Drop the Obsession with “Pretty” Portrait Photography

Evolve your portrait photography from pretty to powerful with these tools for meaningful connection. (Featuring: MAE B. PHOTO, TY PENTECOST PHOTOGRAPHY, and CRYSTAL ANNE PHOTOGRAPHY)


You can’t go wrong with a pretty portrait. But what if you’re ready to evolve your work from pretty to meaningful? What steps do you take to infuse genuine emotion and story into your portrait photography?

These three photographers agree: it’s all in the client interaction. While conventional wisdom says people are either photogenic or, well… not, the truth is this: there’s a captivating photograph inside everyone. It’s up to you to lure it to the surface.


Drop the Obsession with "Pretty" Portrait Photography
Portrait of Mae B.

Peel Back the Layers

Mae B. is a Youngstown, Ohio, photographer who prefers to focus on conversation, allowing “poses” to occur organically. Subtle expressions and light shifts in movement can speak more loudly than any hip-pop or “show-me-your-pearly-whites” smile.

“It’s about peeling back the layers to get that true authenticity. Then I know people won’t just see the photo; they’ll feel it.” – MAE B.

But how do you create a quick connection with a client you don’t meet until shoot day? How do you strike up authentic conversation with someone who may be shy or awkward? Or what if you’re shy or awkward?

Drop the Obsession with "Pretty" Portrait Photography: Monochrome portrait of elegant Black woman photographed close-up with her eyes gently closed and a smile on her face. She wears a beaded headpiece and stands before a quiet pond. Photographed by Mae B.
Photo by Mae B. Photo

Learn Your Client’s Story

Great conversation requires two elements: speaking and listening. If you’re a natural talker, slow yourself down and actively listen. If you’re a natural listener, engage thoughtfully with what your client shares.

Mae photographed Janel, a woman working through a time of extreme challenge and personal growth. For strength and comfort, she was digging deep to discover her best, truest self – and Mae was determined to photograph that inner light and power.

Drop the Obsession with "Pretty" Portrait Photography: A woman stands in a wooded pathway wearing a maroon linen blouse and a gold beaded headpiece. Photographed by Mae B.
Photo by Mae B. Photo

“Janel loved short hair, so she shaved her head. She’s always been crafty, so she carved out time for making. She loves writing, so she started a blog. Janel cast her fear aside and started DOING. And more than anything, I wanted to showcase all of who Janel IS. This meant the struggles along with the happiness; the joy in her smile and the pain in her eyes.” – MAE B.

According to psychologist Dr. Leon F. Seltzer, our desire to feel understood is even greater than our desire to feel loved. When we take the time to learn our clients’ stories, we allow them to feel seen and heard. Then – and only then – can we expect them to reveal their deeper selves to our cameras.

Everyone has a story. Are you listening?

Drop the Obsession with "Pretty" Portrait Photography
Photo by Mae B. Photo

Photograph People Who Motivate You

Think about your most awkward dates… The office parties you couldn’t wait to escape… The obligatory kid birthday parties you’d always hoped to avoid…

Why were those experiences so unpleasant? Because those people weren’t your people.

When you photograph the right clients, the connections will come more naturally, and the conversation will flow more easily. Let your natural attractions guide you to your ideal clientele.

“The thing I love about photographing women is showing them how other people perceive them, and how their inner beauty shines through to their exterior.” – MAE B.

Drop the Obsession with "Pretty" Portrait Photography: Color diptych of elegant Black woman wearing red linen garments and gold beaded headpiece. She's standing beside a quiet ponnd at dusk. Photographed by Mae B.
Photos by Mae B. Photo


Enable A Transformation

Ty Pentecost is a Greater East Bay, California, photographer who shoots primarily weddings; but she leaves room in her busy schedule for portrait photography, too. She photographed Mary, an aspiring young model who was over-the-moon to be photographed professionally.

Even eager clients, however, have insecurities. Ty encourages an environment of confidence by enlisting hair and makeup artists to help her clients feel their most beautiful.

Drop the Obsession with "Pretty" Portrait Photography
Portrait of Ty Pentecost

Set the Tone

“The most rewarding thing about photographing women is the transformation I see throughout their photo experience. It starts in hair and makeup: their confidence begins to shine through, and I see a renewed sense of power that is absolutely beautiful.” – TY PENTECOST 

If full hair and makeup provision aren’t your style (or in your client’s budget), find other ways to support their readiness.

  • Create a What To Wear board on Pinterest with examples from your own past shoots – and other inspirational images!
  • Make all pre-shoot messaging affirming and upbeat. Instead of, “Reminder: your session is scheduled for Saturday at 10am,” email, “I’m so excited to photograph you this Saturday at 10am! We’re going to have a lot of fun making photographs together!”
  • Provide a Love List of recommended area vendors who can offer hair and makeup services if your client is interested in pampering herself pre-session. Many salons offer a simple “blow-out” (hair styling) at an affordable rate. See if there’s a DryBar in your city! 

Drop the Obsession with "Pretty" Portrait Photography: Color diptych of young brunette woman walking alonng a cobblestone street in knee socks and a navy sweater. Photographed by Ty Pentecost.
Photos by Ty Pentecost Photography

Every Feeling Counts

No matter what you’ve envisioned, sometimes a portrait photography session simply takes on a life of its own. Perhaps the client’s energy isn’t what you expected, or she isn’t as relaxed as you’d hoped. It’s up to you to embrace the mood before you and find the magic in it.

Help your client breathe through her nerves, and don’t hesitate to make a few photographs that capture that energy. Place her in poses that are comfortable and relaxing. Enable an environment that isn’t straining or stressful, and you’ll begin to see her respond to your comfort-level with the experience.

Drop the Obsession with "Pretty" Portrait Photography: Color diptych of young brunette woman outside. In one close-up image she holds a leaf in front of her face. In the other photo she extends her arms around a low tree branch. Photographed by Ty Pentecos
Photos by Ty Pentecost Photography

Feedback Is Everything

While you’re looking at the back of your camera, admiring your images, your client may be worrying that every shot is bad, her hair looks terrible, her outfit is all wrong, and she was crazy to be photographed in the first place.

Tell her she’s doing a great job! Give her vocal, enthusiastic feedback, with gentle guidance as-needed.

“I talk a lot from behind the camera, giving positive feedback. I’ve found this to be a real game changer as my subject starts to relax and feel beautiful. The women I photograph walk away feeling like they experienced more than just having pretty pictures taken.” – TY PENTECOST

Drop the Obsession with "Pretty" Portrait Photography: Color diptych of young brunette woman on a bridge wearingn a denim-and-cloth jacket. Photographed by Ty Pentecost.
Photos by Ty Pentecost Photography

Carry this feed back through to the final delivery of the photographs. It’s not self-aggrandizing to tell your client how much you love her photographs! Go ahead and set her up for excitement!

Create a ShootProof Mobile App from a selection of your favorite photos from this session, and surprise your client with this on-the-go portfolio!

Learn more and get a demo Mobile App!

Drop the Obsession with "Pretty" Portrait Photography: Color portrait diptych of younng brunette woman wearing a white blouse and navy cardigan outside. Photographed by Ty Pentecost.
Photos by Ty Pentecost Photography


Drop the Obsession with "Pretty" Portrait Photography
Portrait of Crystal Anne

Stay Connected

Columbia-born photographer Crystal Anne photographs people and their stories, but she holds a special place in her heart for portrait photography of women, curating their stories at Release the Women.

“In everything I do, I try to stay connected to the present moment, which allows me to clearly see what matters most. It allows me fully appreciate the beauty and power in myself and in those around me. I also try to help my models connect to the present moment instead of the façade or spectacle of a photoshoot.” – CRYSTAL ANNE 

Drop the Obsession with "Pretty" Portrait Photography: Woman reclines back against a sand-colored brick wall, one hand behind her head, a streak of sunlight illuminating her face. Photographed by Crystal Anne Photography.
Photo by Crystal Anne Photography

Respect Their Boundaries

You’re not a paparazzi. And that’s fantastic, because it means you don’t have to make people angry or upset to pursue meaningful portrait photography.

Make it clear to your clients that you respect their boundaries above all.

  • DO encourage them to relax. DON’T coerce them into doing something they don’t want to do. No means no.
  • DO invite them to share their story. DON’T push them to reveal details they’re not comfortable discussing.
  • DO share some of your own story, so the exchange is equitable. DON’T make the session all about yourself.

Drop the Obsession with "Pretty" Portrait Photography
Photo by Crystal Anne Photography

“When I photographed a group of refugee artisan women for a feature, they were all extremely uncomfortable that I walked in with a camera. I had to assure them that I respected their boundaries, and find a way to creatively portray their voices without taking any actual portraits of their faces. They were comfortable with me photographing their hands, and this gave me room to capture the passion they put into their work. The result is extremely special to me.” – CRYSTAL ANNE

The portrait photography experience must be comfortable for both you, the photographer, and the person or people you photograph. If your clients leave their session feeling awkward or anxious, those emotions will color every aspect of their experience, even through to their ultimate viewing of their images.

Drop the Obsession with "Pretty" Portrait Photography: Diptych of two women. On the left, a woman stands against a wall painted with a sunshine, holding a blue ukulele. Onn the right, a woman dances freely in her own back yard. Photographed by Crystal Anne
Photos by Crystal Anne Photography

Visualize Each Portrait Photography Session With Your Client

“After interviewing one woman for my blog, I asked her do contemporary dance in the forest. It was so sacred. There wasn’t any music. It was just Simone, dancing to the sounds of the quiet forest. That allowed me to capture the power, grace, and beauty of her true self.” – CRYSTAL ANNE

Share your vision for an emotionally intimate session before you arrive with your camera. Prepare your clients with carefully-crafted website messaging, email communication, and a well-curated portfolio. Show your heart and reveal your own values, and your clients will feel at ease revealing theirs.

Drop the Obsession with "Pretty" Portrait Photography: Windblown woman stands on a mountainside, photographed by Crystal Anne Photography.
Photo by Crystal Anne Photography


Focus On What Matters Most

“For me, to focus on what matters most means to uplift, empower, and love the community around me.” – CRYSTAL ANNE

How do you make meaningful portraits – portraits that are more than just “pretty”?

Share your thoughts below!


Written by: ANNE SIMONE | Featuring: MAE B. PHOTO with model JANEL LILES and makeup artist NATALIE COLWELL | Also featuring: TY PENTECOST PHOTOGRAPHY | Also featuring: CRYSTAL ANNE PHOTOGRAPHY | Images prepped with: FUNDY DESIGNER


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