By Photographer Chris Wooley
The pin-up genre is the glamorous grandmother of modern-day boudoir. It blends sophistication, history, and a bit of sass. And it makes a fantastic addition to any portrait studio’s lineup. Some clients love the retro throwback to simpler times and polished beauty standards. Others are drawn to the rebellious rockabilly look, while some lean into the more risqué “cheesecake” style made famous by icons like Bettie Page.
What makes pin-up so powerful is its flexibility: it works for every body type, every age, and every level of modesty. Over the last 15 years, I’ve photographed thousands of people in this style – ranging from high school seniors to senior citizens – each celebrating their unique personality and charm. At my studio, Heads & Tails Photography in Spokane, Washington, pin-up portraits have become a signature offering, providing clients with an empowering and joy-filled experience.
Planning the Session
Every pin-up session begins with a planning meeting, either in person or via Zoom. This is where we nail down logistics like scheduling, pricing, and process – as well as the fun details: wardrobe, props, and hair and makeup notes. The key to success in this genre is personalization. Whether it’s a 1940s-inspired Rosie the Riveter or a 1960s cocktail party vibe, tailoring the session to the client ensures the portraits feel authentic and celebratory.
Building Variety: Four Looks
Each of these looks falls into a category.
PERIOD: For me, this is the 1920s-1960s. Usually we pick a decade and then find a corresponding outfit. The photograph style is heavily influenced by the genre. (Tip: check out the links below to see an indepth history of each of these decades in my History of Pin-up Project (NSFW))
THEMED: This look plays on the classic themes of the 1930s – 1940s calendar girls. Popularized by the Brown and Bigelow calendars, these feature pin-ups focused around specific looks or themes. Classically, these themes were excuses to create artwork and ranged from promoting tools to voting in the upcoming elections. I put a more contemporary twist on these looks, allowing for anything my subject is passionate about. One of the more popular looks is a classic “shop girl” with tools. But it could just as easily be StarWars, Horror Movies, Fishing, Sewing, Military, or Baking. The point is to have a theme.
SEXY: Most of my clients want to have at least one look that has a bit of sex appeal to it. Most of the time, we channel the 1950s-1960s cheesecake look inspired by Marilyn Monroe and Bettie Page. Frequently we’ll use corsets, garters, stockings, and other accessories to complete the look. It’s more glamour than skin (usually) in these styles. The attitude and dramatic lighting make all the difference.
Once we pick our themes and genres then we start tracking down the clothing for it. I do not have a client closest for wardrobe (but I do have lots of fun props). For the period looks, Amazon or online retailers (like PinUpGirlClothing.com) have great variety at decent pricing. Themed looks can usually be done using items the subject already owns. For instance, they may use their husband’s workshirt, or a favorite t-shirt. They also usually have props that match their interests, too. The Sexier looks usually require purchasing a corset, garter, and stockings. Although these can be found on Amazon, I find the quality to be hit or miss (regardless of price). I highly recommend OrchardCorsets.com for quality corsets that photograph really well.
Session Flow and Experience
Sessions are designed to be fun and comfortable, starting with the least restrictive outfits and finishing with more dramatic looks like corsets or hats. Professional hair and makeup artists help complete the transformation, creating polished styles that complement each outfit.
Bringing It to Life: Artwork & Products A couple of weeks after the session, clients return for their ordering appointment. This is where the magic of print brings pin-up to life. Many choose a signature metal print for its sharpness and vivid color, while others select canvas or mounted prints. Albums are incredibly popular in this genre, especially ACI’s Riveli Album with its thick pages, leather cover, and custom
box—perfect for showcasing multiple looks in a luxurious, retro-inspired presentation. Calendars are another client favorite, adding a nostalgic nod to the Brown & Bigelow calendar-girl tradition.
Pin-up portraits are more than just photographs: they’re experiences of empowerment, playfulness, and confidence. They allow clients to step into a glamorous, stylish persona while celebrating who they are today. As both a photographer and an educator, I encourage fellow portrait artists to explore this rewarding genre. Not only does it open creative doors, but it also provides opportunities for unique products and premium artwork sales. At Heads & Tails Photography, pin-up has become a cornerstone offering, inspiring clients and enriching our studio’s brand. So give pin-up a test drive; you’ll walk away refreshed, inspired, and maybe with a little extra sass in your step.
About the Author:
Chris Wooley, M.Photog., Cr., CPP, is a professional photographer and educator based in Spokane, WA. He specializes in headshots, branding portraits, and retro-inspired pin-up sessions at his studio, Heads & Tails Photography. A frequent speaker at national and state photography conferences, Chris is passionate about teaching photographers how to elevate their craft and their business. You can learn more about upcoming workshops (including pin-ups workshops) on his photography education website.