it look expensive!

That's what makes fashion fun.

It's personal.

It's cultural.

And sometimes it's completely ridiculous—but in a GOOD way.

One of the events that really stands out is The Journey: An Immersive Runway Experience, presented by Emergent Fashion Society on October 14. The event celebrates Black creativity and combines fashion with music, movement and storytelling. Tickets have been listed from $20 to $60.

Now THAT is the kind of fashion event I can understand.

Don't just put people on a runway.

Give me a story!

Sheila Rashid Is Bringing Chicago Style

Let's start with Sheila Rashid.

If you've been paying attention to Chicago fashion, you've probably heard her name.

Rashid is known for combining streetwear with more tailored fashion. Her work has been worn by celebrities, including Chance the Rapper and Zendaya.

But what interests me isn't just the celebrity connection.

It's the Chicago connection.

Her clothing has that feeling of being fashionable without looking like you're trying desperately to prove you're fashionable.

You know what I mean?

Sometimes somebody has on a $3,000 outfit and you're thinking, "Okay...but why?"

Then somebody else walks in wearing a jacket, pants and sneakers and somehow looks better.

That's style.

Jennifer Akese-Burney Brings Color

Then we have Jennifer Akese-Burney of Akese Stylelines.

Her designs incorporate vibrant colors, prints and influences connected to Ghanaian and African fashion traditions.

And I love seeing that because fashion can tell you where somebody comes from without them having to say a word.

The colors.

The patterns.

The fabrics.

The shapes.

It's almost like wearing a story.

Her work was also featured in the Field Museum's Connecting Threads: Africa Fashion in Chicago exhibition, which highlighted the connections between African fashion traditions and Chicago's creative community.

That's important because African fashion isn't one single thing.

There are so many cultures and traditions that influence what we see today.

And Chicago designers are taking those influences and creating something contemporary.

Olivia Ogbara and Chicago's African Fashion Story

Olivia Ogbara is another Chicago-based designer connected to the city's African fashion community.

Her work was also represented through the Connecting Threads exhibition.

And this is where I think Chicago gets interesting.

We don't necessarily have to copy New York.

We don't have to copy Los Angeles.

Chicago can have its own fashion identity.

Actually, Chicago SHOULD have its own fashion identity.

We have the neighborhoods.

We have the history.

We have the music.

We have the art.

We have the attitude.

Put all of that together and you've got fashion.

Stephane St. Jaymes

Stephane St. Jaymes is another designer whose work has been connected with Chicago's African fashion scene and the Connecting Threads exhibition.

And looking at these designers together shows something important: Black fashion in Chicago isn't one particular aesthetic.

That's probably my biggest takeaway.

One designer can be giving you streetwear.

Another can be giving you African-inspired fashion.

Another can be giving you something completely different.

That's not a problem.

That's the point.

Robert Earl Paige

Robert Earl Paige is another Chicago designer represented in the Connecting Threads exhibition.

His inclusion is another reminder that Chicago has a history of Black creativity that deserves attention.

And fashion isn't just about celebrities wearing designer clothes.

It's also about the people creating those clothes.

The designers.

The tailors.

The stylists.

The models.

The photographers.

The makeup artists.

The hair stylists.

The people working backstage.

Everybody contributes to the fashion experience.

My Review: Is Chicago Fashion Week Worth Checking Out?

So here's my honest beginner's review.

I'm interested.

What I like about Chicago Fashion Week is that it doesn't appear to be only about people who already know everything about fashion.

There are different types of events, different price points and different creative experiences.

That's important.

Because if I'm spending my money to attend an event, I want to feel like I'm getting an EXPERIENCE.

I don't want to sit there for two hours wondering what everybody is wearing and whether I'm supposed to understand why somebody has a giant piece of fabric hanging from their shoulder.

Give me some context!

Tell me the story.

Let me experience the music.

Let me see the designer's personality.

Let me understand what I'm looking at.

That's what makes fashion entertaining.

And What Am I Wearing?

Now let's talk about the most important question.

What am I wearing?

Because I may be learning fashion, but I'm still going to show up looking like I belong somewhere!

For a Chicago fashion event, I'd keep it simple but intentional.

Maybe black pants.

A crisp white shirt.

A stylish jacket.

Some good sneakers or shoes.

And one accessory that says, "I didn't just throw this on."

That's the trick.

You don't necessarily need an expensive wardrobe.

You need an outfit that looks like you thought about it.

And please don't be afraid to wear black.

Black is timeless.

Black can be sexy.

Black can be dramatic.

Black can say, "I came here to watch the fashion show, but I'm also available for the after-party."

Final Thoughts

Chicago Fashion Week 2026 gives Chicagoans an opportunity to explore fashion from different perspectives, and the Black designers and creatives connected to these events make the experience even more interesting.

For me, the biggest lesson is that you don't have to be a fashion expert to participate.

You can be learning.

You can be curious.

You can show up with your phone and take pictures.

You can discover a designer you've never heard of.

You can meet other people who love fashion.

And you can walk away thinking, "Okay, maybe I need to upgrade my wardrobe."

That's where I'm at.

I'm learning fashion from scratch, and Chicago Fashion Week might just be my classroom.

So if you're thinking about going, don't automatically assume it's not for you because you're not a fashion professional.

You might be surprised.

And who knows?

You might walk into a runway show thinking you're just going to watch...

…and walk out ready to start your own fashion blog.

CTA: Are you planning to attend Chicago Fashion Week 2026? Which designer or fashion event has caught your attention? And most importantly—WHAT ARE YOU WEARING? Tell me in the comments!