PegCity Pinup Pageant

PegCity Pineup 2019 WinnerYou could be crowned the Winner of the 2020 PegCity Pinup Pageant! Grand prize includes a sash and crown, a beautiful bouquet, a prize pack, a professional photo shoot and the cover of the 2021 PegCity Pinup Calendar!

The PegCity Pinup Pageant is proud to be an all-inclusive pageant! We welcome applications from all persons age 18+ regardless of gender identity, disability, ethno-cultural identity, or any other basis. All that we ask is that you bring some fierce, retro pinup style!

Round 1 – Applicants

$30 Application fee.
All successful applicants will:

  • Have their submitted photo(s) posted on the PegCityPinups Instagram page along with a short bio and link/tag to their social media account
  • Receive a Day Pass to The Winnipeg Tattoo Show to come watch the PegCity Pinup be crowned on Sunday, Feb 23rd!

Public Voting Begins!

Applications are open from October 15, 2019 – January 15th, 2020. Applicants will be posted on the PegCity Pinup Instagram feed as they come in, entry fee is received and applications are approved. The Top 15 contestants with the most likes on their photo on the PegCity Pinup Instagram account move on to Round 2. So promote yourself! Like, Share and get the word out to move on to the next round!

We suggest submitting professional photographs with your application to boost your chances. Please see the pageant rules regarding photo submissions at the bottom of this page.

Votes (the number of likes) are tallied up on January 16, 2020 at 00:00 and the top 15 contestants moving on to Round 2 will be announced January 16, 2020 at 08:00.

Round 2 – Top 15 Contestants

The top 15 contestants will compete live onstage in the PegCity Pinup Pageant on Saturday February 22rd, 2020 at The Winnipeg Tattoo Show. Round 2 categories will be CASUAL STYLE, FORMAL WEAR and SWIMSUIT & RESORT WEAR.

In addition to competing at the pageant, each of the Top 15 will get to:

  • Be professionally photographed by Dano Tanaka, which will be published in the 2021 PegCity Pinup Calendar!
  • Attend a Meet & Greet with PegCity Pinup and Winnipeg Tattoo Show sponsors, hosts and organizers.
  • Have VIP access to all 2020 Winnipeg Tattoo Show events.

Round 3 – Top 6 Contestants

All contestants move on to compete in Round 3 on Sunday, February 23. Round 3 category is TALENT. Following Talent the judges will tally their votes to crown the 2020 winner of the PegCity Pinup Pageant!

Round 4 – The Crowning

On Sunday, February 23rd we announce the Runner Up and crown the 2020 winner of the PegCity Pinup Pageant! Runner Up will receive a sash, a beautiful bouquet and a small prize pack.

The crowned winner of the PegCity Pinup 2020 will receive a crown, sash, a beautiful bouquet, tattoo time, $1000 to spend at The Foxy Shoppe – our main sponsor, a professional photo shoot for the 2021 PegCity Pinup Pageant Poster, a large prize pack and the cover of the 2021 PegCity Pinups Calendar! They will also have a spot on the judging panel for the 2021 pageant and VIP weekend access to the 2021 Winnipeg Tattoo Show.

All Top 15 contestants will receive a consolation pack with goodies generously donated by Winnipeg Tattoo Show and PegCity Pinup sponsors.


  • All contestants must be 18+ to enter. Proof of age may be required during application process.
  • Contestants must be able to attend the PegCity Pinup Pageant at The Winnipeg Tattoo Show, February 22 and 23, 2020 as well as a mandatory Meet & Greet and Pageant Rehearsal. Dates and times to be sent to approved contestants.
  • The pageant application fee is non-refundable and does not guarantee entry to the second round of the pageant.
  • Photos and videos submitted must not contain any nudity.
  • Selfies, photos and videos with a Snapchat filter or photos and videos that are too revealing will not be approved – this is a family friendly pageant!
  • Applicants must have a public Instagram account during application process and online voting.
  • All contestants must follow the code of conduct (emailed to each contestant) at all times. Failure to do so will result in the contestant’s ejection from the pageant.
  • International applications are accepted. We are thrilled to accept applications from all adults, of all genders, shapes, sizes and ethnicities.
  • This is a classy, family friendly event.
  • All contestants should represent an era, ranging from 1920’s to 1970’s. We encourage vintage props and attire.
  • All outfits, including swimsuits, must be family friendly!
  • Past PegCity Pinup Pageant winners must wait a minimum of 3 years before applying to compete again!

Enter here

Pageant Sponsors Boutique Foxy Shoppe
Evie Assault Living Canvas Tattoo, Winnipeg Canada

Beyond Flowers
Website | Instagram | Facebook

Dano Tanaka Photography
Website | Instagram

Boutique Foxy Shoppe
Website | Instagram | Facebook


Winnipeg's biggest tattoo show wouldn't be possible without the generous support of our following sponsors. Visit their websites! They rule.

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