The 5-Minute “Ugly Outfit” Shoot That Ended Up on CTA Ads

A rushed class assignment, a reluctant outfit, and a city-wide win.

How it really happened

Back in 2008, my roommate and I styled the photoshoot look together in five minutes. We both did not like it, but we went with it anyway. The assignment was to shoot a fashion look with a busy background, so we ran to Marina City Towers in the Chicago River North neighborhood. I positioned my model fast, and then I sprinted back to submit the assignment with about an hour to spare.

Why Marina City worked

The towers are a living grid. Their repeating balconies create a strong visual rhythm, turning the city into a graphic wall. That repetition framed my model and made the styling read stronger than it was. I learned in real time how to place people so the architecture does half the storytelling.

What came next

Harrington used the image for “Design Starts Here” ad, which showed on CTA buses and trains across Chicago. Marina City Online also featured the shoot. It did not launch my career, but it proved my eye and gave me the confidence to keep going.

The missed photo

I took zero pictures of the ads in the wild. Learn from me and document your wins. Even one quick phone snap helps. I added mockups here to show how it looked in the train and on platforms.

Full circle

Harrington later closed its doors and I received a refund, which I put toward more learning. Today I am studying media so I can become a better filmmaker and entrepreneur, music, and dance. That rushed day taught me to trust speed and taste and that a clear frame can turn chaos into something memorable.

Lessons I keep

Move fast with intention. Use the city as your set. Position your model so the background works for you. Always capture behind the scenes

Sometimes the rushed version is the most powerful. Trust the moment, do the work, and let the outcome catch up.