Headshot Session Prep Guide
The most common question before a headshot session, by a wide margin, is some version of: what should I wear? What should I bring? What should I do?
This page answers those questions directly. It is not a list of generic tips borrowed from wedding photography blogs. Every answer here is specific to this kind of session, this approach, and the clients I work with across Connecticut and New York.
If you have a question that is not answered here, contact me before the session. Let's work together so you can look your best!
What to Wear
The General Principle
A headshot is cropped at the chest. Everything in the frame is there to support your face. Your wardrobe is not the subject. It is the frame.
The question is not "what outfit do I like?" The question is "what outfit puts all the attention on my face and communicates exactly what I want to communicate to the person looking at this image?"
Those are different questions, and the second one is the one that matters here.
For Business and Corporate Clients
Wear the most formal version of your daily work attire. Not the most formal outfit you own. The most formal version of what you actually wear to work.
A useful test: if you knew the CEO was walking in with the board of directors at 10am, what would you wear to the office that day? That outfit.
Avoid anything that draws the eye away from your face:
Busy patterns, fine stripes, plaid, or heavy texture
Bright colors or prints that dominate the frame
Ornamental or novelty stitching on collars and lapels
Distracting or overly large jewelry
Hair that falls across your eyes in the frame
Solid colors in the mid-range of the palette tend to photograph well. Navy, slate, charcoal, burgundy, forest green. Not white (flares under studio light), not black (can flatten against dark backgrounds), not neon.
If you are unsure, bring two options and we will decide together before the session starts.
For Non-Corporate Clients
The calculus shifts when the session is not for a corporate environment. The question becomes: how do you want to be seen by the people you are trying to reach?
A therapist in private practice and a real estate developer and a creative director all need headshots. None of them should look alike. The wardrobe for each should reflect the specific relationship their audience expects.
If you are not sure what to wear for your specific context, that is a good thing to bring up before the session. We can work it out.
Hair and Grooming
Show up to the session the way you would show up to the most important meeting of your professional quarter. That is the standard.
Specific notes:
If you get a fresh haircut, get it 5 to 7 days before the session. Not the day before. A brand-new cut often looks stiff on camera and has not settled into the shape that actually works for you.
Glasses with anti-reflective coating photograph cleanly. Standard lenses pick up glare. If you typically wear glasses, bring them. We will work with the lighting to minimize glare, but anti-reflective coating eliminates the problem entirely.
For clients who wear makeup: bring it with you. I always recommend doing a final touch before we start. Even if you applied it at home, the commute changes things.
For clients who do not typically wear makeup: a light, matte powder or setting spray cuts shine under portrait lighting. It takes 30 seconds and makes a visible difference.
Facial hair should be in the condition you want it to be in for the next year or more. These images will be used for a long time.
What to Bring
At minimum: the outfit you have selected, plus one backup. Do not rely on your first choice being the right one until you see it in front of the camera. It almost always is, but sometimes it is not, and having an option costs nothing.
Beyond that:
Any accessories you are considering (belt, watch, jewelry). Bring them and we can evaluate together.
Your glasses, if you wear them sometimes but not always. We can shoot both looks.
Touch-up kit: powder, lipstick, chapstick, a comb or brush. Whatever your normal touch-up routine requires.
If you are shooting multiple looks for different purposes (LinkedIn vs. speaking engagements vs. company bio), organize each look before you arrive so transitions are quick.
Do not bring an ironing board expectation. If there is a travel crease in your shirt from the commute, I can spot it and we will address it. But arrive as close to ready as possible. The session time is most productive when it is spent on expression and energy, not logistics.
Before the Session
Sleep and Hydration
This is not a beauty lecture. It is a practical observation from a lot of sessions: clients who are rested and hydrated look noticeably better on camera than clients who are not. The eyes read differently. The skin reads differently. The energy reads differently.
The night before matters. The morning of matters. Drink water. Get to the session without rushing.
What to Do the Morning of the Session
Arrive looking the way you want to look in the images. Not halfway there, planning to finish getting ready when you arrive. The session is not a backstage area.
If the session is at your office, allow time before it starts to settle. A back-to-back meeting followed immediately by stepping in front of a camera is not the ideal runway. Even ten minutes to exhale, check your appearance, and shift your attention makes a difference.
Skincare
If you have an active skincare routine, maintain it normally in the days before the session. Do not try a new product, treatment, or procedure the week before. Any reaction or adjustment period will show in the images.
On the day of the session: moisturize. Full stop. Dry skin is harder to retouch and catches light in ways that look uneven. Basic hydration takes care of most of it.
Managing Nerves
Almost everyone is nervous before a headshot session. This is completely normal and it is not a problem.
Being nervous does not produce bad headshots. Being tense and trying to hide that you are nervous sometimes does. The distinction matters.
What works: tell me at the start of the session that you are nervous. I will tell you what to do with your body and your face, step by step, the whole time. You do not need to figure out what to do. That is my job. Your job is to follow the direction and breathe.
What does not work: trying to perform confidence for the camera while holding tension in your shoulders and jaw. I can see it, and more importantly, the camera sees it.
The session is slow and deliberate. We stop and review images together. Nothing is rushed. There is no single moment where everything either works or fails.
On the Day
What to Expect When We Start
The first few frames of any headshot session are almost never the best frames. This is true for every photographer and every subject. The opening minutes are calibration: calibrating the light, calibrating the camera settings, calibrating you to the process.
There is no pressure on the first frame. The session builds. By the time we are 20 minutes in, you will have found your footing and I will have found what works for you specifically.
We will pause and review images together on a laptop before the session ends. If something is not working, we address it before you leave. You will not receive the final images and discover a problem for the first time then.
My Direction During the Session
I direct posture, angle, expression, and energy throughout the session. You do not need to bring a pose. You do not need to know what to do with your face. I will tell you.
What I ask in return: follow the direction, even if it feels unfamiliar. Slight adjustments in chin angle, shoulder position, or the space between your upper teeth and lower lip change what the camera sees in ways that are difficult to perceive without looking at the camera. Trust the direction. Check the results.
Expressions and Energy
A headshot does not ask you to smile. It asks you to communicate.
The expression that works best is specific to the context: who is looking at this image, what relationship do they want to believe is possible with you, and what is the first thing you want them to feel.
An attorney's headshot and a therapist's headshot and a startup founder's headshot are all asking for different things. We figure out yours before the session ends.
One rule that applies across all of them: the best expressions are not performed. They are found. I will know when we have found one.
After the Session
Delivery
Final retouched images are delivered within the week following the session. The exact timeline depends on the scope of the session and the current production queue. I will confirm the delivery window before or at the session.
Delivery is digital, via a private gallery. You can download from there directly. If you need images in a specific format, size, or resolution for a particular platform or print application, let me know before delivery and I will account for it.
Retouching
All delivered images include professional retouching. The standard is: you, on your best skin day, at your current age. Not younger. Not significantly altered. Not airbrushed past recognition.
Retouching that goes beyond that standard is available at an additional cost. That includes composite work or significant graphic modifications.
If you receive your images and want a small additional retouch on a specific detail, reach out within the first week. Light adjustments are handled at no charge. More substantial retouching is available for a fee.
Usage
The images are licensed for your personal and professional use across standard platforms: LinkedIn, company bios, speaking bureau profiles, media kits, personal websites, email signatures, press releases, and similar applications.
Commercial usage beyond personal professional application, including advertising, publication, and licensing, is covered under a separate commercial license. If you have a specific use case, ask before the session and I will make sure it is scoped correctly.
Frequently Asked Questions
How long will my session take?
That depends on you and the goal. Someone who arrives camera-ready, wardrobe selected, groomed, and confident can be done in 10 to 15 minutes. Others benefit from more time: trying multiple outfits, working through a range of expressions, or simply settling in front of the camera. Some clients block out four hours in their calendar, not because the shoot takes that long, but because they do not want pressure from anything scheduled before or after. That instinct is right. There is no prize for finishing quickly.
Should I hire a makeup artist for my session?
For most corporate and professional headshot clients, no. Arrive groomed as you would for the most important meeting of your week, bring touch-up supplies, and that is enough. A matte powder and a clean lip make a visible difference under portrait lighting and require no professional.
For executive portraits, branding sessions, or clients who want a more polished or fashion-forward look, a makeup artist is worth considering. I can provide referrals if you want recommendations.
For team sessions: standardizing makeup approach across a large team creates visual consistency. Worth discussing in the pre-session planning conversation if your organization cares about cohesion across a team portrait set.
Should I get a haircut before my headshot session?
Yes, but schedule it 5 to 7 days before the session, not the day before. A brand-new cut often looks stiff on camera and has not settled into the shape that actually works for you. The haircut you wear every day looks better on camera than the haircut you got yesterday.
Can I bring a friend or colleague?
Yes. Some clients find it easier to settle in front of the camera when someone familiar is in the room. If that is you, bring someone. The one condition: the person in the room should be a calm presence. Someone who jokes around in ways that are hard to recover from, or who provides real-time critiques of expressions as they happen, makes the session harder. If you know that about someone, leave them outside.
What backgrounds do you use?
For on-location sessions, backgrounds are drawn from the environment: architectural elements, clean walls, hallways, exterior facades, lobby spaces. The selection depends on what reads well for your specific context and what is available at your location.
I do not use portable seamless paper backgrounds for most corporate sessions. The context collapse of a bright white seamless against a clear office background is visible in the image and reads as low production value. The environment is the background, chosen deliberately.
If you have a specific background in mind or want to incorporate a recognizable element of your office or workspace, tell me before the session. We can plan around it.
What if I need images in different formats for different platforms?
Different platforms have different requirements. LinkedIn uses a square crop. Speaker bureau profiles sometimes want specific dimensions. Print bios want higher resolution than web applications. Let me know before the session what you are planning to use the images for, and I will deliver files optimized for those applications.
Standard delivery includes high-resolution files suitable for print and web. Specific crops, resizes, or format conversions beyond that are available on request.
Should I update my headshot on a schedule?
Update it when it no longer looks like you. That is the actual rule, and it is simpler than any calendar-based schedule.
The practical markers: significant change in appearance (hair, weight, age), career shift that changes how you want to be perceived, or an image that is more than three to four years old and starting to show it. If a client, colleague, or employer meets you in person and does a visible double-take comparing you to your headshot, it is time.
For clients whose industries put a premium on currency and personal brand, annual or biennial updates are common. For clients in more stable professional contexts, good images last longer.
Can I use the images for advertising?
Standard delivery covers personal and professional use: LinkedIn, bios, media kits, websites, press materials, speaking profiles, and similar non-commercial applications. Advertising and commercial licensing requires a separate conversation and a different fee structure. Bring it up before the session so we can scope it correctly.
What if I hate how I look in photos?
Almost everyone says some version of this before a session. And almost everyone leaves with images they genuinely like. That gap is not luck.
The work of a headshot session is not pointing a camera at someone and hoping for the best. It is direction: posture, angle, expression, energy, the specific micro-adjustments that change what the camera reads. That direction is specific to you. I will tell you what to do throughout the entire session. Your job is to follow it and breathe.
We also review images together during the session, so you are not discovering results for the first time at delivery. If something is not working, we address it before the session ends.
Do you shoot in black and white?
Black and white is available and sometimes the right choice: it strips distraction, it ages well, and for certain industries and contexts it reads with more authority than color. Whether it is right for your images depends on how you intend to use them and what the platforms require.
Most corporate and LinkedIn applications want color. Some industries and personal brands lean toward black and white deliberately. We can deliver both from the same session if you want the option.
I am part of a team that needs headshots. How does that work?
Team sessions are individual sessions run back to back. The challenge with team headshots is that most organizations think of them the way they think of badge photos: fast, functional, interchangeable. That approach produces exactly those results.
I advocate for as much time per person as possible. The practical floor is around 10 to 15 minutes per person. Quality starts to drop below five minutes per person, regardless of what you may hear from photographers who market on volume.
Total session time for a team can range from two hours for a small group to multiple days for large organizations. Logistics for team sessions, including scheduling, location, and sequencing, are handled in the planning conversation before anything is booked.
What does the retouching actually do?
The goal is to make you look like you, on your best skin day, at your current age. Stray hairs that caught the light in a distracting way. Uneven skin tone from overhead office fluorescents. A temporary blemish. Shine that the powder did not fully cut.
What retouching does not do: change the structure of your face, remove features that are part of how you look, or produce an image that makes people double-take when they meet you in person. The image should match the person who shows up to the meeting.
What should I do if my session is outside or in a space with variable light?
On-location sessions in exterior or variable-light environments require more technical flexibility than controlled interior sessions. I bring the lighting equipment necessary to maintain consistency regardless of conditions, but you can help by giving us the best version of the space.
For exterior sessions: avoid reflective surfaces near the shooting area if possible, and check that the area will be accessible and unobstructed at the session time. Outdoor sessions typically have a narrower ideal window, usually early morning or the hour before golden hour. We will discuss timing before the session.
For interior sessions at your office: turning off overhead fluorescent lighting and relying on my kit produces cleaner, warmer, more flattering results than mixing light sources. If you have control over the lighting in the space, we can talk through what to leave on and what to cut.
Can I get a copy of the unretouched images?
No. Unretouched images are working files, not deliverables. Delivering them would be like a tailor handing you a garment before it is pressed and finished. The image you receive is the image as it is meant to look. The raw file is not a meaningful intermediate product for the client.
Let’s start a conversation
Tell me a little about where you are and where you’re trying to go.
There are no wrong answers here.
This is the beginning of a conversation, not an application.