A Pair of Khakis That Lasted A Lifetime

By Bill Thomas

Bill Thomas is the entrepreneur who founded Bills Khakis in 1990 and PennBilt in 2022.  It all started with a pair of original WWII khakis that Bill found at an army surplus store down the road from his college. Today, PennBilt is a continuation of a life’s work, blending the best of old and new.

I didn’t get to know my father well enough. At 10, I was aware he was a little older than the other dads. I also knew he was a bit of a character. There was this time when he piled our baseball team into his boat and towed us across town for a game. He distributed orange life preservers and hockey helmets and told us to stay low under the bow. It was the 70s.

He was a Bowdoin man from Boston who moved to Pennsylvania after the war to run a regional Aetna insurance office. He was more of the boarding school history teacher type.

I would have loved to have known him as an adult. In his absence, I gravitated to anything that built a connection to him and his times. Which explains why a pair of WWII khakis I found at an Army surplus store near my college captured my attention. The discovery turned into Bills Khakis, a-trunk-of-the-car start-up that occupied the next 30 years of my life. My early days in the khaki business were spent celebrating Americana and the virtues of my father’s generation through a pair of tan pants. The tag line read “We made Bills better by not Changing a Thing.”

In 2018, I had the opportunity to revive one of America’s oldest brands, Duck Head (you may have heard of it). If you’re over 50, and went to school in the South, there’s a good chance you grew up in “Duck Heads.” You wore them to class, frat parties, football games, church, job interviews, and a few transgressions you’d rather forget.

The assignment to resurrect Duck Head came with warning flags. To most, Duck Head stoked fond memories. However, ownership changes, discounting, and false re-starts made any effort to revive the brand especially challenging. I worked at Duck Head for a number of years until the beginning of the pandemic.

We all evolve throughout the years. Even your haircut in the yearbook looked good at the time. Change gets harder as you get older, especially if you are a traditionalist who feels obligated to stand your ground. Maybe that explains why many of us dig in our heels when trying anything new. Over time, saying “no” becomes a reflex. If you’re not careful, those Alden’s of yours can become cement shoes.

About five years ago, I saw a clear need for something new in khakis as the market was flooded with 5-Pocket “jean style” chinos. Many were made from stretchy synthetic fibers I could not identify or identify with. When your 21 year old son won’t wear 5-Pocket chinos because he doesn’t want to dress like a 55 year old, you know the timing is right to start again. It was important to tweak the original formula, while sticking to core ideals.

Forty years ago, I looked to the past before moving forward. I did the same thing with PennBilt. I describe PennBilt as “The New Authentic” – a faithful evolution of an American original that blends the best of old and new. The brand evokes mid-20th-century vibes while the product is built to 21st-century standards. We have khakis that are traditional in cut and style, made in America from 100% 8.5 oz. cotton military twill, and we also offer more modern fits and fabrications. They are all built with the care and attention to detail of that pair of original Bills khakis I developed long ago.

As a product designer, I’m energized by the challenge of staying relevant without compromising who I am. The term “updated traditional” is filled with contradiction, like opposing forces of a magnetic field. But at PennBilt, we believe you’ll find that this phrase describes our products perfectly: comfortable khakis that look great, wear well, and can last a lifetime.