Three Tips to Slay Your Headshots


Recently a good friend asked me what to wear for her headshots and I immediately empathized. It's the age-old question every professional woman faces at least once in her career and no matter how far in advance you pick out your outfit, chances are you'll end up emptying your closet unto your bed in search of the "perfect" dress. Oh, that's just me?

As someone who’s had three (yes, three!) headshot photo shoots in less than two years, I'm more than happy to share some insight. But first, let me share some examples of what NOT to do...

Exhibit A


No, no, no. Everything about this is all wrong. Can you tell I read every Pinterest post about what to wear to a headshot and attempted to cram it all into one shot? Cliche Chicago mural? Check. Blouse and blazer? Check. Statement necklace? Check. And as for my hair and makeup? It's TEW MUCH! Too dramatic, too poofy ... too everything. I was doing the most with the very least, for reals.

About a month or so later, I took new headshots ...

Exhibit B


For this round, I did my own makeup and visited my natural habitat ... a cupcake shop. I brought props, such as my laptop, journal, books and magazines and instantly felt more comfortable. And look at all of the colors! Even though I used this headshot for everything, something still felt a bit off. I don't typically wear my hair like this, so it didn't really feel like me.

But third time is a charm!

Exhibit C


For this look, I had my hair and makeup professionally done by women I know and trust and I'd saved up to shoot with Chuck Olu-Alabi, a Chicago-based photographer whom I'd admired for years. What can I say? Third time is a charm!

Read on to learn more about my tips and tricks to slay your headshots:

To thine own self be true.

You saw what happened when I tried to emulate all of the popular Pinterest posts instead of sticking to my typical work uniform. I feel most comfortable and confident in a dress, not a blazer (the fact that I bought one specifically for this purpose should have been a dead giveaway). Wear something you'd normally wear to work or to a job interview. You can never go wrong with business-casual. I repeat, do NOT try the trendy blouse/blazer combo unless this is something you'd actually wear IRL. When in doubt, ask a trusted friend for their input.


Choose hair and makeup people you trust.

This is not the time to try out someone new or simply book a random off of Groupon. It helps that I've been going to my hairstylist (Lalitha Arnold) for years and my makeup artist (Capri Latimore) is her assistant, so they know what I look like on an everyday basis. My advice here is similar to when you're considering what to wear: aim for a more polished version of yourself. In my case, this consisted of a blowout and natural/soft makeup with a nude lip. Voila.


Invest in a professional photographer.

As I mentioned earlier, I'd been admiring Chuck's work for a few years and for good reason. He's photographed some of my favorite Chicago bloggers, including Luvvie and Afrobella. For me to get to their level, I knew I had to save up some coins. It took me a little while, but the investment was well worth it. I immediately felt a connection with Chuck and laughed throughout most of the shoot, which (fun fact) makes for great photos.I started a secret Pinterest board full of outfits, locations and poses that I liked and showed them to Chuck before the shoot. I explained to him that I wanted an "urban chic" look in my pictures and he instantly understand the vibe I was going for. Nailed it!

At the end of the day, you want to look like you, just better. No more, no less. There's a ton of advice out there about avoiding prints, bright colors, etc. and to that I say, pshaw! Wear what makes you feel good and look good. Laugh like there's no tomorrow. And shoot with someone you feel comfortable with ... the chemistry will come through in the photos.

And don't worry about the poses. Any photographer worth their salt will make sure you're working it, honey! And remember, Photoshop is your friend. Not saying you're going to come out of this looking like Beyoncé, but the goal is to look like your best self.

Do you have a question you'd like me to answer? Drop a line at!