Executive Headshots
Thoughtfully Crafted.
Steve Simon is a Westchester–based photographer with decades of experience photographing people in real situations. His headshot sessions are calm, unhurried, and focused on helping you feel at ease so the photograph feels natural, confident, and true to who you are.
PROFESSIONAL HEADSHOTS IN WESTCHESTER, CONNECTICUT & NEW YORK CITY
My headshot sessions are designed to create photographs that feel natural, professional, and believable—images that work across platforms and over time. We focus on expression, posture, and presence rather than posing or tricks, working steadily until the photograph feels right.
Most people don’t love being photographed. That’s normal. My job is to make the process easy. I guide when it helps, step back when it doesn’t, and keep things relaxed and unforced. No pressure. You don’t have to perform. You don’t have to think about how you look.
I photograph headshots from the chest up, keeping the framing clean and consistent while allowing room for subtle variation. Throughout the session, I make small adjustments in posture and expression, helping you look confident and at ease without feeling staged. You’re encouraged to bring a few clothing options so we can vary tone and use—if it’s there, we can work with it.
Sessions are unhurried and shaped around what you need. Some people need one strong image. Others want a range of options for different uses. We let the work dictate the pace.
As we shoot, we review images together in real time. This keeps the session focused and helps us move toward stronger results without second-guessing. We take our time and keep working until the camera fades away and what comes through feels natural, confident, and unmistakably you—on your best day.
After the session, you’ll receive a private proof gallery to make your selections. Retouching is natural and restrained, designed to clean up distractions while keeping you looking like yourself. Final images are delivered ready for professional use across LinkedIn, websites, press, and corporate profiles.
BOOK A HEADSHOT SESSION WITH STEVE SIMON
The Essential Headshot
A guided session focused on creating one strong photograph that feels natural and professional. We work through expression and posture at a steady pace, reviewing images together in real time so we can make small adjustments and keep the session moving in the right direction.
Includes:
A relaxed, guided headshot session
Multiple frames and looks during the shoot
A private proof gallery of at least 20 images
One fully retouched final image
This option is a good fit if you need a single headshot for LinkedIn, a website, or press use.
Additional images may be added after the session at a cost of $150 per retouched headshot.
On-Location Option
Prefer to be photographed at your home or office? I travel anywhere in Westchester for an additional $150. Locations in Connecticut or New York City may require an additional fee depending on distance. The session experience stays the same—only the setting changes.
$450
The Signature Headshot
The same relaxed session, with more finished images to choose from. This option offers flexibility for different expressions, crops, and uses—without the need to reshoot. We work steadily, reviewing images together in real time making small adjustments as we go so everything stays on track.
Includes:
A relaxed, guided headshot session
Multiple frames and looks during the shoot
A private proof gallery of at least 20 images
Five fully retouched final images & One Black and White Version
Most clients choose this for the variety it offers.
Additional images may be added after the session at a cost of $150 per retouched headshot.
On-Location Option
Prefer to be photographed at your home or office? I travel anywhere in Westchester for an additional $150. Locations in Connecticut or New York City may require an additional fee depending on distance. The session experience stays the same—only the setting changes.
$700
Essential Session Examples
Most people will encounter your photograph before they meet you. It lives on LinkedIn, company websites, press releases, social profiles, and email signatures. Whether you like it or not, it shapes perception. A strong headshot communicates confidence and approachability without trying too hard. It builds trust quickly and signals that you take your work—and the people you connect with—seriously.
WHAT TO WEAR
The most important rule applies to everyone: wear clothes you love and feel good in. If you’re uncomfortable, it will show.
Bring options. Different colors, cuts, and layers give us flexibility and allow us to create variety without slowing the session down. Solid colors and clean lines tend to photograph best.
If you’re unsure about something, bring it. If it’s there, we can work with it.
MEN
Jackets, shirts, and optional tie combinations work well. A more formal and more relaxed look gives us options for different uses. Keep patterns subtle. Jewelry should be simple or skipped entirely. If you wear glasses and have more than one pair, bring them so we can see what works best with the light.
Facial hair is welcome. Come as you normally wear it. If you’d like to try a cleaner look or different levels of stubble, bring your grooming tools and we can make adjustments during the session. Makeup is not necessary. Light grooming can be arranged if desired, though professional retouching usually takes care of minor skin distractions.
WOMEN
Blouses, dresses, and jackets photograph well, especially when you bring a few options that vary neckline, structure, or tone. Simple layers add flexibility and keep the session moving.
Jewelry should be minimal—small earrings and simple necklaces tend to work best. Anything large or dangling often pulls attention away from your face.
Makeup is not required but a light, natural look works best, and professional retouching will handle any small distractions.
Hair should be styled the way you like to wear it on a good day.
