Three Decades Of Chicago Institutions Trusting Us With Their Name
Trusted By
Certified MBE, DBE, ACDBE And Veteran Owned
From humble beginnings as a retail store at one of Chicago's most iconic attractions, D.C. Mad Hatter has grown into a trusted name in custom embroidery and screen printing.
Our BEP certification is issued by the State of Illinois Commission on Equity & Inclusion, and it is accepted by the City of Chicago, CTA, Cook County, Illinois DOT, Metra and Pace. Spend with us counts toward the participation number you have to hit. We are also a graduate of the SBA 8(a) program.
Ensuring That Diversity and Excellence
Remain At The Heart Of Everything We Do.
Derryl Caldwell is more than just an entrepreneur, he is a leader, a visionary, and a community advocate. With a strong foundation in Aviation Flight Management, a distinguished service record in the United States Navy, and a deep understanding of business operations, Derryl built D.C. Mad Hatter on the principles of resilience, innovation, and strategic growth.
United States Navy
His journey began in the U.S. Navy’s Officer Program from 1990 to 1993, where he honed his leadership and operational skills
Southern IL University
After earning his degree from Southern Illinois University, he served as Director of Operations at Green Brothers Construction before forging his own path in business.
Mad Hatter - Navy Pier
Established in 1996 by visionary entrepreneur Derryl Caldwell, our company has been a staple of Chicago’s Navy Pier, welcoming visitors with apparel that speak to individuality and excellence.
University of Illinois
His pursuit of excellence led him to UIC’s Executive MBA program, where he sharpened the skills that have guided him through nearly three decades in business.
We Are More Than A Business
We Are A Movement
A true craftsman and recognized leader in custom branding and promotional apparel, Derryl is a proud member of the National Network of Embroidery Professionals (NNEP). His commitment extends beyond business: through strategic partnerships and volunteer initiatives, he works to uplift his community and has built lasting relationships with organizations including
National Network of Embroidery Professionals
Black Contractors Owners & Executives
Chicago Urban League Retail Next Program
Hispanic American Construction Industry Association
100 Black Men of Chicago
Project H.O.O.D.
Kappa Alpha Psi Fraternity
Chicago Football Classic Committee
We believe in the power of community, the strength of collaboration, and the lasting impact of quality craftsmanship. Whether you need custom embroidery, screen printing, branded apparel, or a partner who understands your vision, we’re here to bring it to life.
Support A Cause You Care About
Water
Clean Water For Rural Villages
Education
Education For Every Child
Food
Emergency Food Relief Program
Pure Water
Provide Safe Drinking Water.
Literacy
Empower Underprivileged Children
Food Security
Critical Nutrition and Food Crisis
Join Our Team & Help Us Change More Lives Together
Give your time and skills to a worthy cause. Every hour you volunteer creates ripples of hope.
Become A Volunteer
What Our Donors Are Saying
"Hopeful made it incredibly easy to see exactly where my donations go. I've never felt more connected to a cause."
"Volunteering with this team changed my perspective on giving back. Truly a life changing experience for me."
"Our partnership with Hopeful has allowed our company to make measurable, transparent impact."
Meet Some Of Our Amazing
Volunteers
Find Answers To Common Questions
Most of what people ask comes down to art files, timing, and what a finished piece will actually look like. Here are the straight answers. If yours is not here, call and ask.
