Seun Olubodun, 28, of Northern Liberties

Hipster meets old school (as in 1600s) in a line of ultra-soft apparel.

Seun Olubodun was never into fashion. In fact, he was kind of a slob.

But when he started working at a Web design company in Old City after graduating from Temple University, Olubodun noticed that most of the people around him were pretty spiffy.

"I would walk around and notice men's fashion and I realized I didn't dress well," he said.

It took three years, a bulldog, and a chance encounter, but the former fashion maladroit ended up a trend-setter with his own apparel line called Duke & Winston.

It all started when he was shopping and struck up a conversation with one of his fellow shoppers, who turned out to be a Johnny Cupcakes employee. Olubodun learned that the Boston clothing company had been started by a college dropout selling T-shirts out of his trunk.

The story intrigued Olubodun, who liked Web design but knew it wasn't his dream job - although it was creative, it was client-driven. Olubodun, who was born in England and raised in Cheltenham, wanted something he could control from start to finish.

"My first T-shirt was the face of a dog, my bulldog, that I sketched out myself, and just bought some shirts and went to a printer in the city," Olubodun said. "I was on MySpace at the time, and I just sent something out to my friends, and in a week I'd sold out all of the shirts."

He continued working at the Web design company, but at night he came up with ideas and conducted research on T-shirt materials, printing, and branding. The name Duke & Winston is in honor of his dog (Duke) and Winston Churchill, whose nicknames included "the British bulldog."

There was lots of work to be done: Trade shows needed attending, and marketing needed attention. Eventually, Olubodun found a printer in Fishtown who would do small runs - usually about 100 shirts per design.

"[The owner] brought me in there and showed me the whole process - how to put my own labels in, folding, tagging, and bagging," Olubodun said. "It's all done pretty locally."

And he discovered Alternative Apparel, a Georgia-based T-shirt company whose material is so soft it stopped shoppers in their tracks at a recent Philadelphia Designers Market show.

"It was crazy at the Designers show - I sold like 65 shirts in two hours," he said. "I was marketing them towards men, and there were all these women, and I thought, 'Oh, this is bad.' But the women were buying them for themselves, for their boyfriends, their husbands. So I think I'm going to add some more women's items to the line."

Ranging in price from $32 to $56, Olubodun's current line includes sweats and T's in nine designs, including some with British images of real-life events. (Anything shot before 1950 is usable without copyright permission, although he found that out the hard way when he used a 1970s print of Churchill, he said.) There's the phrase "Keep Calm and Carry On," embossed on a V-neck. Another shows a William Hogarth painting of Gin Lane. And one pictures the Union Jack from the year 1600. Olubodun designs each shirt to incorporate the bulldog image in one way or another.

Most of his designs are sold at small local shows, such as the Designers Market show or the Rittenhouse Row Spring Festival. He also sells his T-shirts in eight stores, including a couple in England and the Netherlands. Locally, you can buy them at Matthew Izzo in Philadelphia and Love Illuminati in Newtown. But he keeps a stock of about 2,000 shirts in his Northern Liberties apartment.

Next up, in addition to more women's shirts, is a new line of polo shirts. Olubodun wants to develop his own T-shirt fabric, working with a company to create a blend.

Olubodun works on Duke & Winston full time, but he still takes on Web design projects to help pay the bills, since most of his money is invested in the company.

At least when he looks in the mirror these days, he sees a whole new man.

"I dress a lot better now," he said. "Now I read GQ, and I try to follow them a little bit - it's a little pretty, a little hipster. I shop at J. Crew a lot."