True North Pin Up

Contest Prep Hub

Everything You Need to Know Before You Apply, Step on Stage, or Slip on Your Heels

Pin up contests are about confidence, creativity, and community—but they’re also real events with real logistics, expectations, and care behind the scenes.

This page exists so you can decide, prepare, and participate with clarity—not confusion.

Whether you’re a first-time applicant or a seasoned stage siren, welcome. 💋

Before You Apply:

Is This Contest Right for You?

Budget Checklist for Contestants

Application & Admin

  • Application fee

Travel & Accommodations

  • Transportation

  • Parking

  • Hotel

  • Meals

  • Time off work

Wardrobe & Styling

  • Outfits

  • Shoes + backups

  • Hosiery (extras!)

  • Accessories

  • Undergarments / shapewear

Hair & Makeup

  • Products and tools

  • Touch-up items

  • Optional professional services

Event Essentials

  • Emergency kit

  • Comfortable off-stage shoes

  • Water, snacks, charger

Optional Extras

  • Professional photos

  • Prints or promo materials

If this feels exciting—not overwhelming—you’re probably ready.

Not every contest fits every season of life—and that’s okay.

Before applying, ask yourself:

  • Do I have the time and energy for a multi-day, public event?

  • Can I budget for travel, wardrobe, and time off without stress?

  • Does this contest align with my values, vibe, and goals?

  • Am I excited by the experience—not pressured into it?

Choosing your stage wisely is part of the glow-up.

So You’re Signing Up…

First of all—hell yes.

Whether this is your very first pin-up contest or you’ve danced across more stages than you can count, signing up is a bold, exciting choice. This page exists so you know exactly what you’re stepping into, how to prepare, and what to expect—every step of the way.

No guessing. No gatekeeping. No drama.

Just clarity, confidence, and community.

The Contestant Journey: Apply, Selected, Prep, Event Weekend, Aftercare — showing the full lifecycle of a True North Pin Up contest experience.

Your Questions, Answered

  • Before you hit “submit,” pause for a moment and check in with yourself.

    Ask:

    • Am I excited about a multi-day, public, professional event?

    • Do the values of this contest align with mine?

    • Am I choosing this because I want to—not because I feel pressured?

    • Does this feel like a stretch in a good way, not stress in a bad one?

    Pin-up is not a race. Choosing the right stage for this season of your life is part of the magic.

  • Application fees are not “pay-to-win.” They exist to support the real infrastructure behind a professionally run, community-led contest.

    Your fee helps cover:

    • Booth and show fees

    • Insurance and event requirements

    • Application platforms and admin systems

    • Contest planning, coordination, and communication

    • Prizing, presentation, and show logistics

    • Clear standards that protect the community

    All of this work happens before anyone ever steps on stage.

    If the fee isn’t the right fit, that’s okay. This contest may simply not be the right one right now.

    Want to know more? Read our blog post about this here.

  • This is a World of Wheels Exclusive: To create the best possible experience, the World of Wheels contest is limited to 15 contestants.

    Step 1: Eligibility Screening

    All applications are reviewed to ensure they meet minimum requirements:

    • Full availability for all event days

    • A complete application

    • Agreement to the Code of Conduct

    • Understanding of the professional, public nature of the event

    Only eligible applications move forward.

    Step 2: Judges’ Choice Selections

    A small number of contestants (3–5 spots) are selected by the judging panel based on:

    • Stage presence potential

    • Professionalism and attitude

    • Alignment with the World of Wheels brand

    • Balance and variety in the overall show

    Step 3: Curated Lottery Draw

    The remaining spots are filled through a randomized draw from the pool of qualified applicants.

    This approach:

    • Maintains fairness and transparency

    • Eliminates favoritism

    • Gives new and returning contestants equal opportunity

    All applicants are notified by a certain date.

  • Once you’re in, you’re supported—clearly and consistently.

    Our 5-Step Communication Plan

    1️⃣ Confirmation & Welcome
    You’ll receive a welcome email confirming your spot, next steps, and our Anti-Bullying & Inclusion Policy. Culture matters here.

    2️⃣ The Contestant Guide (2–3 weeks out)
    Includes:

    • Event schedule and call times

    • Stage flow and expectations

    • Appearance and participation details

    • Judging categories and rubric

    • Code of conduct reminders

    • Optional social media graphics

    3️⃣ Photographer Access (10–14 days out)
    You’ll receive access to a booking calendar with Janelle of Miss Friend Photography, in collaboration with Rose Chantel of AB Charity Collaborations, ensuring equal, respectful access for all contestants.

    4️⃣ Event Timeline + After-Party Details (5–7 days out)
    Your full schedule so you can plan your days confidently and calmly.

    5️⃣ Final Check-In (2–3 days out)
    Reminders, contacts, your rubric (again), and a whole lot of hype 💖.

  • Here’s how a typical contest unfolds:

    • Introduction: You’re called on stage while your bio is read

    • Interview: A question designed to showcase your personality and passion

    • Posing: Three signature pin-up poses

    • Exit: Confident walk-off

    • Finale: All contestants return to the stage one by one

    Knowing the flow ahead of time helps nerves stay calm and confidence stay high.

    Keep in mind, each event is different and for multi day events you may be running through different parts of the event each day.

  • We expect:

    • Professionalism

    • Kindness and respect

    • Supportive backstage energy

    • Grace in wins and losses

    • Responsible social media conduct

    No gossip. No bullying. No tearing others down.

    Pin-up is community before competition.

  • Judging is structured and blind.

    Judges see stage names only—nothing else.

    Our panels include:

    • Women active in the pin-up scene

    • Past winners

    • Veteran pin-ups

    • Empowering women who understand performance and presence

    Judges score what they see on stage, using a clear rubric—just like teachers grading an assignment.

    Scoring is submitted via Google Forms that:

    • Automatically calculate totals

    • Feed into a spreadsheet

    • Eliminate discussion, influence, or bias

    No conversations.
    No favouritism.
    No greasy nonsense.

  • At True North Pin Up, we don’t just crown winners—we celebrate icons.

    👑 Queen of the Show (1st Place)
    Vintage authenticity, radiant confidence, unforgettable presence.

    👒 Dame of the Day (2nd Place)
    Grace, grit, and undeniable charm.

    💋 Doll of the Day (3rd Place)
    Sweet, stylish, bold, and full of heart.

    🌹 Miss Gracious (Fundraising Award – Drumheller Exclusive)
    Honouring generosity, community leadership, and fundraising impact.

    Vintage values. Modern impact.

  • Winning is a moment.
    Participating is an experience.

    Winners receive:

    • Clear next steps

    • Support in sharing their win

    • Respect for boundaries and availability

    If you don’t win:

    • You are still valued

    • You may request scores or feedback

    • Your presence mattered

    Grace matters—on every side of the results.

How to Prepare for the Stage

  • Rooted in the glamour of the 1940s–50s, pin-up celebrates confidence, curves, and character. Icons like Bettie Page and Marilyn Monroe offer inspiration—not comparison.

    Key elements:

    • High-waisted silhouettes, fitted dresses, swing skirts

    • Victory rolls, pin curls, Bettie bangs

    • Winged liner, bold lips, defined brows

  • Your outfits should honour the aesthetic and make you feel unstoppable.

    • Practice moving and posing in them

    • Plan accessories thoughtfully

    • Comfort and confidence always win

    • Practice styles you can reliably recreate

    • Use strong-hold products

    • Bring touch-up supplies

    • Drama is encouraged—meltdowns are not

  • Pin-up is a performance.

    • Practice classic poses

    • Make eye contact

    • Let your personality lead

    • Confidence reads louder than perfection

  • Your theme should feel like you, through a pin-up lens.

    Consistency matters:

    • Outfits

    • Hair & makeup

    • Props and accessories

    • Poses and movement

    Think of your stage time as a short story—with a beginning, middle, and end. Judges love clarity, commitment, and intention.

  • Interview questions are meant to highlight you, not trip you up.

    Be ready to speak about:

    • Why pin-up matters to you

    • Your style and inspiration

    • Empowerment, confidence, and self-expression

    Practice speaking clearly and honestly. Heart > scripts.


The Bottom Line

Our contests are built with intention, structure, and heart.

You are never left guessing.
You are never just a number.
You are always respected.

If this feels aligned—welcome.
If not, that’s okay too.

Choose the stages that honour who you are right now.

Some inspiration from previous events

Potential Questions for a Pin-Up Contest Interview

The most daunting part of the pin up show, is always the on-stage questions. Have no fear dolls, we have you covered with some great ideas for questions.

Personal and Style Questions:

  1. What inspired you to enter this pin-up contest?

  2. Who is your favorite pin-up icon and why?

  3. How do you define your personal pin-up style?

  4. What does being a pin-up mean to you?

  5. How do you incorporate vintage fashion into your everyday life?

  6. Can you describe your favorite pin-up look/outfit?

  7. What do you love most about the pin-up community?

  8. How do you prepare for a pin-up photo shoot or contest?

  9. What is your favorite era of fashion, and why?

  10. Who are your style influences outside of the pin-up world?

  11. How do you feel when you dress in pin-up style?

  12. What are your go-to accessories for completing a pin-up look?

  13. How do you stay true to your personal style while embracing the pin-up aesthetic?

Historical and Cultural Questions:

  1. Can you tell us a bit about the history of pin-up culture?

  2. How do you think pin-up culture has evolved over the years?

  3. What role did pin-up art play during World War II?

  4. How do you think modern pin-up differs from vintage pin-up?

  5. Why do you think pin-up culture remains popular today?

  6. Who are some lesser-known pin-up artists or icons you admire?

  7. What historical events or movements have influenced pin-up fashion the most?

  8. How do you think pin-up culture intersects with other vintage subcultures?

Thematic and Creative Questions:

  1. What theme did you choose for this contest, and why?

  2. How did you develop your theme through your outfits and performance?

  3. Can you walk us through the inspiration behind your contest look today?

  4. How do you come up with new and creative pin-up ideas?

  5. What’s your favorite prop to use in a pin-up shoot or performance?

  6. How do you select your wardrobe for themed pin-up events?

  7. What challenges do you face when creating a cohesive theme?

  8. How do you incorporate your theme into your stage presence and poses?

  9. Can you share a memorable experience where your theme made a big impact?

Personal Impact and Philosophy Questions:

  1. How has participating in pin-up contests impacted your life?

  2. What message do you hope to convey through your pin-up persona?

  3. How do you think pin-up culture can empower individuals today?

  4. What advice would you give to someone new to the pin-up scene?

  5. How do you balance modern life with your love for vintage style?

  6. What personal growth have you experienced through pin-up modeling?

  7. How do you handle criticism or negative feedback about your style?

  8. What role does body positivity play in the pin-up community for you?

  9. How do you use pin-up modeling to express your individuality?

  10. In what ways has pin-up culture helped you build confidence?

Empowerment and Inspirational Questions:

  1. How does pin-up culture promote body positivity and self-acceptance?

  2. Can you share a story about a time when pin-up modeling empowered you?

  3. What do you think is the most empowering aspect of the pin-up lifestyle?

  4. How do you encourage others to embrace their unique beauty through pin-up?

  5. What impact do you hope to have on the pin-up community?

  6. How does pin-up fashion allow you to challenge societal norms?

  7. What does female empowerment mean to you in the context of pin-up culture?

  8. How do you support and uplift fellow pin-up enthusiasts?

  9. What initiatives or causes are you passionate about within the pin-up community?

  10. How do you use your platform as a pin-up model to inspire others?

  11. What role does diversity play in the empowerment message of pin-up culture?

  12. How can pin-up culture be more inclusive and supportive of different body types and backgrounds?

Fun and Lighthearted Questions:

  1. If you could have dinner with any pin-up icon, who would it be and why?

  2. What’s your go-to song to get into the pin-up spirit?

  3. If you could live in any decade, which would it be and why?

  4. What’s the most fun you’ve ever had at a pin-up event?

  5. How do you relax and unwind after a contest or photo shoot?

  6. What’s your favorite vintage-inspired activity?

  7. If you could only wear one pin-up outfit for the rest of your life, what would it be?

  8. What’s your favorite pin-up-themed movie or TV show?

  9. Do you have any funny or memorable mishaps from past contests or shoots?

  10. What’s your favorite treat to indulge in after a successful performance?