The Awkward challenge winner is here!

69 designs /
printed design / 32,687 votes placed

The Awkward Years

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The challenge was

Create an awkward t-shirt design.

Many of us were our most awkward selves in high school. Social misfit Jenna, the main character of MTV’s Awkward., is no exception. Even if you haven’t followed Jenna’s saga*, chances are you can relate to the drama, confusion, and downright awkwardness that comes with being a teenager and human being in this world.

So conjure up all the social grace and assurance you (think you) lack, and channel it into an awesome and awkward t-shirt design! Pull out your most awkward family photo for inspiration. Reminisce about the good ol’ days of braces and the horrible haircut you gave yourself once. Think very hard about an embarrassing experience you tried to forget. And get to work creating your most awkward design yet!

*Jenna meets Matty, then meets Jake, then cheats on Jake with Matty, then her best friend starts dating Jake, and now Jenna’s with Matty.

Sorry, only residents of the contiguous United States and the District of Columbia are eligible to win this competition and be awarded the grand prize. However, designs submitted by members of the Threadless community residing outside of those areas may be considered for printing as part of the ongoing Threadless challenge. The official rules governing the contest are set forth under the “Legal stuff” link.

The winner received

  • $2,000 cash

  • $250 gift code

  • Trip for 2 to visit the set of MTV's Awkward. in Los Angeles, California. Includes round-trip flights from a major U.S. airport, one night hotel stay, personal tour of the set, and transportation in LA (if winner lives within 150 miles, MTV reserves the right to substitute ground transportation for the flight)

  • Your design featured in Jenna's room on Awkward.

  • Your design printed on t-shirts and wall art

  • Other designs chosen for print from this challenge will receive compensation based on the product printed on and the quantity printed. This applies for submissions received from outside of the contiguous United States and the District of Columbia

Designs from this challenge



This MTV series takes an irreverent look at the conflict, chaos and humor that defines teenage life through the eyes of 15-year-old Jenna Hamilton, whose life begins to change when a simple accident becomes an epic misunderstanding and is blown way out of proportion.

Narrated in the first-person voice of Jenna's blog posts, Awkward. captures the humor within the struggles and experiences everyone can relate to from their formative years. The series picks up in the aftermath of the accident, as she must deal with a new not-so-fun stigma, while at the same time managing the other daily drama that comes with being a teenager. From a secret relationship with a popular guy, to being undermined by a mean girl, and parents who just don't get it - Jenna's misfortune will eventually serve as the catalyst for amazing change, but it's not without some missteps and mishaps along the way.