The Modern Headshot

Style Guide

At Flytographer, The Modern Headshot is about YOU — your brand, your personality, your style. It’s about showing the world who you are. Gone are the days of cheesy or stiff portraits that say nothing about the person in the photo. The tried-and-true tenet of people doing business with those they like and trust starts with your personal brand identity, whether you are a professional, a student, an entrepreneur or a creative. Booking with Flytographer is the first step in the right direction! Read on for some tips for what to wear and how to prepare for your own Modern Headshot.



First things first — before you decide on clothing, you need to decide on how you want to portray yourself and your brand. Write down some keywords that speak to your brand (fun, traditional, hip, approachable, trustworthy, serious, etc) and stick to that as you start building out your headshot plan. Then spend a bit of time looking at headshots and portraits of others in your industry. How are they conveying their message through their photos? Are they successful? Why or why not? Every industry has a different social code, so an actor’s headshot will look different than a lawyer’s headshot, which in turn will look different than a web developer or graphic designer, and so on. What would you do differently or the same as others you’ve seen? Use your answers to these questions to help guide you to getting what you want from your shoot.

Another trick to get really precise with your look is to imagine yourself in a scenario such as meeting an important client or being interviewed for your dream job or headlining at an industry conference — what would you wear and how would you present yourself with hair/makeup? If it’s not appropriate for this scenario, it’s probably not appropriate for your headshot. Your style should match to that of your audience.


1. Fit is key. Wear something that fits you really well, neither too tight nor too baggy. You’ve heard it before, and we’ll say it again: a tailor is your best friend. Try on your outfit and check yourself in a full-length mirror, turning around to see it from all angles. If an item you love is not the perfect fit, take it to be tailored. 

2. The daylight test. Take your outfit for a test run outside and ask a friend to snap a photo of you. Make sure that when you wear it in bright daylight, nothing is too transparent and that you are wearing the correct undergarments (no patterned bras under a white shirt!). Every little detail counts.

3. Avoid trends. It’s best to choose something modern yet classic that won’t put a timestamp on you in six months. You can’t go wrong with a classic button-down shirt, a v-neck pullover, suit jacket, or similar style that speaks to your industry.  

4. Colours, patterns, and logos, oh my! Although many people love to wear black, it tends to be a clothing colour that can be hard to photograph as it can fall flat in pictures. Consider elegant alternatives like navy, grey or eggplant. A colour that closely resembles your skin tone should also be avoided, as you won’t get those contrasting lines between you and your clothing. Bright, loud colours are another no-go as they will pull focus away from you, as will distracting patterns. You want people to first see you when they look at the photo, not your clothes. Avoid logos too unless they somehow tell the story of your brand, such as your own logo, or a fashion blogger repping a particular brand.

5. Jewellery. The same can be said for jewellery — a little goes a long way. Wear what represents you but don’t go overboard and distract people with too much or too big. As Coco Chanel once wisely advised, “Before you leave the house, look in the mirror and take one thing off.” It’s you that needs to shine, not your bling.

6. Comfort is king. If you feel uncomfortable in it, that feeling will translate to your photos. Wear something that not only look goods but also feels good. Make sure you can move in it and there isn’t anything restricting.  

7. Think about your feet. Shoes say a lot about who you are, so be intentional when you choose a pair for your shoot. Make sure they are polished and clean. Pro tip: Bring one pair of comfy walking shoes for moving between locations and keep your “photo shoot shoes” neat and clean in a bag, worn only when you have arrived at your shoot location or when you will be doing full-body shots. 

8. Layer up! Layers are a fantastic way to easily diversify your look. Think about jackets, scarves, or sweaters layered over your shirt or dress, and then remove them to capture different looks without having to change your core outfit. 

9. A word about glasses. Reflective glare in photos is a common frustration for eyeglass wearers. You can choose not to wear glasses for your shoot to eliminate this issue, but if your specs are part of your daily look, you probably want to have them in your headshot. If you don’t have anti-reflective lenses, you could visit your optometrist to either have them put in or see if they can temporarily remove your lenses altogether for the shoot … or instead perhaps they can lend you a pair of glassless frames for the day. Pro tip: if you do wear glasses but are removing them for the shoot, try to keep them off for a least an hour beforehand so you don’t have those little red marks pressed into the side of your nose.

10. Wear a smile. Nothing looks better on you than a genuine smile and authentic confidence. If you feel good, you look good, so own it during your shoot. The best tip for this is to practice in front of a mirror. It may feel silly, but practicing some poses and smiles, tilts of your head, body angles, etc will set you up for success. You know better than anyone how you want to look. If you’ve practiced your moves so they feel second nature, it will make your shoot go much more smoothly as you’ll just flow into them. Pro tip: think about one thing that always brings a real smile to your face and type it into your phone. Right before your shoot, read what you’ve written and then keep those words top of mind when you get in front of the camera to produce the real smiles you are after.


  • Cut and colour early. Get your hair cut and/or coloured 3-7 days before your shoot to give your hair the time it needs to “settle in.” 
  • Makeup should be fresh and natural (unless you are going for a glam look!); you don’t need much more makeup than you would normally wear. (For video or film, actors wear a lot of makeup, but for still photos, you don’t need nearly as much.) Avoid anything sparkly!
  • The emphasis will be on your eyes and mouth, so pay particular attention to these features. Make sure mascara is applied evenly and eyeliner isn’t running or smudged, and that your lips are always hydrated. Bring chapstick and extra lipstick to apply as you go.
  • Wear matte foundation and bring a blotter or translucent powder to eliminate any shine while on the shoot.


While you don’t want to have lots of things to pack around with you, it’s always a good idea to come prepared with your personal “style kit” in case of emergencies. 

Some ideas of things to bring:

  • Your shoes (see tip above)
  • Small bottle of lotion for chapped hands or feet
  • Chapstick to keep lips hydrated
  • Lipstick (if wearing) for touch-ups
  • Pack of wet wipes for unexpected scuff marks or dirt
  • Stain remover pen
  • Travel pack of tissues
  • Hand mirror to check teeth, makeup
  • Hair brush
  • Hair spray
  • Clothes pins (to clip or hold anything on your outfit that might need it)
  • Lint roller/brush
  • Small pair of nail scissors (for loose threads etc)
  • Extra nylons/stockings if wearing them
  • Bottle of water

The secret to having a successful personal branding shoot is in really knowing who you are and what your brand is all about, and also knowing where you will be using your photos so you can speak to your targeted audience. Are the photos for your website, your resume, your founder’s profile, your dating app? Once you are set in that knowledge, you can be really intentional in making all the right decisions to get you to your shoot day. And in the end, The Modern Headshot shoot is really fun! It’s an opportunity to work with a pro photographer who is going to help you translate your vision to connect with your audience. We know a great headshot is just the start of bigger things for you!

Have a great shoot!

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