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The dos and don'ts of a headshot.

This is the blunt list. Your headshot is working while you sleep, on profiles and bios and business cards you have forgotten you are on, making a first impression you are not there to manage. Here is what makes one good, what quietly ruins one, and the handful of rules I would enforce everywhere if anybody let me.

By Annie Watson · Naples, Florida · Updated September 2026
Man in a light blue shirt and dark tie, seated and smiling, dark gray backdrop, photographed by Annie Watson in her Naples studio
The Short Answer

The dos: hire someone who will coach you, decide what the photo is for before you shoot it, plan your wardrobe in advance, sort your grooming a few days out, get properly lit, let yourself be directed, and use a picture that looks like you today.

The don'ts: no selfies, no blurry or badly lit files, no group photos with someone cropped off, no party pictures, no sunglasses or heavy filters, no blank profile picture, and nothing so old that meeting you in person plays as a correction.

What actually makes a headshot good.

Four things decide whether a headshot works, and only one of them involves a camera.

  • Light. Good light shapes a face and flatters it. Bad light flattens it, or carves shadows into it, and no amount of editing puts that back.
  • Wardrobe you planned. Clothes that fit, in colors that stay quiet, chosen beforehand rather than grabbed on the way out of the house.
  • Grooming that looks like you on a good day. Not a transformation. A haircut that has settled, facial hair the shape you actually keep it, hair and makeup that hold up under studio light.
  • Direction. Somebody telling you where your chin, your shoulders and your hands go, so the pose looks natural instead of endured.

Get those four right and almost any competent camera will do the job. Get them wrong and the most expensive equipment in the county will still hand you a photograph you quietly dislike and use anyway.

The dos, in order.

Roughly in the order they happen.

  • Do hire someone who will coach you. The photographer's job is not owning a camera. It is seeing what your face is doing and telling you how to fix it.
  • Do decide what the photo is for before you book. A firm bio, a profile, a printed program, a whole company. The use decides the crop, the wardrobe and the mood.
  • Do plan your wardrobe with the photographer beforehand, not by yourself in a hurry.
  • Do bring options. Several tops and a jacket give you several finished looks out of one sitting.
  • Do sort your grooming a few days out rather than the same morning. A fresh haircut needs a little time to look like yours again.
  • Do wear what you actually wear. The picture is a promise about who walks through the door.
  • Do get properly lit, which in practice means a studio rather than a window and a hopeful phone.
  • Do use a current photo. It is the rule I repeat most and the one ignored most.
  • Do let yourself be directed. Guided posing is not a gimmick. It is the difference between a photo of a person and a photo of a person waiting for it to be over.

The don'ts, in order.

Now the ones that quietly cost you.

  • Do not use a selfie. Arm's length distorts a face, the angle is almost always wrong, and everybody can tell.
  • Do not use a blurry photo. Softness reads as carelessness, and it is the one flaw no editing rescues.
  • Do not use a picture from a party. The light is bad, the expression is looser than you remember, and there is usually a glass in the corner of the frame.
  • Do not crop somebody else out. The stray shoulder, the hand on your arm, the half a face at the edge. It always shows.
  • Do not use a photo where the color has gone wrong. Nobody is genuinely orange, or green, or the shade of a boiled lobster.
  • Do not leave your profile picture blank. An empty circle reads as evasive, and people draw conclusions you would not have chosen for yourself.
  • Do not hide behind sunglasses, a low hat, a hand or a heavy filter. Whatever you meant, the message received is that you would rather not be seen.
  • Do not let a stock background do your talking. A skyline you have never stood in front of adds nothing to you.
  • Do not use an old photo. If somebody has to recalibrate when they meet you, the picture cost you the exact thing it was supposed to buy.

Every one of those is the same mistake in different clothes: treating the photo as an afterthought when it is the first thing anyone sees.

Why a professional, and not your phone.

The honest case for hiring somebody is not that your phone is bad. It is that you cannot see yourself.

You cannot tell from behind the camera that your chin has dropped, that one shoulder crept up, that your jaw has locked, or that the light coming past you is drawing a line down one cheek. Somebody standing three feet away sees all of it and fixes it in a sentence. That is what you are hiring: judgment, in real time, about a face you have never once looked at from the outside.

Then there is light, which is a craft rather than a setting, and retouching, which should be done by hand and done lightly. A hand retouched file still looks like skin. An automatic one looks like a mannequin who owes you money.

And there is the part nobody advertises: being talked through it. Most people arrive convinced they are not photogenic. They are almost always just undirected. The long version of how a sitting runs is in the guide to professional headshots, and the mechanics are in how to pose for photos. I make these headshots in my private Naples studio, and people drive in from across Collier and Lee counties for them. If you are coming from Ave Maria, plan on about 45 to 50 minutes.

The rule nobody likes: current beats flattering.

This is the rule people like least, so let me put it plainly. A current photograph that is merely good beats an old photograph that is wonderful.

The purpose of a headshot is recognition and trust, and both break the moment there is a gap between the picture and the person. Somebody who has looked at your photo all week and then meets you spends the first two minutes adjusting. They do it silently, and the adjustment is never in your favor. It is a small deficit, but you opened the conversation with it.

The signs that yours has expired are not subtle: different hair, different glasses, a beard that came and went, a collar you can date on sight. If you find yourself explaining the photo, replace the photo.

The fix is not complicated. Book the sitting, bring the looks you actually wear now, and then replace the picture everywhere it lives on the same afternoon: the profile, the company bio, the conference program that still has the old one. Your LinkedIn headshots are a sensible place to start, because that is the picture that travels furthest.

Variety, and where the wardrobe rules live.

One more thing my original list got right: bring a variety.

A single shirt gives you a single photograph. Bring options, and one sitting gives you several finished looks that you will need sooner than you expect. And make sure the trousers go with the tops, in case a wider frame turns up.

I am deliberately not writing out the full wardrobe rules here, because they have a guide of their own. What to wear for headshots covers color, necklines, fit, patterns, glasses and jewelry in the detail they deserve. The short version: solids, good fit, quiet colors, bring a jacket.

And a note on scope, because these rules are not universal. A personal brand session for entrepreneurs wants more of your real life in the frame, not less. Dating photos follow almost the opposite instincts, warmer and looser and far less corporate. And a personal portrait, like boudoir for Marco Island clients, is a different job altogether. Match the rules to the picture's purpose, or the picture ends up in the wrong room.

Key Takeaways
  • Light, planned wardrobe, real grooming and actual direction decide a headshot; the camera is the least interesting part of it.
  • Hire somebody who will coach you through the pose, because you cannot see what your own face is doing from behind it.
  • No selfies, no blurry files, no party pictures, no cropped group shots and never a blank profile picture.
  • A current photograph that is merely good beats an old one that is wonderful, every single time.
  • Bring several tops and a jacket, so one sitting produces more than one finished look.
Next Step

Every rule here comes down to one.

Get photographed on purpose, by somebody who will tell you what to do with your hands, and then actually use the picture. That is the whole list. If you want to talk through what yours is for and what it should look like, call me at (239) 319-6171 or send the form and I will answer personally.

Book a Session Call (239) 319-6171
Put It to Work

Sessions this guide points to.

Good to Know

Questions, answered.

Can I keep using my headshot from a few years ago if I have not changed much?
Probably not, and the reason is that you are the worst possible judge of it. You see your face every day, so the change is invisible to you and obvious to everybody else. The test is not whether you like the photo. It is whether a stranger who studied it would pick you out across a room. If you have to think about that for more than a second, it is time.
Is a selfie ever acceptable as a headshot?
Not on anything professional. Arm's length distorts a face, widening whatever sits closest to the lens, and the angle is nearly always looking up or down rather than level. It also reads instantly as a selfie, which tells the reader you did not consider the photo worth arranging. Keep them where they belong and let the working picture be a working picture.
Do I really need professional hair and makeup?
No. Doing your own is completely fine. What helps is going a little more deliberately than an ordinary morning, because makeup reads lighter on camera than it does in a mirror. If you would rather hand it over, I work with several professional stylists who can be arranged for hair and makeup before the shoot, for an added fee. It is a preference, not a requirement.
What am I supposed to do with my hands?
Nothing you have to decide by yourself. That question is exactly what being directed solves. I will tell you where your hands go, how much weight sits on which foot, where your chin belongs and when to breathe out. You do not need to arrive with a plan for your body. You only need to arrive.
Is a headshot worth it if my job is not client facing?
More often than people think. Your face turns up in internal directories, on project pages, in conference programs and beside your name in every message you send. It is also the picture that goes out when something good happens and somebody needs an image quickly. Having a decent one already on hand is a small piece of preparation that pays off at exactly the moment you have no time to arrange it.
Book Your Session

Your best headshot is one session away.

Tell me a little about what you have in mind and I will be in touch personally. Pricing is personal, so the best way to plan is a quick call.

Studio
5400 Yahl St, Naples FL

Prefer to talk? Call (239) 319-6171. I respond personally.