Pendleton Woll Shirt 540

Pendleton Men’s Plaid Wool Shirt

The history of the Men’s Wool Plaid Shirt dates back almost as far as the history of the Pendleton Company itself. This all wool flannel shirt in plaid has certainly been the hallmark of the company since the 1930s. Today, we want to take a close look at the history of this famous Plaid Shirt as well as the Pendleton Woolen Mills Company of Portland, Oregon.

Thomas L. Kay

Thomas L. Kay

History of Pendleton Woolen Mills

Thomas L. Kay Mills

The roots of Pendleton Wollen Mills date back to the year 1863, when the British immigrant and weaver Thomas L. Kay settled in Oregon. After working a few years as an employee of another mill, he decided to start his own business in the wool trade, the Thomas Kay Woolen Mill in Salem, Oregon. In 1876, Kay’s daughter Fannie became his assistant and when she married the retail merchant C.P. Bishop, things changed for the better. Kay helped them to expand their business from the manufacturing side into the retail business.

Thomas L. Kay Mill

Thomas L. Kay Mill

36 years after Thomas L. Kay came to Oregon, and 9 years after his death, the family business was moved to Pendleton, Oregon in 1909 where the family took over the defunct Pendleton Woolen Mills. Strategically, it was wise to move to this northeastern part of the state because sheep were raised locally, cutting down on the transportation costs in wool production significantly.

The Pendleton Wollen Mills

Initially, the original Pendleton Wollen Mill was established in 1893 as a wool scouring plant where raw wool prepared for textile mills. Beginning in 1896, they also manufactured Native-American blankets for the Cayuse, Umatilla, and Walla Walla tribes. When the Bishop family resumed business in 1909, they revived the blanket business by introducing new designs and colors.

Subsequently, Pendleton Wool Mills expanded their product portfolio to offer woolen clothing and hence opened a new woolen mill nearby.

Pendleton Men’s Wool Plaid Shirt

Pendlton Wool Plaid Shirt 1940's

Pendlton Wool Plaid Shirt 1940’s

In 1924, Clarence Morton Bishop came up with the idea to produce men’s woolen sport shirts in bright colors and patterns. Until that point, woolen shirts had been only used for work wear and hence they only came in plain colors. The Pendleton Plaid Shirts turned out to be a success and by 1929, Pendleton was producing an entire clothing line of woolen sportswear.

During WWII, Pendleton Woolen Mills switched to war production which meant that they mostly manufactured uniforms, blankets and clothing for soldiers, and woolen shirt production stopped completely.

Pendleton Wool Shirt 1949 Ad

Pendleton Wool Shirt 1949 Ad

In 1949, Pendleton successfully introduced a womens clothing line and by the end of the 1960s, the shirts had reached cult status. One of the reasons for the popularity of the Pendleton Plain Shirt was the singing group Pendletones, who named themselves after the wool plaid shirts they wore. Later they would change their name

Pendleton 1954 Ad

Pendleton 1954 Ad

to The Beach Boys and endorsed Pendleton shirts to young Americans.

Looking at vintage Pendleton ads from the 40s, 50s and 60s, one can clearly see that the wool plaid shirt was advertised as ”Outdoor Fashion”, ”Workwear” or ”Casual Sportswear” and as such it was intended for a huge audience. Pendleton also recognized the triumphant success of casual wear and started advertising with slogans like:

Pendleton Shirt 1959

Pendleton Shirt 1959

”What Dad wore when he was not wearing his suit”.

The Wool

Pendleton Plaid Shirts used to be made of the wool of the Umatilla sheep, which were raised in the areas surrounding Pendelton. This high quality fiber turned out to be the foundation of the plaid shirt’s success because wool was more wrinkle resistant than cotton, slightly more elastic, well insulating as well as absorbent. Although tightly woven, the shirt fabric still allowed for breathability. This was especially true for the “light” shirt but also for the heavier “medium wool.” On top of that, the soft flannel texture was stain resistant and the whole shirt was easy to clean and maintained its vibrant colors.

The Pendleton Shirt Styles

Although style, weight, colors, and patterns have changed over the last few decades, Pendleton still provides all wool Men’s Plaid Shirts for casual wear. Vintage Pendeltons are often highly sought after collector’s items today.

1930s to 1940s

The shirts back then were cut rather slim and one of the most popular shirts, the “Board Shirt,” featured two chest pockets with flaps and rounded corners. Up until the late 1940s, the pockets matched the pattern of the shirt but in the 1950s the pattern was intentionally mismatched in a 45 angle in order to create a more youthful look. In any case, Pendleton shirts were made in Oregon with wool from Oregon.

Interestingly, the labels on the shirts can help to date shirts into certain time periods. All labels will read Warranted to be a “PENDLETON” TRADEMARK REG. U.S. PAT. OFF. Pendleton Woolen Mills Pendleton, Oregon 100% Virgin Wool.

In the 1930s and 1940s, Pendelton tags did not have any sizing information on them.

1950s to 1960s

These shirts had a different pattern matching on the pockets, but they also had an additional collar lining. The shirt tags began to display the size in the bottom right corner.

1970s to 1990s

Most vintage Pendleton Plaid Shirts today were produced during this era. They can be easily identified due to the woolmark tag inside. The shirt tag itself remain unchanged until 1994, with the exception of 1992.

1994 to 2009

Shirts made during this time period do not have the yellow frame on the tag anymore and feature a different font.

2009 until today

The font on the tag was changed once again and ”TRADEMARK REG US PAT OFF ” was substituted with ”Registered Trademark.” If one looks closely, the tags are stitched on the left and right sides, rather than all the way around.

The shirt itself is no longer produced domestically, but the wool is still sourced from the US. Remarkably, the company is still family owned (6th generation) and they offer a range of so called “Vintage Fit” shirts that are tailored like they were back in the day, including the “Board Shirt”.

Pendleton for Outdoor Men

Pendleton for Outdoor Men


As you can see, over the years, styles, patterns, and even the weights of the wool fabric have changed but one thing remains: the American Wool and the Vintage Cut of these continuously popular shirts.

This article would not have been possible without the support of our reader Moritz Kickhöfen who provided us with most of the information and the pictures in the this article.

If you have a story about an interesting brand or item to share, please let us know and we will work something out!

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