What's the most common headshot mistake?

Wearing the wrong wardrobe. Specifically: busy patterns, logos, and ill-fitting clothing. Wardrobe issues show up more than any other single variable in final images, and they're almost always avoidable with some pre-session thought.

Is a smiling or serious headshot better?

Neither is universally better — it depends on your industry, personal brand, and how the image will be used. Most sessions include both. The mistake is forcing an expression that doesn't feel natural, which reads as awkwardness regardless of whether you're smiling or serious.

Can I do my own headshot with an iPhone?

Modern phones take competent casual photos, but a self-shot image usually can't replicate professional lighting, posing guidance, and editing. The gap is widest at the very use cases where headshots matter most — LinkedIn, casting, executive profiles.

Should I get headshots retaken if I don't like them?

Depends on why you don't like them. If the technical execution is poor (lighting, sharpness, posing), reshoot. If it's that you don't like how you look generally, a reshoot probably won't solve that — and a conversation with the photographer about the editing approach might.

How do I avoid looking stiff in my headshot?

The most reliable trick is getting comfortable with the photographer before the shooting starts. Spend the first few minutes talking. Stiffness almost always comes from tension, and tension dissolves when the session feels like a conversation rather than a performance.

Headshot Mistakes to Avoid (Seen by a Boston Photographer)

The most common headshot mistakes that hurt final images — from a Boston photographer who has shot thousands of sessions. What to avoid and why, for Boston and South Shore clients.

After thousands of headshot sessions in the Boston area, patterns emerge. The same mistakes show up repeatedly, and they're almost all avoidable with a little pre-session awareness. Here's an honest catalog of what goes wrong most often — and what to do about it.

Wardrobe Mistakes

The single biggest category. Wardrobe issues show up in more headshots than any other variable.

Busy patterns. Small-scale patterns (fine stripes, houndstooth, detailed checks) create visual noise and can even produce moiré effects — a wavy distortion where the pattern interacts badly with the camera sensor. Solid colors or very subtle patterns photograph cleanly.

Logos and text. Logos and graphic text on clothing pull the viewer's eye away from the face. In headshots, you want the face to be the focal point. Any visible text or prominent logo undermines that.

Poor fit. Shirts that bunch at the shoulders. Jackets that pull across the chest. Collars that gap. These issues look minor in person but become obvious on camera, especially in mid-body or waist-up framing. Well-fitted pieces — even inexpensive ones — photograph better than expensive pieces that don't fit properly.

Too trendy. Headshots last 2–3 years, sometimes longer. Anything that will look dated in 18 months becomes a problem. Very specific trends, unusual colors, and of-the-moment silhouettes can all age quickly.

All black (for men, especially). A full black shirt with a black jacket on a dark background can make the subject look like a floating head. This isn't universal — it can work with the right lighting — but most of the time, some tonal variation between wardrobe and background serves the image better.

See the headshot wardrobe guide for specifics.

Posing Mistakes

Most of these aren't your mistakes — they're a photographer's failure to guide. But some are worth naming so you know what to push back on if you see them happening.

Square-on shoulders. Shoulders directly facing the camera flatten the body and create a blocky silhouette. A slight turn (15–30 degrees off-axis) adds dimension and produces a more natural-looking image.

Chin up or chin down extremes. Chin too high looks arrogant. Chin too low creates double-chin issues and makes the eyes look small. There's a narrow band of chin position that works, and a good photographer dials it in for you.

Forced smile. A held smile that was cued on "3-2-1" almost always reads stiff. Real smile energy comes from the moment between cues — a joke that actually landed, a mid-conversation exchange. The photographer's job is to create those moments; your job is to let them happen.

Hands awkwardness in waist-up shots. Most people don't know what to do with their hands. Options: arms crossed (reads confident but can seem closed), hands in pockets (casual, works for some industries), arm on hip, or one hand in pocket / one at side. The mistake is hands dangling awkwardly — not any specific position.

Expression Mistakes

Defaulting to one expression because you're self-conscious about another. Many clients avoid smiling because they dislike their teeth, or avoid serious expressions because they think they look angry. The result is a narrow range of images that don't represent you fully. A good session produces both, and you pick.

Freezing. Locking into a held expression instead of cycling through micro-expressions. The photographer should be talking, cueing, and keeping the face active throughout the shoot. If you find yourself holding still, say so — we'll reset.

Not trusting the preview. Clients sometimes hate an image in the preview and then love it in the final gallery after editing and selection. The camera back is a small, harshly-lit LCD; it's not how the final image will look. Trust the process.

Lighting Mistakes (On the Photographer's Side)

If you're working with an experienced photographer, these shouldn't be issues. But if you're shooting with a newer photographer or doing something DIY, watch for:

Flat front lighting. Light directly in front of the subject produces a flat, one-dimensional look with no shape or depth. Good headshot lighting comes from a slight angle.

Overhead lighting creating under-eye shadows. Raccoon eyes from a poorly positioned softbox are a common tell of amateur lighting setups.

Background spill. Light bleeding onto the background from the subject lighting creates hot spots and unflattering gradients. Background lighting should be controlled separately.

Preparation Mistakes

Booking the session without sleeping the night before. Tiredness shows up around the eyes and in skin tone. If you can, don't schedule the session after a brutal week — the images will reflect it.

Haircut timing. Too close to the session (same day, day before) and the cut hasn't settled. Too far out (3+ weeks) and it's growing unevenly. Sweet spot: 4–7 days before the session.

Alcohol the night before. Even moderate drinking shows up as puffiness and dullness in skin. If the session matters, skip it.

Salty food the night before. Same issue — morning-of puffiness is real and visible in close-up portraits.

Dehydration. Dehydrated skin reads differently on camera. Drink water consistently for a few days before the session, not just the morning of.

Retouching Mistakes

Asking for over-retouching. Heavy retouching produces images that look plastic and disconnected from the actual appearance of the person. Over-retouched headshots are often less effective than moderately retouched ones because the mismatch between the image and reality undermines trust.

Asking for no retouching. The other extreme. Transient marks (waistband lines, fresh blemishes, temporary redness) that aren't part of your regular appearance should be reduced. An unedited image captures whatever happened to be on your skin that specific day, which isn't what you want representing you for the next two years.

Not flagging specific concerns. If you have a concern about a specific feature — a scar, a mark, a feature you feel self-conscious about — flag it during the consultation. A good photographer adjusts posing and editing to address the concern.

Platform Mistakes

Using the same image for every context. LinkedIn wants one thing; a speaker bio wants another; a casting site wants another. Modern sessions often produce 2–3 distinct looks to avoid forcing one image to cover every use case.

Outdated images. Headshots older than 3–4 years almost always need refreshing. See how often to update your headshot for more.

Low-resolution uploads. Some platforms compress heavily. If the original file is already small, compression makes it worse. Upload the highest resolution the platform allows.

Ready to Book?

Get in touch to schedule your session and we'll discuss preparation during the consultation. Photography Shark is based in Rockland, MA, serving Boston and the full South Shore.