How to Take Good Headshots (that aren’t stuffy)

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it’s a weird thing when we become professionals, isn’t it? i think so. suddenly that cropped picture of me on linkedIn just isn’t cutting it any more. it’s time to figure out how to take good headshots (and not stuffy ones). the stereotypical corporate ones just aren’t me. since i’m doing more speaking now, conference organizers are requesting a slightly more professional photo than me standing on the beach and one without my dog in it (weird).

i set out to find a balance of how to take good headshots that still encompass who i am, yet are more professional.

how to take fun headshots

hire a professional

as much as you want to be convinced that with the perfect angle from your self-stick, you just might be able to pull it off, you won’t. ask for recommendations from your friends around town (or even on that handy facebook thing) and know that you may have to spend $100-300+ but it’s totally worth it.

all photos shown here are the raw photos taken by Photos By Kim around downtown portland, oregon and i’d highly recommend her for capturing professional but YOU images. we also hired her to do our new couples photos, which i’m really in love with and wrote a post on how to make those cute and not awkward. it’s also important to find a photographer you feel comfortable with and who can have fun!

find the balance of using make-up

the only make up i wear regularly is mascara and eyeliner (you can watch my vlog about more beauty stuffy here). when i found out a make-up artist was actually included in the price of working with kim, i got a little nervous. i know most people would be thrilled but i was afraid that i might look like a clown since i never wear make up.

after meeting my make-up artist, i explained that i wanted my natural look to come through and not be a clown. she understood. she explained that by putting on some base foundation and make-up, it actually helps the photographer take better photos and do less edits on your skin including acne, oil and shine (even my husband got his nose powered).

how to take good headshots 1

the make-up artist also told me to quit plucking my eyebrows in the shape of a sperm. this caused me to laugh for 3 minutes straight but you know what i’m talking about, where there is more of a ball shape at the base and then gets skinny? don’t do that. if you’re experiencing that now, let them grown out.

throughout the shoot, she was there to touch up when needed and showed me a new trick with coconut oil! she carried a little jar of it in her purse, would ask me to bite my lips to get some more color in them and then would apply the coconut oil. this helped to keep my natural look too! she also somewhat joking told me how pissed she was that i had so much natural color in my lip and coconut oil was just to give it a gloss. i never knew this was something others might want so adding it to my ‘got it from my mama’ list!

show your (photographable) personality

just because you see everyone in blazers with a pop of color doesn’t mean that has to be your style (trust me, i tried it because i kept seeing it everywhere and well…nope).

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right before we were leaving our apartment with the photographer, i quickly ran to my closet and pulled out a polka dot green dress. i said that i knew you were only supposed to wear solids for professional photos, but i reeeeally like the dress. kim said “if you love it, then wear it! that should be a fun one to photograph!” remember, hire someone you like!

it’s true that you want to stick with more solid colors so it doesn’t distract from your beautiful face, but why not grab a fun pattern for a shot or two to have as options. we even got one with a donut!

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i’m not sure where i’ll use this yet but the fact that i have it makes me happy. and hungry.

be creative with the background

i’m a nature lady and kim found the perfect spot for what is now my favorite headshot. it has an awesome mossy tree in it as well as some brick. i’m wearing something simple but bold enough to show who i am. my father-in-law says i look like a hip doctor. maybe i need to go back to school and become dr. chelsea.

how to take good headshots 1

if you like the look of a studio shoot with a black, white, or gray background that’s awesome! if you don’t, there’s a whole world waiting to be your background. find scenes that fit your personality but still work for a professional shot.

have fun!

i know, it sounds a little cliche but i’m telling you, if you don’t have fun when you are taking your headshots, it will be noticeable. your authenticity shines through in photos in your eyes and in your smile. think of happy times, imagine the new job you’re going to get with these awesome headshots or recall something funny and unexpected that happened in your life (like when you let your husband get his travel vaccinations first and all hell broke loose).

how to take good headshots 1

be authentic

this relates directly to having fun. the camera can tell when you aren’t being authentic and as i said in the couple’s shoot post, it’s all in the eyes and the mouth.

i shall use my husband as an example:

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he’s still super cute in this one but look at this smile and his eyes. now let’s compare it to the bottom one.

below he is genuinely laughing at something hilarious i said, i’m sure. you can see his eyes are slightly more squinted and he has a more authentic smile happening. this may too jovial for all of your headshot uses but for him, as a motivational speaker, it’s perfect! it shows that he’s full of energy, fun and would motivate your audience towards action.

how to take good headshots 1

so there you have it, how to take good headshots that aren’t so stuffy! of course, if you like the stuffy look, embrace and go with it but if it doesn’t feel like you…know that there is a whole world of uniqueness to capture who you are!

did i really make a pinnable graphic filled with my own face? i sure did. that’s how dedicated i am to proving there are ways to have a professional headshot filled with personality!

how to take fun headshots

what are you feelings on headshots? love them, hate them, find them curious?


  1. Drew

    November 4, 2015 at 8:46 am

    Your headshots look great! Does not diminish what you’re all about.
    Quite professional looking.
    Drew recently posted…Gentleness – Strength under Control

    • chelsea

      November 5, 2015 at 9:55 am

      thanks drew! i am quite happy with how they came out!

  2. Lisa @ Lisa the Vegetarian

    November 4, 2015 at 9:42 am

    Great tips! i feel like I should take a few headshots of myself for various networks such as Linked In, but I haven’t gotten around to it yet.
    Lisa @ Lisa the Vegetarian recently posted…Workout Week in Review: 10/26 – 11/1

    • chelsea

      November 5, 2015 at 9:56 am

      i feel you lisa, it’s easy to keep putting it off because it often doesn’t feel like a necessity but i can tell you – it’s exciting once they are done!

  3. Kate

    November 4, 2015 at 9:45 am

    Great point that you should make sure you’re being yourself! That really does come through in photos, and even if it’s just a classic blazer pose in a studio, it’s important that you’re comfortable. I’m always surprised by the number of cropped selfie looking photos I see on LinkedIn–nobody is going to take you seriously if you’re using a picture you took at some bar in college five years ago.
    Kate recently posted…Gettin’ Weird with Millicent: Basic Doods

    • chelsea

      November 5, 2015 at 9:57 am

      totally agreed that you’ve got to be comfortable in what you’re wearing, where you’re at and in who you are! seriously…some of those photos on linkedin are craaaazy (i was once guilty of this as well)

  4. chelsea jacobs

    November 4, 2015 at 10:08 am

    Yours turned out so good!
    chelsea jacobs recently posted…It’s Different, But it’s Good.

    • chelsea

      November 5, 2015 at 9:57 am

      thanks chelsea! i think she did a great job capturing who i am!

  5. Jennifer Haston

    November 4, 2015 at 12:49 pm

    I love headshots! Now that I have found the right photographer, you are right it makes such a difference. I had “good pictures” before but this most recent batch contains one that is so completely me… I was speechless and that is saying something! The funny thing is that as an actor I had headshots done for years but it wasn’t until I took headshots for speaking that I really found that “sweet spot” for my photos!

    You look great by the way, the black dress with you with your hand on your hip on top of “Authentic” is truly that.. Confidently you and you are so open and friendly..

    • chelsea

      November 5, 2015 at 9:59 am

      i am so glad you found the right photographer, jennifer and you are in love with your new shots YAY! funny how it all came together when you took your speaking headshots in additional the actor ones!

      thanks for your sweet words on photo, that is one of my favorites where i feel like it does capture many elements of me so thank you for confirming this 🙂

  6. Elyse

    November 4, 2015 at 2:45 pm

    Love your headshots!

    I did my first headshots as a kid and it was a VERY different experience than my work head shots. They were a bit stuffy but I suppose that’s what they were going with in my line of business…and it’s not like I had much of a say in them since it isn’t my company.
    Elyse recently posted…Feels Like Home Favourites – Toronto Restaurants

    • chelsea

      November 5, 2015 at 10:01 am

      oh man, headshots as a kid?! i am sure that is totally different than work headshots 🙂 yeah i’m sure it would be completely different if your company is taking them because they would want a uniform look for their website and what not. i bet you still looked awesome!

  7. Charlene

    November 5, 2015 at 7:56 am

    These are such great tips! I want to hire someone right now!
    Charlene recently posted…Thankful Thursday: Close Friends

    • chelsea

      November 5, 2015 at 10:02 am

      thanks so much charlene! it was a fun experience and now i don’t panic when someone asks for a photo 🙂

  8. Amanda

    November 8, 2015 at 5:15 pm

    Your shots are SO good! I need to take some fun, authentic ones again soon.
    Amanda recently posted…The FINAL Tell Me About Your Town Inspiration

    • chelsea

      November 9, 2015 at 9:30 am

      you have really great ones too amanda!!

  9. Jenn

    November 10, 2015 at 12:18 pm

    These are some great tips on getting a good headshot! I think one of my favorite suggestions for getting that staged smile to look a little more genuine, was to tell them to give a half-laugh. Like a “heh” to get them to quickly flare their nostrils and crack their smile just a tiny bit more. I think a smile where your top teeth don’t touch your bottom lip is very photogenic, and I see that in the second photo of your husband. With a little squint to the eyes and tipping the chin up, ever so slightly, you also look confident and relaxed.