2020 Miss Iola Pinup Contest is Canceled.
See you in 2021!

The Perfect Event for Vintage Lovers
With over 300 acres that showcase more than 2,200 show cars, 4,200 swap spaces, 1,000 car corral spaces and 1,600 camping spaces, the Iola Car Show transforms a little town with a population of 1,301 into a massive event with roughly 100 times that number in attendance.
The Miss Iola Pinup Contest brings vintage lovers and pinup gals from all over the Midwest to one of the largest and longest running car shows in America.
Join us in crowning the 4th Annual Miss Iola
Brought to you by Ginny Rosewater and pinup group The Midwest Rockabeauties, the Miss Iola Pinup Contest will be back for a fourth year - with even bigger prizes, bigger fanfare, and bigger personalities!
Location
Iola Car Show 
Winner's Square Stage
Iola, WI Car Show Grounds
Date/ Time
The contest will start:
TBA
Contest Format/ Rules
ROUND 1
Posing and Bios.
Each contestant will come on stage and do three poses while the MC reads your bio (put together from the registration questions – it gives the audience and judges a little feel for your personality).
ROUND 2
Question and Answer.
The top 13 contestants from Round 1 will go into Round 2 where they will be asked a question related to pinup/40s-60s (the list of possible questions will be given to you a month in advance).
ROUND 3
The Final Round.
Round 3 will consist of the top 5 contestants. All will be asked the same question. The top 3 will then be crowned and have their photo taken.
Contestants who make it to the 3rd round are welcome to change their outfit but it's not mandatory.
2019 Prizes
1st Place - Miss Iola Blue Ribbon
• Shannon Brooke Photoshoot Aug. 6th
• Feature in Pinup Kulture Magazine
• Custom Painting by D.H. Rodriguez
• Vroom! by Shannon Brooke (courtesy of Working Class Publishing)
• Pinup Cutie T-shirt
• Mollywear Custom hairflower

2nd Place - Miss Classic Cutie
• Buxom Boudoir Photoshoot
• Stocking Seams & Lipstick Queens 
by Claire Seville (courtesy of Working Class Publishing)
• Pinup Cutie T-shirt
• Mollywear Custom hair flower

3rd Place - Miss Hotrod Honey
• Cardinal White Photoshoot
• Dollface Vintage by Cherry Dollface (courtesy of Working Class Publishing)
• Pinup Cutie T-shirt
• Mollywear custom hair flower

Contestant Prizes
Every entrant received an amazing gift bag with world-class prizes from our sponsors, including:
Hollyville discount code
The Revival hair accessory & discount code
Greg’s Speed Shop discount code
Working Class Publishing t-shirt
Flairware Boutique hair bows
Menace Monster Art stickers
2019 Judges
Carmen Lee - Frontwoman of 'Carmen Lee & The Tomorrow River Two', Pinup Model, Photographer at Lucky Penny, and Retro Clothing Vendor at Big Star Vintage.
Carmen Lee - Frontwoman of 'Carmen Lee & The Tomorrow River Two', Pinup Model, Photographer at Lucky Penny, and Retro Clothing Vendor at Big Star Vintage.
Kelly Ballard - Founder of Working Class Publishing - International Publisher of Pinup, Art, and Vintage Lifestyle books.
Kelly Ballard - Founder of Working Class Publishing - International Publisher of Pinup, Art, and Vintage Lifestyle books.
Ruby Roundbottom - Mother of two and winner of the 2018 Miss Iola Pinup Contest, runway model in the 2018 “A Retro Affair” fashion show and owner of Pinup Cutie Etsy store.
Ruby Roundbottom - Mother of two and winner of the 2018 Miss Iola Pinup Contest, runway model in the 2018 “A Retro Affair” fashion show and owner of Pinup Cutie Etsy store.
Your Host 
Ginny Rosewater
Ginny Rosewater - Local Pinup icon and hardworking Midwestern gal Ginny brings you the 3rd Annual Miss Iola Pinup Contest!
Ginny Rosewater - Local Pinup icon and hardworking Midwestern gal Ginny brings you the 3rd Annual Miss Iola Pinup Contest!
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