Chicago High-End Headshots

Chicago High-End Headshots Headshot Photographer & Facial Expression Coach

Creating Confidence & Approachability 😄

I’ve said this before, and I get to say it again … it’s a privilege to do this work.When Bob Fesmire came into the studi...
02/13/2026

I’ve said this before, and I get to say it again … it’s a privilege to do this work.

When Bob Fesmire came into the studio for headshots and a few casual portraits, what stood out most wasn’t the titles or the résumé.
It was the conversation.

Bob and I connected as dads; both raising two daughters, both navigating the pride, worry, joy, and challenges that come with that role. Those conversations matter. They create space. They create trust.

Yes, Bob is the fifth-generation President & CEO of Ellis Corporation.
But he’s also a musician.

At one point during the session, Bob sat down with his Gibson and just… played.
No cue. No direction. Just a moment unfolding on its own.

Music has a way of doing that; creating space, shifting energy, revealing presence. And not gonna lie … strong Dave Grohl / Foo Fighters vibes. Vocals included.

There’s something about music that does that. It slows things down. It elevates the moment.
This was one of those moments.

At the end of the session, Bob thanked me.
But honestly? I felt like I owed him the thank you; for the trust, the openness, and the willingness to simply be himself.

And really… isn’t that what this is all about?
The most powerful images don’t come from being photographed, they come from feeling seen.

Celebrating Matt Crabtree’s new headshots, and honestly, the person behind them.Matt is one of those people whose authen...
01/30/2026

Celebrating Matt Crabtree’s new headshots, and honestly, the person behind them.

Matt is one of those people whose authenticity shows up before the camera ever comes out. A University of Illinois Urbana-Champaign standout (yes, I’ll admit a little personal bias there—my daughter is a grad student at Illinois), he brings a rare mix of intelligence, humility, and quiet confidence into the room.

His wife, Hayley, an Illinois State University Redbird (full disclosure: ISU alum here 🙋‍♂️), balances him perfectly. Add in the fact that they’re both devoted dog lovers (automatic entry into my good humans category), and recently welcomed their newborn daughter, Charlotte, and you’ve got a pretty special chapter unfolding for this family.

On top of all that, Matt has launched his own firm, Breakaway Advising a name that fits him well. Purposeful, thoughtful, and built on genuinely helping people move forward.

The headshot reflects what’s already there: presence, approachability, and integrity. But more than that, it was simply a pleasure spending time with someone who shows up as himself; no pretense, no performance.

Congrats, Matt. Wishing you continued success in business, fatherhood, and everything in between.

Most slow down during the holidays.For us, it’s the only quiet window to build.What started as a blank canvas has become...
01/08/2026

Most slow down during the holidays.
For us, it’s the only quiet window to build.

What started as a blank canvas has become a more refined, modern studio; designed with one thing in mind: giving clients more ways to show up authentically in their images.

New textures.
Elevated tones.
More background options that feel intentional, polished, and versatile.

These updates aren’t about trends or aesthetics for their own sake. They’re about creating environments that support different personal brands; whether someone needs understated and corporate, warm and approachable, or bold and modern.

The camera captures what’s there.
The space helps set the tone.

Excited to start the year with a studio that better reflects the level of work, and people we serve.

A Fun TwistA few years back, I referred a prospective client to photographer Carl Chandler. Fast-forward … Carl and I fi...
12/12/2025

A Fun Twist

A few years back, I referred a prospective client to photographer Carl Chandler.

Fast-forward … Carl and I finally met in person at a networking event. Always great having a real conversation with another creative; business challenges, workflows, client experiences… and of course, gear. Photographers can talk gear forever. 😂

Then Carl did the bravest thing a photographer can do:
He stepped in front of the camera.

Most of us would rather rebuild a tripod blindfolded than be the one getting photographed, but Carl owned it. He reached out wanting updated images, and we created a set of confident, authentic looks for his professional branding.

While Chicago High-End Headshots focuses on business professionals, entrepreneurs, and executives…
Carl is the guy you want if you’re in the acting world. He knows the industry, understands casting expectations, and serves the acting community extremely well.

Had a blast “capturing” a fellow photographer… safely, gently, and only with a Canon USA. 😉

A first for me — a Father & Son headshot session.Still not sure who’s influencing who…Pete’s seasoned style or Ethan’s r...
12/04/2025

A first for me — a Father & Son headshot session.

Still not sure who’s influencing who…
Pete’s seasoned style or Ethan’s rising-level confidence.
All I know is they walked in looking like they planned it — and absolutely owned the room.

And when it comes to professional branding?
These two didn’t just show up.
They set the bar.

Honored to photograph them both and capture a moment where confidence clearly runs in the family.

Who do you think was the trendsetter here — Pete or Ethan?

When I photograph people, I often think about what they stand for; the impact they’re making in the world.This one hits ...
11/13/2025

When I photograph people, I often think about what they stand for; the impact they’re making in the world.

This one hits close to home.
Grace Tolentino, Founder & Director of Core Psychotherapy Center , leads a team of compassionate professionals who stand on the front lines of mental health; guiding, supporting, and healing others every single day.

As someone who has become a strong advocate for mental health myself, photographing Grace carried extra meaning. Her quiet strength and empathy come through in every expression, the kind of presence that makes people feel seen, understood, and safe.

To Grace and her team, thank you for the vital work you do. You are true warriors in a field that changes lives every single day.

📸 Headshot created at Chicago High-End Headshots

Confidence doesn’t have to shout to be seen.Sometimes, it’s in the way someone carries themselves, and that’s exactly wh...
10/30/2025

Confidence doesn’t have to shout to be seen.

Sometimes, it’s in the way someone carries themselves, and that’s exactly what Katelyn Hammond Davis brought to her session.

Every once in a while, someone walks into the studio who reminds me why I love what I do; that was Katelyn.

She’s spent more than a decade blending her background in microbiology with a gift for leadership, helping teams bring safe, innovative products to life. What stood out most was her energy, calm confidence, genuine warmth, and that quiet spark of curiosity you can’t fake.

Katelyn wanted headshots that captured her executive presence and confidence, not just a polished image, but one that truly shows who she is. Through our facial expression coaching, we refined the subtle cues; confident eyes, relaxed posture, approachable energy, that communicate strength and authenticity in one frame.

Beyond her career success, Katelyn has a grounded, genuine way about her; the kind that reminds you real leadership doesn’t have to be loud to be powerful. Her new headshots capture exactly that energy.

Chicago High-End Headshots | www.chicagohighendheadshots.com
Transforming how professionals see themselves, and how the world sees them.

The Moment Everything ShiftsThere’s always a moment when it happens.The nervous laugh fades. The shoulders drop. The ten...
10/17/2025

The Moment Everything Shifts

There’s always a moment when it happens.

The nervous laugh fades. The shoulders drop. The tension finally lets go.

In that quiet second, confidence shows up; not the kind you fake, but the kind that’s been there all along.

That’s the moment I wait for. The one frame where someone stops trying to look confident… and just is.

🔥 This isn’t about a picture. It’s about presence.

Learn More: www.chicagohighendheadshots.com

Big thank you to Brandon Cork, for connecting me with Zach Neff, Area Loyalty Manager at IKEA.Funny enough, we’ve got a ...
09/24/2025

Big thank you to Brandon Cork, for connecting me with Zach Neff, Area Loyalty Manager at IKEA.

Funny enough, we’ve got a few IKEA pieces in the studio. I thought about pointing them out; turns out I didn’t need to. Within seconds, Zach was naming each model like a proud parent introducing their kids.

But what stood out even more during the session was Zach himself. As we got to talking, we realized our paths had crossed before, and we connected on some shared principles in life, and in being dads.

That’s what I love about this work: when you create space for someone to settle in, the real person emerges.

This transformation isn’t just a sharper photo, it’s the Zach I met in the studio, and the Zach others will meet.

👉 Here’s his new headshot transformation.

Be seen as the leader you are.When George Stephen stepped into the studio, he brought with him a quiet strength; the kin...
09/09/2025

Be seen as the leader you are.

When George Stephen stepped into the studio, he brought with him a quiet strength; the kind that comes from years of helping business owners find clarity, control, and peace of mind in their finances.

Referred by the ever-thoughtful Michael Ziffra (thank you!), George has spent decades guiding companies through their toughest challenges. His superpower? Creating financial systems that give leaders the freedom to focus on what really drives their business, while still keeping a firm hand on the wheel.

There’s always a moment where things shift from ‘taking a headshot’ to owning the room. With George, it came during a story, a laugh, and then that look of presence and purpose. The "Headshot" is created; that’s what made the frame.

➡️ That’s what a powerful headshot does.
It doesn’t just show what you look like, it shows who you are as a leader.

If you’re ready to stop playing small with your image, if you want people to see the experience, trust, and warmth you bring to the table, I’d love to help you step into that spotlight.

📸 Let’s create something that feels like you ... only even better.

Recently, I had the privilege of bringing our studio experience on the road for an on-location group headshot session.Th...
08/28/2025

Recently, I had the privilege of bringing our studio experience on the road for an on-location group headshot session.

There’s something uniquely special about photographing professionals in their own environment; their office, their team setting, their space. The energy is different. People feel at ease, surrounded by colleagues, and that comfort translates into stronger, more authentic expressions on camera.

Our process is designed to make it seamless:

We set up a fully professional lighting environment on site.
Each person receives quick, focused coaching to bring out confidence and approachability. Images are reviewed and selected right away, so no one is left guessing.

What I love most is how these sessions turn into moments of connection, coworkers stepping in and out, supporting each other, laughing, and realizing that professional headshots don’t have to feel stiff or transactional. Instead, it becomes part of their company culture and brand identity.

That’s the magic of group headshots: they’re not just photos; they’re a shared experience that helps teams present themselves as the professionals they already are.

📸 Curious about how on-location headshots could elevate your team’s brand? Let’s talk.

Self-Conscious on Camera? You’re Not AloneIf being in front of the camera makes you uncomfortable, you’re in good compan...
08/21/2025

Self-Conscious on Camera? You’re Not Alone

If being in front of the camera makes you uncomfortable, you’re in good company.

We specialize in helping professionals feel confident on camera, even if they’ve never liked a photo of themselves before. Through expert facial expression coaching and posture guidance, we help you show up with natural confidence and approachability.

✨ You don’t need to be photogenic. You just need to be coached.

Book your session and see the difference coaching makes.
www.chicagohighendheadshots.com

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