2025 Headshot Trends: What High-Level Clients Look For (and What’s Outdated)
In a world where everyone is Googling and ChatGPT'ing everyone, your headshot is your first impression, and it’s happening before you even say a word.
Especially here in the San Francisco Bay Area, where first impressions happen on LinkedIn, Zoom, team pages, and pitch decks, your photo is doing the talking long before you walk into the room.
For high-level professionals in tech, design, venture capital, law, and leadership roles, your headshot isn’t just a box to check. It’s a strategic tool in your personal brand. And when done well, it becomes a visual flex: current, confident, and clearly communicating who you are.
Let’s talk about what works in 2025, what doesn’t, and why your next headshot should look like it belongs in this decade.
1. Outdated headshots are the new "business casual" (aka, maybe not the compliment you think it is)
That headshot you took 8 years ago? It’s not timeless…it’s…just old. In 2025, clients and colleagues are looking for signs that you’re current, aware, and investing in your professional image. If your headshot still looks like it was taken at a mall photo studio or during your company’s 2016 offsite, it’s likely working against you.
High-performing clients know that perception matters, especially in industries like tech and professional services where visual communication is constant. A modern image signals that you get it.
2. Personality is in. Bland is out.
Generic smiles, stiff poses, and plain backgrounds scream "forgettable." The best headshots in 2025 feel elevated and authentic. Think: relaxed expressions, confident energy, premium lighting, subtle color tones, and editorial polish.
Especially in creative, tech, and consulting roles, clients want to work with real people with real personalities and emotions. Not an Ai representation. You don’t need to wear a hoodie to signal innovation (i joke, i joke), but you do need to look like someone who has warmth, presence and personality.
3. Boutique Retouching > One-Size-Fits-All Filters
We’re deep in the AI age—and that means people can spot AI-generated or over-edited images from a mile away. Instead of soft blurs or face-smoothing apps, high-end professionals are opting for bespoke, boutique-level retouching that feels intentional and invisible.
San Francisco and Silicon Valley professionals want to look polished, powerful, and real. That means hiring photographers who understand nuance and how to highlight natural features while maintaining depth, clarity and personality.
4. You Are Your Brand (So Let’s Show That)
Whether you’re pitching to VCs, leading teams, building your consultancy, or gunning for a board seat, your headshot needs to support the brand you’ve worked hard to build. That might mean wearing color. That might mean keeping it classic. A new haridoo? I dunno, but it should feel like you.
A great photographer helps you dial in your visual identity so that it aligns with where you’re going, not just where you’ve been.
5. One Headshot Isn’t Enough Anymore
In 2025, leaders are showing up in more spaces than ever: podcast guest spots, conference bios, Substack newsletters, Forbes articles, Zoom panels, startup websites, investor decks. Each platform needs its own flavor of visual. Multiple images with a range of personality, vibe and style can go a long way. Different images for different platforms and use cases.
6. Your Next Client, Job, or Opportunity Will Probably See Your Face First
Let’s keep it real. In the Bay Area business scene—especially in San Francisco and Silicon Valley—your photo is often the first thing decision-makers see. Before your resume, before your credentials, before the email gets read.
What does your current headshot say about you? Are you gonna stop the scroll? Are they going to remember you? Are you giving intention, taste, confidence, leadership? If not—it’s time..
7. Your Visual Identity Still Matters in the Age of AI
In 2025, artificial intelligence is writing blogs, building websites, and even generating profile pictures. But while automation has exploded, it’s made authenticity more valuable than ever.
When clients, investors, or hiring managers are vetting people, they’re not just looking at your resume—they’re scanning for signs that you’re real, current, and aligned with your personal brand. That means your headshot isn’t just for show.
Real people still want to work with real people. And even the most advanced systems (think, search engine, smart recommendations or most likely a new Ai algorythm) are looking for clear, consistent signals of credibility, and it starts with a great, real, honest image of YOU.
A modern, professional image helps you show up strong, both for the humans and the tech. Hire the right person (ME) and I will help get you through this.
Book a Headshot That Works as Hard as You Do
If you’re ready for a photo that elevates your presence and actually feels like you, I’d love to work together. I specialize in professional headshots, brand photography, and creative portraits that help high-level clients across San Francisco and beyond look like the mf boss that they are.
We're on the same team. Hit me up! brian@briandesimone.com
Brian DeSimone
Oakland photographer making executives, founders, and creatives look expensive and interesting. Available throughout the Bay Area for editorial, brand, and corporate work.
