Your Headshot Prep Guide: Everything to Know Before Your Session

Getting professional headshots can feel wicked intimidating, especially if you are someone who does not love being in front of a camera. Most people feel that way, and that is completely normal. The good news is that a great headshot is more about preparation and the experience than it is about being naturally photogenic.

This guide walks you through everything you need to know before your session. None of it is complicated, and you do not have to get any of it perfect. My job is to make the whole thing easy and even fun. Think of this as a head start so you walk in feeling confident and relaxed.

What to Expect

Let's set expectations up front, because knowing what is coming makes the whole thing easier. The people who get the best headshots are not the most photogenic ones. They are the ones who relax and let the real version of themselves show up. That is our only real goal for the day.

So you do not need to know how to pose, and you do not need to be photogenic. That is what I am here for. I will guide you through everything, from where to put your hands to how to angle your chin, in real time, and you will see the photos on a laptop as we go, so we are working together the whole way. I spent years as a teacher working with nervous people from all over the world, and I bring that same patience to every session. We will talk, we will probably laugh, and you will walk out with photos that look like the most confident, natural version of you. Trust the process, and let me handle the technical part.

Feel comfortable to bring a family member or friend for support. And if you have a child, our studio has lots of toys and activities for them to play with.

What to Wear

I bet your first question is, what do I wear? It's pretty much everyone's first question. Here’s something fun - I give you permission to go shopping for new clothes so the lines are crisp and the colors are bold. Return anything you don't want to keep after the session!

I favor solid colors rather than busy patterns. Tight stripes, small checks, and loud prints can distract from your face. Solid, rich colors keep the attention where it belongs, on you. Choose colors you feel good in. All colors work, so don’t worry about color theory and what photographs well or poorly. We’ll figure it out together as we shoot and can change as much as you’d like. 

Fit matters more than anything. Avoid clothing with excess fabric along the collar and shoulders. A turtleneck can push neck skin up toward the face. A blazer's shoulder seams should rest exactly on the edge of your natural shoulder bone, where your shoulder meets your arm. If you must wear a tie, make sure the knot size is proportional to your collar.

For jewelry, keep it minimal. But also, bring as much as you want so we can play around with different combinations with the outfits that you've brought.

Think about where your headshot will live. A photo for a law firm or executive bio might call for something more formal, like a jacket, while a personal brand or creative profile can be more relaxed, even a hoodie. If you will use the photo for more than one purpose, that is great, because in a session with me you have time to change looks and cover several styles for different audiences.

The best part: you do not have to figure this out alone. If you decide to invite a stylist, Molly stays with us the whole time to help with your outfits and make adjustments. So bring a few options, hang them up, and we will choose together. When in doubt, bring more than you think you need.

Hair, Makeup, and Grooming

Professional hair and makeup with Molly may be included in your session, and she can do as much or as little as you want, whatever makes you feel like yourself. You do not need to arrive camera-ready. You can come in for just touch-ups, or arrive as a blank canvas. You can bring your favorite cosmetic products to be combined with Molly's, or let her pull from her kit of professional products.

If you are planning a haircut, get it at least a few days before

your session rather than the day of, so it has time to settle and look natural. A blow-out can be done the same day or the day before. If you have facial hair, simply groom it the way you normally like it. Come with clean, well-hydrated skin, and if there is any chance your hands will be in the frame, give your nails a quick tidy.

A Note on Glasses

If you wear glasses, bring them, and wear them the way you normally would. Lenses can catch reflections, but my Photoshop skills are excellent, so don't worry if you don't have anti-reflective coating on them. Managing glare is part of my job, and we will get clean shots with your glasses on. If you happen to have multiple pairs, bring them too.

  • "Kevin amazes me every time he works with our organization’s events with hundreds of people and ensures we all look and feel wonderful."

    Francesca Rizzo, Associate Event Manager at Liberty Mutual Insurance

  • "Kevin knows how to bring out genuine expressions of love, happiness, and care in his subjects."

    Sara Kittle, Founder and CEO of One Bead

  • "Best photographer experience. Kevin captured all of the great moments and delivered them to our phones in real time. An incredible experience!"

    Jim Panagas, Founder & Chief Communications Officer

  • "Kevin is so talented and helps bring out the joy in group and individual shots at events!"

    Jaja Chen, Co-Owner/Chief of Strategic Initiatives & Business Partnerships

The Day Before

Keep it simple. Try to get a good night's sleep, and drink plenty of water, because feeling rested genuinely shows up in your eyes and your energy on camera. Lay out your outfit options the night before so the morning is stress-free. That is really all there is to it.

When You Arrive

The studio is at 75 Pleasant Street in Malden, just outside Boston. Please arrive on time so we have the full window together, though there is no need to feel rushed once you are here.

If you are running late, don't rush. Drive safely. Your session reserves up to three hours, and while we rarely need all of it, the time is yours, so there is no pressure and plenty of room to try different looks.

We will start with a quick chat about what you are looking for and how you will use the photos. Then we get to work, and you will see the images on a laptop throughout the session, so we are collaborating in real time. You can see exactly what is working and help steer the shots with me.

After Your Session

When we are done shooting, a few good things still happen. We will look through the images together for a final time, and you will choose your favorites. So that you’re not overwhelmed with decision paralysis from looking at hundreds of photos on your own, I will help you pick the right shot for each place you will use it, whether that is a confident look for your executive bio or something warmer for a different audience your personal brand.

From there, I take care of the retouching. Every image you choose gets natural, professional retouching, so you never have to stress about a stray hair or a tough skin day. You will receive your finished photos soon after, in multiple crops, ready to use everywhere you need them.

Relax and Have Fun

Come as you are, bring your options, and let's make something you are genuinely proud of.

Have a question before your session? Reach out any time, and I will be happy to help.