Celebrating 20 Years of Crooked Monkey: From Cool Tees to Transforming Brands

As we celebrate 20 Years of Crooked Monkey, we look back on how far we’ve come. Twenty years ago, Crooked Monkey started as a scrappy t-shirt company with big dreams and a small budget. Fast forward to 2025, and we’re a full-blown merch agency, transforming companies into brands with premium swag that people actually want to wear and use. How did we get here? A lot of grit, creativity, and a firm belief in saying “yes.”

The Beginnings

Crooked Monkey’s journey started with a bold T-shirt idea at the University of Maryland. Micha Weinblatt and his crew printed “F*ck Duke” shirts, a risky but successful move that had them dodging dorm security and police. The success of these shirts helped them launch a brand that has now evolved into one of the largest custom merchandise agencies in the U.S. Micha didn’t just ride on luck—he hustled through challenges, from navigating the retail world to surviving a major business setback, ultimately landing major clients like Lord & Taylor.

Growing Up Without Growing Old

In the early years, Crooked Monkey’s growth was a grind, but Micha’s dedication paid off. After a major setback left him as the sole employee, his resilience and passion led him to secure a major deal with Lord & Taylor. From there, the company’s reputation grew, leading to partnerships with major retailers like Bloomingdales and Saks. Even through the 2008 market crash, Crooked Monkey adapted, shifting from humorous tees to upscale designs and expanding into local businesses.

Crooked Monkey’s success didn’t come from following the rulebook. It came from tossing it out the window. As our values say, “we take our work, not ourselves, seriously.” We’ve stayed team-first, built trust through relationships, and said “yes” even when it scared us. (Spoiler: those are the best opportunities.)

Here’s the truth: we’re obsessed with swag. But we’re even more obsessed with solving problems creatively. Over the years, our collective personalities and the “figuring it out” mindset have shaped who we are. It’s not about fancy presentations or corporate jargon. It’s about understanding the why behind every project and creating swag that speaks for itself.

Values That Drive Us Forward

At Crooked Monkey, our values aren’t just words on a wall – they’re the playbook for everything we do. We’re Team First means we win and lose together, always putting collaboration at the forefront. We Care because getting the details right and building genuine relationships is what sets us apart. We Say Yes because growth lives outside the comfort zone, and figuring things out has always paved the way for our success. We Dig Deeper to uncover the why, solving problems with thoughtfulness and intent. We Value Time because efficiency is key – we respect our clients’ time as much as we do our own. And Creativity Runs Through Our DNA – from designing merch people love to sourcing products that stand out, we never settle for boring. These values aren’t just how we operate – they’re how we’ve built lasting partnerships and a culture we’re proud of.

• We’re Team First: From account managers to designers, we’re in this together.
• We Care: Details matter. Relationships matter. Sometimes, going above and beyond means hand-delivering that package.
• We Say Yes: Growth comes from pushing boundaries. We started small, but saying “yes” led us to where we are today.
• We Dig Deeper: Understanding the why makes us better partners.
• We Value Time: Efficiency matters. We don’t waste yours or ours.
• Creativity Runs Through Our DNA: Beautiful designs. Interesting products. Merch people actually love.

These values are the reason our clients trust us. We don’t just deliver products – we deliver experiences.

Big Ideas, Bigger Reach

Crooked Monkey runs on big ideas and a bigger footprint. We’ve got boots on the ground in D.C., Louisville, Nashville, Philly, Denver, Vegas, NYC, and Miami, plus production running both locally and overseas. We craft high-quality merch wherever it makes the most sense for each project. Our global crew works across time zones to bring ideas to life—fast, smart, and always on point.

Looking Ahead to 20 More Years

As we celebrate 20 years of Crooked Monkey in 2025, we’re just getting started. The world of branded merchandise keeps evolving, and we’re here for it. From custom backpacks to beautifully designed apparel, we’ll keep transforming companies into brands and making swag that stands out.

Here’s to 20 years of figuring it out, saying yes, and building something we’re proud of. And here’s to 20 more.