The Untold Story of the First-Ever Upper Peninsula Silhouette Tee

During this last week, if you’re in the Upper Peninsula, there’s a good chance you may have seen this photo circulating on Facebook.

Talk about a throwback! That photo has been around since February 2008, but only a few people have seen it until now. Seeing it myself had me reminiscing and thinking I should share some details about the origin story including this photo and the humble beginnings of Michigan’s original Upper Peninsula apparel brand.

The photo is of yours truly (formally I’m Justin Sailor, but most call me Bugsy), taken in 2008. I hadn’t seen that photo in a long, long time. Little did I know my face was being plastered all over Facebook. It turns out the photo was used in a blog post titled “29 Things People From The Upper Peninsula Have To Explain To Out-Of-Towners” (what’s known as a listicle). On top of that, it was promoted to just about everyone on Facebook who likes the Upper Peninsula.

29 Things People from the Upper Peninsula have to Explain

In a span of 36 hours no fewer than fifteen people sent messages about seeing my photo on their Facebook feed. Here is a sampling of those messages…

  • I saw your photo in the ad for the Upper Peninsula on Facebook. Pretty cool! How did that come about?? (this one is from my mom, more to come on this later)
  • You made the cover! Nice work!
  • Dude, you are everywhere!
  • You’re on Buzzfeed homie
  • Thought that character looked familiar.
  • Whatttt?
  • You see this?

It is a little awkward when you unexpectedly become the cover photo of something you didn’t know existed, especially when thousands of people see it. There is no way of knowing how many people saw the photo, but as the Official Unofficial Ambassador of the Upper Peninsula these things tend to happen. Though, some are better than others Disclaimer: I was not actually quoted in this article, but they sure made it look like I was. Now offline.

It began with an epic road trip

During September 2007 I finished a year-long 50-state road trip. I returned home to Baraga to figure out what was next in life. There were two important takeaways that inspired my focus on the Upper Peninsula.

First, without effort, I collected a t-shirt from nearly every state in the union (read more here), which inspired me to want an iconic shirt of the Upper Peninsula. I knew the exact shirt I wanted, it was simple, no text, with the outline of the Upper Peninsula. I looked near and far and it simply didn’t exist. The idea without the text was, if people knew the Upper Peninsula, they “got it” (it works nicely). If they didn’t recognize what it was, they’d ask. It was time to design the t-shirt I had wanted but couldn’t find.

Secondly, while traveling across America I was eager to learn about the hometowns of over a hundred host families. In turn, they would ask about Michigan, the Great Lakes, and the Upper Peninsula. Naturally, the further away I got from the Midwest, the less they know about my homeland. A favorite question of mine was, “Can you see across Lake Superior?”. It was a joy taking on the role of ambassador of the Upper Peninsula, so when I returned home I looked for ways to continue this role. In addition to offering apparel, I scoured any source I could to find unique Upper Peninsula content, and would begin creating a series of campaigns.

Humble beginnings

On January 6th, 2008, I purchased My mom was generous enough to contribute $100 (I’m not sure my dad even knew), and Yooper Steez was started with $536, purchasing the first batch of the Upper Peninsula Silhouette shirts. They arrived on February 22nd, 2008 and came in red, blue, black, and green with white ink.

Some cal it the Upper Peninsula logo, some call it the Upper Peninsula outline, we call it the Upper Peninsula silhouette. The uniqueness of this region, given the boundaries and the demonym of Yoopers, is one that’s unmatched in the rest of the United States.

What you see in the photo is the first-ever Yooper Steez (now U.P. Supply Co.) shirt, the Upper Peninsula silhouette series. I busted out the first medium I could find (I’m a size large now), and asked my mom to grab her camera. We did an impromptu photoshoot and the first “steez photo” was taken. The photos were originally uploaded to Flickr where they were available to anyone who stumbled across them, hence my face ending up in the advertisement above. I’m cool with it. However, it is a good time to point out Creative Commons Licenses, listicles, and clickbait for those who are new to them. Always cite your sources! So we appreciate Movoto doing that. As for the content, that’s UP for you to debate.

Further down down in the Movoto article, they include a photo from our friend Betsy with the first batch of buttons we made in 2010. I still rock the original on my laptop bag.

Upper Peninsula Buttons

Some outtakes from the 2008 photoshoot (thanks Mom!)

There were 37 photos taken in that photoshoot, here are a few others that almost made the cut. And just in case anyone else wants to use them, go for it!

Upper Peninsula Outline
Upper Peninsula Logo Shirt

The photo also brings back some Hometown Invasion Tour memories. First off, a big shout-out to my friend Molly who knitted me the awesome hat while staying in Breckenridge, CO. Secondly, those are the original 574s! As for the sunglasses, they were purchased at the Aloha Stadium Swap Meet in Honolulu.

For photography geeks like myself, here are the specs from the photo seen around the world Upper Peninsula.

CameraCanon EOS 30D
LensEF 28-90mm f/4.0-5.6 USM
Capture DateFeb 22, 2008
Capture Time16:08:39 PM
Dimensions2336 x 3504
Exposure1/500 @ f/11
Focal Length38 mm
FlashDid not fire

The adventures continue

Since 2008 we have shipped shirts to all 50 states and have had customers submit photos from all seven continents. It has been a blast to bring you the Bracket of Steez, 906 Day, Lake Superior Sharks, Yooper Singles, and The Upper Peninsula Embassy. We’ve got a long list of new products and campaigns to come.

Stay awesome out there. And let’s do all the fun things together.

It still fits today!

…just a little more snug.

Upper Peninsula Outline Tee