If you were thinking right about now that seemingly every celebrity—and his mother—has caught Project Runway fever, you’d be right. The story usually goes: Celebrity has zero design background. Celebrity is approached by investors to slap his name on a clothing label executed by a team of designers. And said celebrity is dubbed over night a celebrity/designer.

Andre Benjamin is all too familiar with that scenario. Years ago, the entertainer— more widely known as one half of the hip-hop duo OutKast—signed a licensing deal with investors to launch an OutKastclothing line, which made a chunk of change, but admittedly had little to do with Benjamin’s vision. “I learned quickly that unless you’re putting the money up for it, your sign-off doesn’t mean anything because they send you things a day after it’s too late to change anything,” Benjamin recalls. “I knew from that point on, I wanted to make clothes that I could really stand behind and understand.”

A style icon in his own right, Benjamin has since recently launched his namesake menswear line, Benjamin Bixby, a moniker referencing Benjamin’s fashion design alter ego, and a deliberate departure from his identity as a musician. The line is completely self-funded, and the rugged-meets-clean cut pieces, sketched by Benjamin himself, have clear references to 1930s collegiate prep. I sat down with Benjamin last night, just before 7x7’s private party hosted in his honor at Bloomingdale’s, where he put on his designer hat and let us in on some of his fashion insight.

See our slideshow from the launch event.

Tell me about your first fashion memory. What got you hooked?

I remember as a kid begging my parents and grandparents to buy these overalls. They were the thing to have in school. My grandfather got them for me and I wore them at least two to three times a week. I loved them that much. They were something different than just jeans, something extra. It’s really lame, but back then it was about having one strap buckled and the other unbuckled. Terrible!

What about 1930s-era fashion and the whole varsity football look inspired you?

Pictures. The fit. The simplistic make of the clothes. It really wasn’t about fashion. When it comes to Benjamin Bixby, we’re not high fashion. I don’t really know the cool designers. I stick to what I like. The ’30s were about function. And they made it stylish.

Was it daunting to start a clothing line amidst a sea of other celebrity clothing lines?

Yes! Because every celebrity is setting up a clothing company, it’s going to have to come down to companies and people on the outside that feel that this is a legit brand. It’ll take a smarter customer to know this isn’t just something someone put his name on. ... I like clothes and I wanted that to be the focus first. And then I hope like hell we make money off of it, so we can continue to make clothes! That’s second. But it’ll always be a challenge until people don’t associate an entertainer with Benjamin Bixby.

What do you find in common between creating clothing and creating music?

Mood. You write certain songs based on the mood you’re in. It’s the same thing with clothes. I like to judge mood by colors. You can be in a brown, a grey and a deep blue kind of mood. Or you can be in a bright pink, kind of goldish saffron kind of mood.

Last thing you were listening to when you were designing?

Steely Dan. I have a play list of my favorite Steely Dan songs, which we were listening to while designing the fall ’09 collection a few weeks ago.

What’s one thing that surprised you about starting your own line?

The timeline. In music, if I have an idea about something, I can go to a studio tonight and record it. In the clothing industry, if I have an idea for a shirt, I can draw it out tonight, but even if I had a factory to go to tonight, it would take time for them to do it. It would take time for them to send it back. …So many hands that go into it; it takes a long time to do simple things.

What’s your advice to the average guy for boosting his style quotient?

It comes down to what you’re comfortable in. For a man, it comes down to the way it fits and the colors that work with his skin color. And his body type and size. Every man can’t wear the same thing another guy can wear. .... Once you find that comfort zone you can play with things that make it your own fingerprint. The way you do your jacket. The way you do your collar. The way you roll your sleeves up. How big your cuff is. Those details make it your own.

What can we expect next from Benjamin Bixby? Will you be designing for women?

Definitely. But the focus right now is Benjamin Bixby the man’s side. And with that we will go into women’s. We’ve had some inquiries from women about things they want to wear and wish were in their size. So we’re just happy and excited about that. I like it!