What to Wear to Your Headshot Session | Boston Branding Photographer

Woman standing against a mural during her headshot session in Massachusetts. Tips on what to wear for your headshot photo shoot in the Greater Boston area.

You might be thinking of your headshot as a utilitarian photo primarily used to help people identify you, but the truth is that a headshot can say so much more than that!

I always try to infuse these portraits with a little bit of personality, so that your photo tells people something about you. Of course, part of that includes choosing an outfit that works well on camera!

I love helping my clients showcase their personalities while remaining professional, and I’m sharing all of my best tips here:

Choose clothing that fits perfectly

You know when something fits you just right. It should be just the right width in the shoulders and fit close to your body. Avoid baggy shirts and dresses with a lot of draping.

If you aren’t sure whether something fits nicely, ask your most fashionable friend for feedback.

Beautiful Boston corporate employee headshot photograph. Wear great fitting clothes for your headshots.

Go for contrast

When choosing colors, opt for colors that help your skin tone to stand out, avoiding anything that might wash you out. If you have fair skin, choose deeper colors. If you have dark skin tones, look for lighter colors.

You’ll want to avoid stark white shirts and fluorescent items. If you choose to wear all black, make sure you’re not hugging any furry animals before your photos! Lint rolling is highly recommended.


Keep it simple

When it comes to headshots, we want your face to stand out—not your outfit. Avoid patterns that make your eyes swim, like checkered shirts, houndstooth, busy patterns or tiny stripes.

A word about glasses

If you wear glasses every day, then by all means, wear them for your headshots. Just be aware that lens glare is a very real thing, so we may have to spend some time making sure you’re at just the right angle. If you have anti-glare coating on a pair of glasses, bring those.

Wear glasses to your headshot photography session, but make sure they have an anti-glare coating. No coating? That’s fine, but we may need to spend some time making sure you’re at the perfect angle to avoid glare.

Be aware of your undergarments

Your undergarments are just as important as the rest of your outfit! I suggest trying everything on together to make sure that your undergarments aren’t stealing the show.

For women, make sure that your bra straps aren’t showing and that your bra isn’t creating any visible lines beneath your top or dress.

Gentlemen, if you wear an undershirt it’s best to choose a v-neck with sleeves so that it isn’t visible.


Feel free to wear or bring some accessories that hint at your character! When it comes to jewelry, I recommend leaving necklaces at home because they can cut you off in awkward ways or get cropped oddly. Instead, choose a favorite pair of earrings (for earring wearing individuals) or a great tie (for the tie wearing crowd).


Still don’t know where to begin?

If you still aren’t sure what to wear, here are a few of my go-to outfit recommendations:

A simple wrap dress with earrings

A great fitting button down shirt (layered with sweater or blazer—optional)

A solid colored sweater

A suiting dress (with appropriate undergarments and/or a blazer or sleeves—sleeveless dresses can present all kinds of problems when you’re seated)


Let’s talk about grooming

If ever there was a day to look great at work, this is it! Everyone always has questions about hair, so here we go:

  • If you have a short haircut, I recommend getting a trim several days ahead of your headshot session.

  • For long haircuts, if you like to style your hair, please do. I don’t recommend doing anything you haven’t done before, but if you like to straighten or curl your hair for photos, go for it! Remember: hairspray is your friend.

  • Gentlemen, please trim up your facial hair on the day of your session. Use a new razor for a clean shaven face, and trim up your goatee, mustache, beard, and ‘burns if you have ‘em.

Please let me know if you have any questions! I’m looking forward to photographing you soon.