Clueless began with a personal struggle. While I've always enjoyed dressing well, I have next to zero ability when it comes to putting together an outfit without constantly making mistakes. Like wearing black shoes with a brown belt. Which, if you ask my wife, is just about the worst thing a person can do.

For me, there's a certain vulnerability that comes with getting dressed. I'd usually stand in my room staring at all my options and draw blanks on what goes with what. Most of the time I'd end up taking pictures of a bunch of options, or put something on and send an outfit SOS text to my wife and sister for their blessing. Then the anxious wait for them to reply, checking how much time I had left before I had to catch my train to work. If I didn't hear back in time, it became outfit Russian roulette, hoping that what I picked would eventually get approval and not disapproval. I had no way to dress with confidence on my own.

Each day, I faced real anxiety over fashion choices, feeling lost in a world where making these decisions seemed instinctual to others but perplexing to me. Exploring new clothing styles felt scary. One day, I decided to test something. I texted both my wife and sister, but also uploaded the photos to ChatGPT and asked it the same question. Then I waited to see what my wife and sister said. More often than not, ChatGPT would give the same advice, but almost instantly.

That was the spark. The results were liberating. I no longer had to wait for a reassuring text from my personal stylists. This was the moment that led to creating Clueless Clothing, an app that uses the power of AI to deliver quick and thorough outfit analyses, helping users step out with confidence and plan and generate outfits.