Windy City Pin Up is Vintage Inspired, Body Positive, Pin Up & Boudoir Photography

We welcome all humans and are inclusive of working with folks 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% 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 Chicago studio, located just north of Ashland and Irving Park, in the Lakeview Neighborhood.

Meet our Staff

Ashlee Wells - Owner | Photographer

Ashlee has dedicated her life to supporting women through photo documentary and pin up. A noted and published photographer, she has owned and operated Windy City Pin Up since it's start in 2010. Part ninja, part geek, part girly girl enthralled with  all that encompassed life in the 40's and 50's



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. Your transformation begins in her chair - brushes, colors, curlers & combs, she moves mountains to create our polished looks. 



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