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Ask Sherry: Tips on getting a professional headshot or photo taken

You asked, and I am answering every Friday once I have enough questions!

You can ask any question using the form here.

I’m looking to get my first professional headshot.

Are there any tips, tricks or preparation to take in order to get the best picture?


This question actually pushed me to update my own headshot, and instead of paying for a professional, I used my iPhone XS Max in the bedroom, set the timer, set the Portrait to Studio Light, and the results are INCREDIBLE.

You just need a blank wall, good light coming in (but not direct light on your face, more like side light if possible), and to just experiment.

I took my pictures at about 9 a.m. in the morning, just a few hours after the sun makes it way through my apartment, but isn’t overhead in the sky (noon), which would lessen the ambient light coming in.

I took about 100 shots before I decided on 6 of them, sent them to friends to vet, and they ALL came back with a 100% consensus on which one was perfect.

If you do not have an amazing phone with a great camera on it, you can find a willing friend who does (and offer to do each others’ headshots), and go scout out places to take pictures of each other for… pretty much free.

I also decided to go slightly more casual this time around, and just wore a sweater without any jewellery for the shot. We will see if I keep with this, or wear something more formal next time.

Otherwise, here are my notes on a professional picture


Not many people talk about this, but I am so happy you have decided to take a professional headshot.

I kind of cringe when I see headshots of people with red-eye in the shots, clearly at a party / drunk, or where they look great but are clearly cropped out of another photo with someone else or a group.

Professional photos are your calling card, so to speak.

I have so many tips because I have taken many a bad photo in my day, so while I will say I am by no means a professional photographer, or what have you, but I am sufficiently vain enough to care about a good, yet professional looking shot that says to the world in one look who I am and what I’m about to get done.

This is not the time to try a new ANY thing…

Except.. maybe whitening your teeth. Doesn’t hurt to do a little whitening beforehand, I once took a shot where I had slightly yellow teeth and I CRINGE EACH TIME I LOOK AT THAT SHOT.

So much so, I had new ones done.

(Plus I fixed my one snaggle tooth before as well, and that was a $5000 Invisalign price tag, that one….)


What I mean about not trying any new thing, is to not get a facial, change your skin routine or do anything drastic like dye your hair or get a haircut before the shoot. Facials, for instance, bring out the gunk from your skin and it only really appears after 2 weeks…

Plus, sometimes you can have a bad reaction to a change in your routine and how terrible would it be to break out in a rash before the shot? Horrifying.

As for haircuts and hairstyles, keep it simple and routine, but YOU.

I did my professional headshot and ended up sleeping with my hair tied up, I woke up with curls but it looks fake now that I look at it because my hair is not like that. I should have washed it, let it dry naturally as it always does, and just did a bit of body in the hair, that’s it.


I’ll have to take another photo in about 3 years (my update timeline is every 5 years), and this time I won’t make that mistake.

Keep the makeup natural and yes, wear a little

You may not wear a lot of makeup, but a photo is the time to wear a little, especially if it is going to announce you to the world. Women make more money when they wear a little makeup because they look more professional. I’m sorry, it’s true.

(Don’t just trust me, read this article by The Atlantic: The Makeup Tax Women who wear makeup earn more and are treated better.)

This though?

A little too much for a professional headshot. You don’t need the smoky eyes….

(But she is smizing…)

Do not experiment with makeup either, that goes without saying.

Keep the makeup simple, minimal, and you but better.

At a minimum, I know I’d do foundation, concealer, powder, eyeliner, mascara, blush, and eyebrow penciling in.

That is IT.

Your foundation can be heavier for the shot, but I would actually do your face in what you plan on wearing before the shoot, and have a couple of shots taken of you.

I’d even suggest going into Sephora and stressing you want a no-makeup look and see what they do on you, then going home, or in natural light, and taking pictures to see how you like it.

You will see instantly if the eyeliner you are wearing is too dark or too thick, the makeup you have on makes your face look orange but your neck is white, that sort of thing. Or if you don’t look like you.

Treat it like a wedding day photo of shorts, try out what you plan on wearing, your makeup, take some amateur shots and see whether you are satisfied with how things look.

Wear colours that stand out but don’t compete with you

Now, great colours to wear, are ones that contrast but do not compete with you.

I always browse pictures of people and headshots, and I feel terrible when they don’t look good (the lighting is bad, they are in the shadows), or if what they are wearing is really unflattering — black and white suit makes you look like you are going to a funeral, a better bet is navy blue and white, really…

It sounds trite, but colours like blue (almost all shades), white, grey, green, they are all very stable, responsible colours.

Even better if you have blue eyes, wear blue, and your eyes just pop right off the page!!

Browse what other people wear in their photos, and make notes on what and why you think it looks good.

This for instance, would be a great outfit for a headshot:

Avoid red, orange and pink because no matter how hard you try, when you take a shot with them, the colour does something funny in the camera, and it never looks as beautiful and as vibrant as in real life, due to cameras being unable to capture the TRUE colour of red, orange, etc. Just try taking a picture of a sunset, or a red flower and you’ll see exactly what I mean once you get the shot on your phone.

I am not a fan of black or browns for a photo either because it ends up looking very dark in the shot, blends into the background and depending on your skin tone, washes you out or makes you look like a big dark blob.

My go-to colours are navy blue, white, ivory, cobalt blue, black as a trim / accent on something light.

Minimal jewellery is also key because you don’t want the photo to look dated with those chandelier earrings or that choker necklace that were so in last year, but 3 years later, look out of touch.

Choose an outfit that makes you feel like you rule the world

Go for an outfit that makes you feel comfortable yet powerful. For my shots, I always wear a blazer, either structured or a shawl blazer … I choose white (normally), ivory, or blues that look great in a shot.

Depending on your industry, you can go a little more experimental .. or not.

The best time to take shots (I hope your photographer will tell you) is when the light is not harsh and overhead like at noon. Early morning, later afternoons.. these are all much more flattering times for outdoor, natural light.

Remember, the headshot is just your chest and up. Focus on your chest and up, but if it helps you to wear a great pair of pants or a skirt and some heels to get that smizing happening in your shot, DO IT.

I wore high heels and a suit when I did my professional headshot and even though you don’t see any of it, it made a huge difference.

*Smizing = Smiling with your eyes, a Tyra Banks trick. Look into it.

Take a picture in an environment that is not a boring wall

Or at least if it is a wall, MAKE IT A BRICK WALL WITH SOME INTEREST.

Nothing makes me cry more inside than a picture in front of a blank white wall. It works in some instances, but really, it looks much nicer if you are in an environment, like a greenhouse.

When I lived in Toronto, I went to the Gardens (any of them) or in a park, and I chose spots in front of big leafy plants and trees. To this day, these are still some of my best shots.

Practice your smile in shots beforehand


You need a photo to really assess what it looks like because you look awesome in a mirror, but in a shot, you can really scrutinize it in detail.

Again, practice beforehand.

Your natural, big bubbly smile and laugh may not work for a shot — too much teeth! Eyes are too crinkled!

If you don’t smile, you look strained! Pinched! Tired!

UGH. Can’t win.

(This too, is also too much makeup for a headshot by the way. The rimmed and winged eyeliner is a step too far)

(Models have it tough, trust me…. I have watched enough America’s Next Top Model to attest to feeling their pain)

Try big smiles, medium smiles, closed lip smiles, slightly open lip smiles… and think of something or have music playing that makes you happy so that you have a genuine emotion coming out of the shot.

It is so true that if you feel like you just need to take a picture and get it over with, you can see it in the photo.

You need a shot that makes you just take a deep breath, and then relax into the smile, y’know?

Still have a burning question?

You can ask any question using the form here and all of my previous Ask Sherry posts are here.

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