I hear this one all the time: “My headshot’s only three years old. It still looks like me.”

And technically? Sure. You haven’t changed species. Your eye color’s the same. But here’s what most people don’t realize until it’s too late — outdated headshots create a disconnect before you ever shake someone’s hand.

Think about the last time you met someone in person after seeing their photo online. If there was even a slight “wait, is that them?” moment, you felt it. That split-second hesitation isn’t about vanity. It’s about trust.

Outdated headshots aren’t just photos that are “old.” They’re professional images that no longer accurately reflect how you look, how you carry yourself, or the role you play today — even if they were taken only a few years ago.

“My Headshot Is Still Fine” — A Common Belief

Let’s be honest about why professionals put off getting new headshots:

They like how they looked. Maybe it was a good hair day. Maybe they were 15 pounds lighter. Maybe they just felt confident that day, and the photo captured it. There’s an emotional attachment there.

It feels expensive for “just a photo.” When you’re weighing business expenses, a headshot session can seem like a luxury compared to, say, new software or marketing tools.

They don’t think it matters that much. “People care about my work, not my face.” Except your face is often the first thing people see before they ever consider your work.

Change is incremental. You see yourself every day. The grey hair, the new glasses, the slight shift in how you carry yourself — it all happens so gradually that you don’t notice. But everyone else does.

What Changes Faster Than You Think

Here’s what I’ve learned shooting corporate headshot photography for decades: The things that make you look dated aren’t always obvious.

Your Role Has Evolved

That headshot from when you were a junior associate? It might still look like you, but it doesn’t look like the senior director you’ve become. There’s a different energy in how someone carries themselves at different career stages. Confidence looks different. Authority looks different.

I photographed a client who’d been promoted twice since her last headshot. She walked in wearing the same blazer, but everything else had changed — her posture, how she made eye contact, even how she smiled. The old photo wasn’t wrong, but it wasn’t telling the right story anymore.

Confidence Shifts

Maybe you’ve been through something — launched your own business, survived a difficult year, became a parent, hit a major milestone. Those experiences change how you show up. And that should be reflected in your professional branding photos.

Your headshot should match the version of you that walks into the room, not the version from three career moves ago.

Industry Expectations Move Quickly

Remember when everyone wore suits in their headshots? Now half my corporate clients show up in smart casual and want something less rigid. Styles change. Norms shift. What looked current in 2020 can look surprisingly dated in 2025.

Even things like lighting trends and background choices evolve. That soft-focus, heavily retouched look from a few years ago? It reads as trying too hard now. People want authenticity.

Your Personal Brand Has Developed

Maybe you’ve narrowed your niche. Maybe you’ve expanded your services. Maybe you’ve repositioned yourself in the market entirely. Your visual representation should evolve with that.

I work with a lot of executives transitioning into consulting or board work. The “corporate employee” headshot doesn’t serve them anymore. They need something that says “trusted advisor” instead.

The Trust Gap Old Photos Create

Here’s the thing about outdated headshots — they don’t fail spectacularly. They fail quietly, in ways you never hear about.

Looking Different in Real Life vs. Online

Someone finds you on LinkedIn. Your photo shows you with dark hair, clean-shaven, maybe wearing glasses. They walk into your office six months later, and you’ve got grey hair now, grew a beard, switched to contacts.

It’s not catfishing. It’s just… off. And that “off” feeling plants a tiny seed of doubt before the conversation even starts.

Subtle Credibility Erosion

This is the insidious part. People won’t tell you your headshot looks old. They’ll just… not reach out. Or they’ll pick someone else whose entire online presence feels current and dialed in.

Research on first impressions consistently shows that people form judgments within seconds, and visual cues dominate early trust decisions. Your headshot does more work upfront than your resume ever will.

Your headshot is part of a larger ecosystem — your website, your LinkedIn profile photo, your email signature, your speaker bio. When the photo feels dated, it makes everything else feel dated too. Even if your credentials are impeccable.

If you’re reading this and mentally justifying why your current headshot is “probably fine,” that hesitation alone is usually the answer.

Think about it: If someone’s website has a 2015-era design, you question whether their approach is current. Same principle applies to headshots. Good branding eliminates confusion. An old photo introduces variables you don’t want people thinking about.

Why High-Level Professionals Update More Often

I photograph a lot of CEOs, board members, senior partners. And here’s what I’ve noticed: The higher up someone is, the more frequently they update their headshot.

It’s not vanity. It’s strategic.

Alignment, Not Vanity

When you’re representing a company, a practice, a brand — your image is part of the messaging. Keeping it current isn’t about looking younger or better. It’s about alignment.

If your company just went through a rebrand, your old headshot with the dated styling might conflict with the new visual identity. If your firm is positioning itself as innovative and forward-thinking, but your leadership team’s headshots look like they were taken in 2012, there’s a disconnect.

Staying Current Visually

High-level professionals understand that their professional headshot is working 24/7. It’s on their website, in pitch decks, in press releases, at conferences, in award announcements.

One of my clients, a managing partner at a law firm, updates his headshot every 18 months like clockwork. Not because he’s vain, but because he knows his photo gets seen by prospective clients, recruits, and colleagues hundreds of times a year. It’s a business tool that needs maintenance, just like anything else.

Quick Self-Check: Is Your Headshot Outdated?

Ask yourself:

• Does this photo still look like me today?
• Would someone recognize me instantly if we met in person?
• Does this image match my current role or seniority?
• Does it align with how my industry presents itself now?
• Do I feel confident sending this photo to a high-stakes client?

If you hesitated on any of these, your headshot is already working against you.

How Often Should You Update a Professional Headshot?

There’s no one-size-fits-all answer, but here are some good guidelines:

Every 1-2 years as a baseline. Even if nothing major has changed, styles and expectations evolve enough that a two-year-old photo starts to look noticeably dated.

After a significant appearance change. New glasses, different hairstyle, weight change, facial hair — anything that makes the photo feel mismatched with how you look now.

When your role changes substantially. Promotion, new position, career pivot, launching your own business. These shifts warrant a visual update.

If your industry or brand evolves. Rebranding, repositioning, new company, new messaging — your headshot should align with where you’re going, not just where you’ve been.

When you feel disconnected from the photo. If you look at your current headshot and think “that doesn’t really feel like me anymore,” trust that instinct. Others are probably feeling it too.

I tell clients this: If you’re questioning whether it’s time to update professional headshot photos, it’s probably time.

Final Thought: Your Photo Should Match the Room You’re Walking Into

Here’s how I think about it: Your headshot should represent the version of you that walks into the room.

Not the version from three years ago. Not the version you hope to become someday. The version that shows up now — confident, current, credible.

Because here’s the reality: People form impressions fast. Before they read your bio, before they review your credentials, before they hear you speak — they see your photo. And that photo is either building trust or introducing doubt.

Outdated headshots don’t just look old. They make you look out of touch, even when you’re not. They create friction where there should be flow.

So if you’re still using that headshot from 2020, or 2018, or — let’s be honest — 2015? It might be worth asking yourself: Does this photo still represent who I am today?

If the answer is anything other than an immediate yes, it’s time.

👉 Ready for a headshot that actually matches the professional you are today? Let’s create something current, confident, and authentically you. Schedule a session with Alex Kaplan Photography in Northern New Jersey or the NYC metro area.