What to Wear to Your Headshot Session: The Real Answer From a Photographer Who Has Seen It All

I have been photographing professionals, entrepreneurs, and executives for over 15 years. And the question I get asked more than any other, before almost every single session, is this:

What should I wear?

The internet will give you the same recycled answer. Solid colors. Avoid patterns. Nothing too trendy. And while that advice is not wrong, it barely scratches the surface of what actually makes a headshot work.

So here is the real answer. From someone who has seen thousands of sessions and knows exactly what the camera loves and what it does not.

DO: Wear solid colors

Solid colors keep the focus exactly where it belongs… on your face. Jewel tones, navy, camel, white, and olive all photograph beautifully. They add depth and dimension to the image without competing with you for attention.

When in doubt, a solid color in a shade that complements your skin tone is always the right call.

DO: Wear a well-fitted blazer or structured layer

A structured jacket or blazer is the single most reliable thing you can put on for a headshot session. It creates clean lines around the shoulders and torso, frames your face, and communicates authority before you say a single word.

It does not have to be formal. It just has to fit well. A blazer that fits is always more powerful than one that is just close enough.

DO: Bring options

Bring a light option and a dark option. Something more polished and something slightly more relaxed. You do not need a full wardrobe to create range in your gallery, a jacket swap can do it entirely.

More options going in means more variety coming out. And a gallery that works across every platform you need to show up on.

SKIP: Busy patterns and large logos

Patterns pull the eye away from your face. And your face is the whole point of a headshot. Busy prints, bold stripes, and large logos all compete for attention in a frame where the only thing that should matter is you.

They also date faster than almost anything else. What feels current now can look noticeably dated in eighteen months.

SKIP: Trendy pieces you will regret in two years

Your headshot should work for you in 2026 and in 2028. Dress for longevity. The pieces that photograph best are almost always the ones that feel timeless rather than of-the-moment.

Think about where this image is going to live. Your LinkedIn. Your website. Your speaking bio. Your press features. You want it to still feel like you two years from now.

SKIP: Making black your only option

I love a black blazer. It photographs beautifully and there is a reason it is a staple. But I see people default to black as their only option all the time and it is a missed opportunity.

Color does something to a photo that black simply cannot. It adds warmth, personality, and dimension in ways that translate even in a still image. Bring the black blazer. And bring the color you keep talking yourself out of. Try both. You will see the difference immediately.

The rule I tell every single client

Wear something that makes you feel like the most capable version of yourself.

This is the one that matters most and the one nobody talks about. The camera picks up how you feel in your clothes. When you feel confident and ready, it shows in every single frame. When you feel slightly off, that shows too.

You can follow every style guideline perfectly and still walk in wearing something that does not feel like you. The best headshot is always the one where the clothes and the person match completely.

Dress like you already know how this ends.

Ready to book your headshot session in Naperville or Chicago?

The April 15th Headshot Mini Marathon at Studio 25 Naperville includes professional hair and makeup touch-ups, expert guidance throughout, same-day image selection, and final images delivered within 48 hours.

You show up. I handle everything else.

Reach out to book your spot before they are gone.