What Makes a Great Business Headshot?

You know, people ask me sometimes what makes a great business headshot. And usually what they’re expecting me to say is something about lighting or lenses or backdrops. And of course those things really do matter, but they’re not what makes a headshot great.

For me, a great headshot is about presence. It’s about that moment when the real person shows up — when you feel like someone is actually looking back at you through the photo.

It’s a hard thing to define, but it’s easy to recognize when you see it. There’s this sense of authenticity. The person feels relaxed, grounded, there.

I sometimes think about old 19th-century portraits. So many of them feel very formal, very stylized. You can admire them, but you can’t really reach the person. But then you look at  something like Robert Cornelius’s early self-portrait — one of the first photographs ever made — and there’s this uncanny feeling of connection. He’s right there, from nearly two centuries ago, and yet you feel like you could talk to him. That’s what I’m looking for when I shoot a headshot. That sense of presence that bridges the gap between the person and the viewer.

And I think this sense of presence matters because of who’s going to be looking at the photo.

For a business headshot, that viewer is often a client, a colleague, a recruiter, maybe even someone making a hiring decision. The more that person on the other end feels like they’re looking at someone present, the easier it is for them to imagine working with you, feeling comfortable with you, trusting you.

It makes you seem approachable, genuine — like a real human being, not just a polished image. That’s why I chase that sense of presence. Because it’s not just about making someone look good; it’s about helping them connect with whoever’s on the other side of the screen.

Now, how you get to that moment really depends on the person in front of you. I’ve learned to adapt the way I communicate based on who I’m photographing.

If I’m working with someone who’s imaginative or expressive, like an artist or a musician, I might talk in more emotional terms: “Think about someone you admire walking into the room,” or “Imagine you’ve just heard good news.” They understand that language.

But if someone’s more analytical, I’ll explain things in a more literal way: “Turn your head this way so the light catches your eyes,” or “Let’s shift your weight so the posture feels more open.”

Either way, the point is to make a connection — to give them a glimpse of the process. Because people find things they don’t understand intimidating. If I can take away some of that mystery, they relax. And when they relax, the real person starts to appear.

Of course, it doesn’t always go that smoothly. Some people really hate having their picture taken. They come in tense, or guarded, and sometimes no matter what you do, that guard never fully comes down.

And that’s okay. In those situations, I focus on what is within my control: the lighting, the composition, the technical side of things. I’ll go for a neutral but dignified expression, something composed, professional.

I never force someone to smile or push them past what they’re willing to give. Instead, I frame it as collaboration. I might say, “The attitude we bring to this session will shape the photos we end up with. We’re working together to make a good photo.” That way, it’s not me versus them, it’s us making something together.

There’s something strange about seeing someone through a viewfinder in real time versus seeing them in a captured image, even if it’s the same scene. They feel different.

It took me years to start recognizing that intangible something while it was happening — that moment when everything lines up and the expression just feels right. It’s kind of like realizing you’re in a great moment in life while it’s happening, instead of only appreciating it in hindsight. That awareness takes time to develop.

And it’s not something you can always explain. It’s a feeling, almost like the photo has already happened and you’re just catching up to it.

I think that ability comes from two things in equal measure: experience and confidence. Once you’ve built the technical foundation — lighting, exposure, posing — you stop worrying about the mechanics. You stop second-guessing yourself. And once that self-doubt quiets down, you can finally pay attention to the person in front of you, see them clearly, and help them see themselves the same way.

What to wear for a Business Headshot

Here’s what I’ve learned about dressing for a headshot session after thirty years of putting people in front of a lens.

Solid colors are almost always the right call

A solid-color top reads cleanly on camera and keeps the focus where it belongs — on your face. Jewel tones tend to photograph especially well: deep blues, burgundy, forest green, charcoal. Classic gray is reliable. Navy is almost universally flattering.

What to avoid: loud patterns, narrow stripes, and anything with a tight geometric print. These can create a moiré effect on camera — an unpleasant visual shimmer that is difficult to fix. Logos and busy graphics are also worth leaving at home, unless your logo or graphic is part of your outfit.

Think about contrast

If you have a fair complexion, a very pale top can make you look washed out. If you have a deeper complexion, very dark clothing can make it harder to separate you from a dark background. Neither is a hard rule, but it’s worth keeping in mind when you’re picking between two options.

Fit matters more than fashion

Clothes that fit well photograph better than expensive clothes that don’t. A well-fitted blazer from three years ago will serve you better than a trendy oversized piece that obscures your shoulders. The camera compresses depth, so things that look intentionally relaxed in person can just look ill-fitting in a photo.

For men: a blazer or sport coat almost always improves a headshot, even over a simple shirt. You don’t need a tie unless your industry calls for one. For women: neckline matters — something that frames the face without being distracting. V-necks, crew necks, and simple collars all work well.

Grooming and finishing details

Get your hair cut or styled a few days before the session, not the morning of. Fresh cuts can look a little severe, and you want to look like yourself at your best, not like you just left the barber. Same goes for color treatments.

If you wear glasses, my standard lighting setup usually mitigates glare, but not always, so I’d recommend bringing a pair without lenses if you have them, or planning to shoot both with and without. This is by no means a make or break issue though.

A couple things people forget

First, the collar. Check it in a mirror before you leave the house. It sounds obvious, but a crooked collar or an undershirt showing through a button-down is the kind of thing that nobody notices until they see the photo. Second, necklaces. If you wear one, make sure it’s aligned correctly and the pendant is centered. I do look for these things, but it’s still possible I’ll miss it, especially if I’m doing a lot of back to back team headshots in quick succession. It takes three seconds to fix beforehand, but takes considerably longer in post.

If you have questions about whether something specific will work, feel free to reach out before your session. I’d rather answer a quick email than have you show up in something that doesn’t serve you well.