Dear reader,
You may have noticed there was no letter last week. Life got busy in the ordinary ways it sometimes does, and I’d rather skip a week than send you something half-finished. So, on to this week’s topic.
The question I get asked most before a headshot session isn’t about lighting, location or how long it’ll take. It’s “what should I wear?” Usually asked a little nervously, often the night before.
Here’s the honest answer, and it’s simpler than most people expect.
Wear what you’d wear to meet an important client
Your headshot is the version of you people meet before they meet you. So dress for that meeting. Not your wedding outfit, and not the jacket you bought for a conference three years ago and haven’t worn since. If you’d feel slightly in costume wearing it to work, it’ll look slightly like a costume in the photo.
The goal is for someone to meet you in person and think, “yes, that’s them.”
Solid colours beat patterns, every time
Fine stripes, small checks and herringbone can create a shimmering effect on camera that the eye doesn’t see in the mirror. Bold prints pull attention away from your face. Logos date quickly.
Solid, mid-tone colours are the safest choice: navy, charcoal, deep green, burgundy, soft blue. They flatter most skin tones and keep the focus where it belongs.
The neckline is most of your outfit
A headshot usually crops somewhere around the chest, so your collar or neckline is doing almost all the work. A clean collar, a structured jacket or a well-fitting crew or V neck reads well. A collar that’s crumpled, too big, or sitting unevenly will show more than you’d think.
A jacket or cardigan over a shirt adds a bit of depth and structure, even if you take it off for a few frames later.
Fit matters more than the label
An inexpensive shirt that fits and has been properly ironed will look better than an expensive one that’s pulling at the buttons or bunching at the shoulders. Iron it the night before, hang it up, and bring a lint roller. Dark fabrics in particular pick up every bit of dust and pet hair, and the camera finds all of it.
If you wear glasses, wear them
If people know you with glasses, your headshot should have them too. The only real challenge is reflections, and I learned this one the hard way myself. When I recently filmed a short video for my own website, I watched the playback and saw the window reflected straight across both lenses. I’d been so focused on what I was saying that I hadn’t noticed where the light was coming from.
In a photography session, that’s my job to manage, not yours. A small change to the angle of your head or the position of the light usually solves it. If you’re getting new glasses anyway, an anti-reflective coating helps too.
A few small things that make a big difference
- Haircuts: a week before, not the day before. It gives things time to settle.
- Shine: a little matte powder takes care of it, for anyone, regardless of whether you’d normally wear makeup.
- Bring options: two or three tops is plenty. We’ll pick together on the day, and it takes the pressure off getting it right in advance.
- Jewellery: keep it simple. Something you wear every day is fine. Something that catches the light will draw the eye.
For teams, consistency matters more than any one outfit
If your whole team is being photographed, the most important decision isn’t what any individual wears. It’s agreeing on a shared standard before the day. Jackets or no jackets. Dark tops or light. Collared or not.
A team page where everyone looks like they belong to the same organisation does more for your credibility than any one perfect photo. I always help set that brief before a team session, because it’s much easier than fixing inconsistency afterwards.
For boards and committees, the brief matters even more
Associations and peak bodies face a version of this that most businesses don’t. Your board might meet in person twice a year. Your directors are volunteers with day jobs, spread across several states. Some will be photographed at your AGM, some will send in a photo taken by a colleague, and one will inevitably supply a cropped wedding photo.
The result is the page every association knows: a board where every portrait has a different background, a different crop and a different level of formality, sitting right next to your annual report.
A short dress brief, sent with the invitation to be photographed, fixes most of this before it starts. It’s not about making volunteers feel policed. It’s about making them look like they belong to the same organisation, because they do.
It’s also worth thinking about your sector’s tone. A peak body that regularly appears in front of government will want something closer to business dress. A community organisation may want to look approachable rather than corporate. Neither is wrong, but your board should all be pitched at the same one.
To make this easier, I’ve put together a free Board Photo Brief: a ready-to-send email for your directors, a one-page dress guide to attach, and a checklist for whoever is coordinating the day.
The short version
Wear something that fits, in a solid colour you feel good in, that you’d happily wear to meet someone important. Bring a backup. Leave the rest to me.
If you’re thinking about updating your own headshot, here’s how I approach executive headshots and portraits.
Until next week,
Brock