Completed contest

Awesome, creative T-shirt needed to make our business more fun!

Jessica4 needed a new t-shirt design and created a contest on 99designs.

2 winners were selected from 38 designs submitted by 14 freelance designers.


One of the designers who made it happen

Winner - pmo
PMO actually understood what I wanted before I knew what I wanted. Superb work again. He just gets it right first time.
- jodeverill

How Jessica4 started their t-shirt journey

Brand name

Cities Digital


We are an energetic, creative small business doing software consulting in the electronic content management field. Our team works hard to design, implement and support out of the box and custom software solutions for our clients. Mainly, we help them get their paper records scanned in and stored on the computer to improve security, efficiency and access issues. Our business values thinking outside the box, finding solutions and answers, building strong client relationships, and making software approachable and usable. We are involved in helping clients go paperless.

We're coming up on our 10 year anniversary (Yeah! Made it through the recession!) and now that we've been around awhile, we are investing more into our marketing and image. We got a shiny new logo and color palette to celebrate the occasion and now we'd like to give people the opportunity to traipse around town proudly displaying it.

Our solutions make our clients sigh with relief, but our t-shirts make them fall asleep. We could really use some help bringing our company's creative spirit into a t-shirt design.

Tell us a bit about who you are and the people you reach

We'd like our t-shirts to appeal to our employees, clients and other general fans. This means, adult men and women, who can be anything from a government employee to a financial planner. They could range in age from early 20's and up.

We'd like them to be able to wear it to work, so nothing crude or offensive.


We're looking for a cool graphic and/or witty illustration. It could be a design based around a funny saying or mostly an abstract design. We really want it to have strong design, not just be funny/interesting text on a shirt.

We'd like our logo to be incorporated somehow into the design, but not be super prominent.

We want it to be a shirt that people will wear because it's cool or the design is a conversation-starter, not because they need another boring free t-shirt to throw on to mow the lawn.

Check out our website for information on what we do:

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