Most Common Headshot Mistakes I See (And How to Avoid Them)
Your headshot is easily one of the most hardworking pieces of your personal brand. It’s out there 24/7 representing you on LinkedIn, your company site, and even in that little thumbnail in your email signature. It needs to look professional, sure… but more importantly, it needs to look like you.
Over the years, I’ve photographed hundreds of professionals here in my Westport studio. I’ve seen it all: people rushing in straight from a stressful commute, wearing shirts with the store creases still visible, or just flat-out overthinking every single hair. The good news? Most headshot "fails" are actually really easy to avoid.
Here’s the breakdown of what I see most often, and how we can make sure your session is actually a win.
1. Picking the "Great in Person, Bad on Camera" Outfit
The biggest wardrobe mistake isn't wearing something "ugly" - it's wearing something that just doesn't photograph well. Busy patterns, neon colors, and super-shiny fabrics tend to "vibrate" on digital screens and pull all the attention away from your face. On the flip side, clothes that are too baggy or dark can swallow you up and zap your energy.
The Fix: Stick to solid colors. Navy, charcoal, soft blues, and even jewel tones look good on almost everyone. I provide a PDF guide for my clients on wardrobe before they even show up. And we’ll also look through your options together, selecting what will photograph well with the lights and the background (not to mention your skin-tone and hair color). You don’t need a new wardrobe; you just need three or four pieces that make you feel like a boss.
2. Skipping the "Tiny" Grooming Details
It’s easy to overlook a messy collar or some visible lint when you're in a rush, but the camera is a perfectionist.
The Fix: A little prep goes a long way. If you’re getting a haircut, do it about a week before your session so it looks natural, not "fresh out of the chair." For the guys, a quick trim of facial hair or eyebrows makes a huge difference in definition. For the ladies, keep makeup clean and natural so it stays timeless. I always have styling tools and a mirror ready at the studio for those last-minute "did I miss a spot?" checks and I’m constantly keeping an eye on all the details as well!
3. The "I’m Not Photogenic" Mental Loop
Almost everyone walks into my studio and says, “I’m so awkward in photos.” Not being photogenic is a real thing, but it has more to do with how relaxed you are in front of the camera than some actual failing on your part.. in other words, it’s 100% fixable!
The Fix: Don’t worry about trying to find a "perfect" pose. That’s my job. I’ll guide you through every shift of your chin and shoulders. We can even look at the images on screen as we go, so you can see exactly what’s working in real time. Once you see that you actually can look relaxed, the nerves usually just evaporate.
4. Settling for "One-Size-Fits-All" Lighting
Bad lighting is the fastest way to exaggerate shadows or get a weird skin tone. This is why professional headshot photographers spend years obsessed with light (not to mention spend a lot of money on lighting gear). After many years, I still haven’t found the one lighting setup that works for everyone - I always have to adjust lights for the person I’m photographing because everyone is so different!
The Fix: In my studio, I don’t use a "static" setup. I customize the lights for you - your bone structure, your skin tone, and even what you’re wearing. Whether you want a high-power corporate look or a softer, creative vibe, the lighting should do the heavy lifting so you actually look good in your photo.
5. Clashing with Your Background
A busy outdoor background or a backdrop color that fights with your outfit is a major distraction. The background shouldn't be the star of the show; it should be the frame that makes you stand out.
The Fix: We’ll pick a backdrop based on your goals. Neutral tones (white/gray) are the gold standard for corporate work, while darker, moodier setups can add a bit of drama for creative fields. If I’m shooting a whole team, I make sure the backgrounds stay consistent so the company page looks like a unified front, even if we shoot over different days (or years!).
6. Hiring a "Generalist" Photographer
A common mistake is assuming anyone with a nice camera can take a headshot. But headshots are a very specific niche - it’s really about human expression and micro-movements more-so than the camera setup.
The Fix: Work with a specialist. My process is built around making sure you don’t feel rushed or unsure. You’re not just paying for a high-res file; you’re paying for the direction that gets you to look approachable and confident at the same time.
7. Falling into the "Airbrushed" Trap
Over-editing is a huge mistake. If your skin looks like plastic or your eyes are glowing like a sci-fi character, people will feel a disconnect when they meet you in person.
The Fix: Retouching should be "polishing," not "rewriting." I’ll handle stray hairs, lint, or a temporary blemish, but I’m leaving your natural skin texture intact. You should look like yourself on your absolute best hair day - period. But the key here really is to look like yourself!
8. Holding Onto a "Vintage" Version of Yourself
If your headshot is five years old (or from three jobs ago), it’s sending the wrong message. If your hair or style has changed significantly, your photo needs to catch up. I know we all looked young and beautiful five years ago!
The Fix: I recommend an update every two to three years. It keeps your brand fresh and shows you’re active. For companies, I will often do an on-site to refresh for the whole team at once, ensuring everyone from the CEO to the newest hire looks like they belong to the same era, with rolling updates for team members about two years after that.
9. Rushing the Selection Process
A lot of people just pick the first photo they don’t hate because they’re tired of looking at themselves - or get overwhelmed with how to make the best selection. That’s a missed opportunity.
The Fix: We take our time. After your photo session, we’ll sit down and review your images in person, together. We’ll talk about which expression communicates "confidence" versus "approachability" and which pose works best for your body type. I help you decide and I walk you through the specific methodology of my process. You’ll leave the Studio having made the best selection and knowing exactly what you’re getting in the end.
10. Treating it Like a Chore
If you show up thinking of this as a "task" to check off, that tension is going to show up in your jaw and your eyes.
The Fix: Think of this as an investment in your career. When you show up with an open mind and the willingness to work together, the session actually becomes fun. I try to handle everything for you, as much as I can - from wardrobe tips to a 48-hour turnaround on your final retouched shots.
The best headshots aren’t about perfection. They’re about authenticity, confidence, and connection. Avoiding these common mistakes helps you walk away with an image that feels like you - and that’s what people respond to most.
A professional headshot tells the world you take your work seriously, that you’re approachable, and that you’re ready for new opportunities. If it’s been a few years since your last one, or if you’ve never had a truly professional experience, it might be time.
When you’re ready, I’ll make the process easy from start to finish. You’ll leave my Studio knowing exactly which image works best for you - and with a headshot that makes the right impression every time.
