Windy City Pin Up & North Shore Boudoir are Vintage Inspired, Body Positive, Pin Up & Boudoir Photography

We welcome all humans and are inclusive of working with folx of all identities, sizes, and experiences.

We are available for portraits, parties and special events.

Whether you're looking for a special treat for yourself, a gift for a significant other, or the best vintage party experience ever, we are here for you.

We are dedicated to transforming everyday beauties into timeless bombshells.

We are inspired by YOU,

We strive to capture the beauty of your body as it actually is. 

You are beautiful. You are enough. You do not need to be altered.

We create a safe and supportive space where positive self talk and self love is encourage and valued. 

We are 100% queer woman owned and operated.

We are committed to create for you an experience and memories that will last a lifetime.

We are here to serve you in our home studio, in your home, or on location.

Meet our Staff

Ashlee Dean Luna - Owner | Photographer

Ashlee has dedicated their life to supporting and celebrating humans through photo documentary and pin up. Am acclaimed and internationally published photographer, she has owned and operated Windy City Pin Up since it's start in 2010. You can view Ashlee’s full portfolio here.



Laura Wilson - Partner | Hair & Make Up

Laura is fully trained in theatrical hair and makeup and has dedicated her life to the art of pin up. Her vast knowledge of historical periods and vintage collectibles helped get Windy City Pin Up off the ground and she's been an integral partner in operations since it's start in 2010. You can view Laura’s full portfolio here.



Pin Up Party Staff {if you book a party with us larger than three guests, you'll likely get to meet these lovely ladies as well!}

Alla Yanovsky - Make Up

Rachael Aprill - Make Up

Ren Picco-Freeman - Hair