Derby Contest Preview #786: Awkward


That’s it, your only prompt.

Just remember, people will have to WANT to wear your designs in public. On a t-shirt.

We won’t print anything sexually explicit. Or poopy. Or offensive. Or political. Or on cream.

*This Derby begins MONDAY November 2nd at 8pm, CST. & ends MONDAY November 9th at 8pm, CST. The three winning designs will be featured as the Daily offers Tuesday-Thursday. Great designs that don’t win may be included in an Editor’s Choice sale on Friday, so be sure to check back and see who makes the cut!

Please be sure to have your artwork ready to submit with your entry as part of the new submission process!

If you want to submit any off-topic designs, submit here!

If you are new to the derby and want to participate, WELCOME! Also, in addition to the rules above please check out our content guidelines here so you know what works and what doesn’t over here at Woot!

You can also download updated templates for your artwork over here . Happy designing


Awkward is my wheelhouse. And I’m riding a unicycle with a flat.

1 Like

Where is the line between Awkward and Tacky? Asking for a friend.

Awkward is so hard to illustrate, but always up for a challenge!

This is perfect. I always say I am going through my awkward stage!

My rule of thumb in life is that if I cannot see the line in between two things it’s because I’ve already crossed it :slight_smile:

Art is never finished, it is abandoned… You know you are finished when one more element, line, dot, etc. will ruin the work. In order to learn when to stop one must repeatedly ruin their own work. The same is true for tacky vs awkward.


This is the Thursday motivation I needed. GONNA RUIN SOME WORKS NOW!!! :smiley:


This makes me appreciate the talented writers, actors, producers, and staff on shows like The Office. They make it appear seemless.