Hand Painting 150 Woodford Reserve Bottles for Johnnie-O's Grand Opening in Wilmette on Chicago's North Shore

Some projects push you creatively. Some push your endurance. And every once in a while, one comes along that does both. This summer, I had the incredible opportunity to hand paint and engrave 150 custom Woodford Reserve whiskey bottles for the Johnnie-O Plaza Del Lago Grand Opening in Wilmette, Illinois just north of Chicago. It was one of the largest studio commissions I've ever completed - and without question one of the most rewarding. With less than a month to complete the project, I knew organization, consistency, and a lot of late nights were going to be the key to success. Bottle Painting in Chicago has really taken off and I am here for it.

Every finished bottle celebrated the opening of Johnnie-O's newest North Shore location.

A Tribute to the North Shore

Johnnie-O's founder grew up in the North Shore of Chicago, making the Plaza Del Lago location especially meaningful.

Rather than creating a generic design, the talented creative team at Johnnie-O developed a collection of hand-drawn illustrations inspired by the community itself.

The bottle artwork included iconic North Shore imagery such as:

• Hydrangeas

• Martini glasses

• Rocks glasses

• The commuter train

• A sport coat

• And other sketches unique to the North Shore of Chicago

Every bottle told the story of the neighborhood and served as a keepsake celebrating the store's opening.

Natural light really brought the engraved lettering and painted illustrations to life. Each of these icons represents a part of the North Shore of Chicago and makes the bottle that much more unique.

Less Than One Month to Paint 150 Bottles

When I accepted the project, I knew there wasn't much room for error. Between travel, live events, and other client work, I had just a few weeks to complete 150 fully hand-painted and engraved bottles before the grand opening. From the very beginning, staying organized became just as important as painting itself.

The First Step: Sourcing 150 Woodford Reserve Bottles

The project began with sourcing all of the bottles. Fortunately, Shelby at my local Hy-Vee liquor store went above and beyond to help coordinate the order. She made the entire process incredibly smooth, and I couldn't have completed a project of this size without her help. She even gave us a discount, saving the client quite a bit of money and that is always a plus. Once the bottles arrived, I got to work immediately.

Watching the rows of bottles grow was one of the most satisfying parts of the project.

Developing the Process

Like many large commissions, the first few pieces were all about refining the workflow.

Initially, I transferred every illustration using white carbon paper, carefully tracing each individual icon onto the glass before painting over it with DecoArt paint markers.

After about twenty bottles...Something changed. The designs had become so familiar that I no longer needed the transfer paper. I began painting each icon completely freehand. That moment felt like crossing a milestone in the project.

Each bottle was personalized with hand engraved calligraphy reading "Johnnie-O Plaza Del Lago – August 1, 2026."

Every Bottle Started the Same Way

To ensure consistency across all 150 bottles, I followed the exact same process every time. First, I used a white Stabilo pencil to establish perfectly straight guidelines for engraving on the bottle. Next, I hand-lettered: Johnnie-O Plaza Del Lago August 1, 2026

and then hand engraved every bottle before filling the lettering with silver Rub 'n Buff, allowing the personalization to stand out beautifully against the whiskey.

Only after the engraving was complete did I begin painting. One icon at a time.

Until the entire bottle came to life.

After the first twenty bottles, I no longer needed transfer paper and began painting each illustration completely freehand.

Finding My Rhythm

At the beginning of the project, each bottle took me roughly one hour to complete.

By the end...I had cut that time nearly in half. After painting the same illustrations hundreds of times, my hand naturally found its rhythm, and I was consistently completing each bottle in around 30 minutes. It was amazing to see how much efficiency comes simply from repetition and experience.

The finished design featured custom North Shore-inspired illustrations created by the Johnnie-O creative team and painted completely by hand.

Staying Organized

One of the biggest lessons from this project was that organization matters just as much as artistic skill. Rather than working randomly, I completed the bottles one case at a time.

Working in batches of twelve allowed me to know exactly:

• How many bottles were complete

• Which bottles still needed engraving

• Which boxes still needed painting

• Which bottles had already been quality checked

Every completed box received a label. After each bottle was cleaned, inspected, and wiped down, I added a final check mark before sealing the case. By the end of the project, the system practically managed itself.

Organization was everything. Each case was labeled, completed, quality checked, and tracked throughout production.

Delivery Day

The day before the grand opening, I carefully loaded every case into my vehicle and made the drive from Iowa to Wilmette, Illinois on the North Shore of Chicago just north of the city. There's always a little anxiety transporting that much work.

Weeks of painting...

Thousands of brush strokes...

Hundreds of hours...

All riding in the back of my car.

Thankfully, everything arrived safely.

The final step: loading all 150 bottles and making the drive from Iowa to Wilmette for the grand opening.

Seeing the Client's Reaction

Watching the Johnnie-O team open the boxes made every late night worth it.

They were absolutely thrilled. Hearing how happy everyone was with the finished bottles after putting so much care into each one was incredibly rewarding. As artists, we spend so much time focused on getting every detail right that we rarely pause to appreciate what we've accomplished until someone else sees it for the first time.

The beautiful new Johnnie-O Plaza Del Lago location where guests enjoyed complimentary live engraved Woodford Reserve bottles during the grand opening celebration.

Painting Live at the Grand Opening

Although all 150 bottles had already been completed, we intentionally left a handful unfinished. During the grand opening, I completed four bottles live so guests could watch the painting process firsthand. It became one of the highlights of the evening.

One comment I heard over and over again was:

"Wait...these are actually painted by hand?"

Guests couldn't believe one person had painted all 150 bottles. Watching people examine the tiny illustrations up close and realize they weren't printed—but individually painted—was incredibly rewarding. I also had so many people thank me for my time and for my talent and while you might think that is normal, it most definitely isn't and was so nice to hear.

My engraving station was set up inside the new store, allowing guests to watch each bottle come to life.

Why Live Bottle Painting Creates Such a Memorable Experience

Whether completed ahead of an event or demonstrated live, bottle painting combines craftsmanship, storytelling, and personalization in a way few event activations can.

Luxury spirits brands, retailers, and corporate clients love creating exclusive keepsakes that guests can't purchase anywhere else.

Every bottle becomes:

• A conversation piece

• A collector's item

• A memory from the event

And that's exactly what made the Johnnie-O Plaza Del Lago opening so special.

The store was filled with guests enjoying the grand opening while waiting for personalized bourbon bottles.

One of My Favorite Projects Yet

Projects like this remind me why I love what I do. From the first traced illustration to the last bottle delivered, every step challenged me to become a better artist.

I'm incredibly grateful to the Johnnie-O team for trusting me with such an important milestone for their company. It was an honor to help celebrate the opening of the Plaza Del Lago store, and I can't wait to see where the next bottle painting project takes me.

Every illustration was engraved by hand to reflect the Johnnie-O lifestyle—from polos and golf to cocktails and coastal living.

Looking for a Chicago Bottle Painter or Live Event Artist?

If you're planning a luxury retail event, brand activation, corporate gathering, or private celebration, custom bottle painting and hand engraving creates a one-of-a-kind experience your guests will never forget.

At Letters from Elliott, I specialize in:

• Hand-painted bottles

• Live bottle painting

• Hand engraving

• Hot foil personalization

• Leather debossing

• Wood burning

• Modern calligraphy

• Fashion illustration

  
  

Serving Chicago, the Midwest, and clients nationwide, I love helping brands transform everyday items into meaningful keepsakes through handcrafted artistry.

Interested in custom bottle painting or live event personalization?  Contact me, I'd love to help bring your next event to life.