PegCity Pinup Pageant

You could be crowned the Winner of the 2026 PegCity Pinup Pageant!

Grand prize includes a $500 cash prize, sash and crown, a beautiful bouquet, a prize pack, and a professional photo shoot! The PegCity Pinup Pageant is proud to be an all-inclusive pageant! We welcome applications from all person’s 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

$35 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 Sunday Pass to The Winnipeg Tattoo Show to use Sunday May 3 (valued at $20).

Applications are open from Monday, February 23rd to Thursday, April 9th. Applicants will be posted on the  PegCity Pinup Instagram feed feed as they come in, entry fee is received and applications are approved. Promote yourself! Like, Share and get the word out. We want to see your favourite people cheering you on in the crowd!

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

Round 2 – Stage Presentation and Pageant

All contestants will compete in the stage portion Round 2 on Sunday, May 3, 2026. The categories will go as follow; Beach wear/Intro question, Talent, and Formal Wear. Following Formal Wear while the Future Tattoo Artist= awards presented by The Winnipeg Tattoo Show are taking place the judges will tally their votes to crown the 2026 winner of the PegCity Pinup Pageant!

Round 3 – The Crowning

At 4:30pm following the Future Tattoo Artist awards we announce the Runner Up and crown the 2026 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 2026 will receive a crown, sash, a beautiful bouquet, a cash prize of $500, a professional photo shoot for the 2027 PegCity Pinup Pageant Poster and calendar, and a prize pack. They will also have a spot on the judging panel for the 2027 pageant and VIP weekend access to the 2027 Winnipeg Tattoo Show.

All contestants will receive a consolation pack with goodies as well as a 2027 pinup pageant calendar (available for pickup at a future date) generously donated by Winnipeg Tattoo Show and PegCity Pinup sponsors.

Rules

• 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, May 3, 2026 as well as well as the Pageant Rehearsal. (Dates and times to be sent to contestants.)
• The pageant application fee is non-refundable.
• 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.
• 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 so please ensure all outfits, including swimsuits, be family friendly!
• All contestants should represent an era, ranging from 1920’s to 1970’s. We encourage vintage props and attire.
• Past PegCity Pinup Pageant winners must wait a minimum of 3 years before applying to compete again!

Enter here