San Diego Headshots Designed to Make Professionals and Teams Look Confident and Approachable
Every professional deserves a headshot that’s authentic, confident, and approachable. I create images that show your personality while keeping you polished and professional. Perfect for LinkedIn profiles, corporate websites, or team pages, your headshot will make a memorable first impression.
Headshot Photography That Feels Natural, Looks Professional, and Captures
the Real You
I make the headshot process simple and comfortable. With guidance on posing, expression, and style, you’ll feel at ease in front of the camera—and walk away with images that feel authentic, confident, and ready to move your career forward.
Professional Headshots Without the Stress
You’re not just booking a headshot.
You’re stepping into the next version of you.
Maybe you're building a brand, taking your career to the next level, or you're just tired of hiding behind that outdated photo. Whatever brought you here, you're ready to be seen. Really seen, in a way that feels authentically you: confident, approachable, and aligned with where you're going. Professional headshots are the foundation of making that powerful first impression.
I'm Cary, a San Diego headshot and branding photographer, and I help attorneys, business professionals, realtors and many others to show up powerfully and naturally in front of the camera. My sessions are relaxed and guided, tailored to who you are and what you're creating. No cheesy smiles or stiff poses. Just professional headshots that speak for you before you even say a word.
Whether you're in San Diego or Carlsbad, my branding photography sessions capture the authentic professional image that sets you apart in your industry. These aren't just photos – they're strategic headshots designed to elevate your personal brand and connect with your ideal clients.
You bring the vision.
I’ll help the world see it.
Headshot Experience
With over 20 years of experience helping people look their best while feeling relaxed and confident, I create images that truly reflect who you are — approachable, professional, and full of personality.
Professionalism
Committed to giving you more than just stunning professional headshots — we focus on clear communication and a seamless experience from start to finish.
Customer Service
Exceptional customer service is at the heart of every headshot session. From the first inquiry to final delivery, we’re here to make the process simple, supportive, and stress-free.
Trusted by People Just Like You
30+ Google Reviews That Speak for Themselves
30+ Yelp Reviews That Speak for Themselves
Working With the Best Clients and Partners
The Process
1
Booking Made Easy
Scheduling your session should be the easiest part—our simple online booking lets you choose a date and time that fits your lifestyle. Individual sessions can be booked up to 7 days in advance. Need something custom or have questions? I’m just a call or email away—happy to help however I can.
3
Confidence Looks Good on You
From start to finish, we guide you through natural, flattering poses that reflect your personality and professional vibe—so you’ll never feel stiff or unsure. With our instant image review process, you’ll leave your session knowing we’ve captured headshots you’re truly proud of.
2
Creating the look
Once you book your session, you’ll receive a quick and easy questionnaire to help me get to know your headshot goals. We’ll cover things like the vibe you’re going for, background preferences, wardrobe choices, and colors that flatter you—so we can create headshots that truly feel like you and look amazing.
4
A Headshot You’re Proud to Share
Our expert retouching highlights your natural features without ever feeling overdone—just a clean, confident version of you. With fast turnaround times and clear, responsive communication, we make the entire headshot experience feel easy, supportive, and stress-free from start to finish.
Confident - Authentic - Unforgettable
PROFESSIONAL HEADSHOTS IN SAN DIEGO, AND SERVING NORTH COUNTY
WHY PEOPLE LOVE OUR
HEADSHOT PHOTOGRAPHY SERVICES
Cary produced quality, professional photos at a competitive price. I was very satisfied with the product and have gotten compliments on my photos. It is great to have professional photos on hand for LinkedIn and other various reasons in my line of work. Thank you Cary!
Paul DiPaolo
Cary is not only an incredibly gifted headshot photographer who takes amazing and beautiful photos but he is also very kind, sincere, and a consummate professional from the moment you meet him and throughout the whole time working with him. His fee and portrait prices are very reasonable and he gets your proofs to you in a timely manner. I loved all the photos he took, which made it very difficult to choose which ones to order. He is definitely a five-star photographer and I would highly recommend him to anyone.
Tina Pisciotta
Working with Cary was a very comfortable, fun and professional experience. We felt like we were with a friend from the start of the project to the end. The photos turned out lovely and we are very pleased. We needed an indoor studio and his Carlsbad photography studio was perfect for our shots. Hope to use him for outdoor takes someday! I recommend Cary Pennington Photography without hesitation.
Deborah
Not sure if we’re the right match?
Quality That Speaks for Itself
We don’t just take photos—we create images that connect. Every headshot is thoughtfully composed, professionally lit, and meticulously edited to bring out your best. From skin tones to backgrounds, we obsess over the details so your final images feel polished and powerful—never overdone.
Coaching That Feels Easy
(Even If You're Camera Shy)
Not sure what to do with your hands? Don’t worry—we’ll walk you through every pose, expression, and angle. We give clear, kind direction so you feel confident, not awkward. The goal? A relaxed, natural look that still feels elevated and professional.
Experience You Can Count On
With over 20 years of photographing professionals—from entrepreneurs to executives—we know how to adapt to you. Whether it’s your first headshot or your fifth rebrand, we make the process smooth, comfortable, and efficient.
Fast Turnaround, No Compromise
We know you’re busy, so we deliver your final retouched images within 72 hours or less—without cutting corners. Quick, consistent, and high-quality. That’s the standard.
WHAT SETS US APART?
Glad to meet you!
Cary Pennington, owner and professional photographer
Hey, I’m Cary—your go-to photographer in San Diego. I’m all about helping real people feel confident and comfortable in front of the camera. Whether you need professional headshots, branding portraits, or just a fresh image that actually looks like you, I’m here to make the experience feel relaxed, easy, and even fun. I specialize in headshots and branding photography for professionals, creatives, and small business owners throughout San Diego County. So if you’ve never loved a photo of yourself—let’s change that, with zero pressure, a little laughter, and images that feel like the best version of you.
WHERE WE CAN HELP
Brand Photography
Branding photography is more than pretty pictures — it’s your story, your personality, and the way clients connect with your business.
As a San Diego branding photographer in Carlsbad, I create authentic images for entrepreneurs, small businesses, and creatives. From lifestyle portraits to product photos, your branding session will give you visuals that feel real, look polished, and help you stand out online.
headshot photography
Your headshot should show confidence, style, and personality — not stiff poses.
As a San Diego headshot photographer based in Carlsbad, I create professional headshots that feel natural and approachable. Whether you need corporate headshots, LinkedIn photos, or personal branding portraits, every session is relaxed, collaborative, and designed just for you.
Because great headshots don’t just look good — they open doors, build trust, and help you stand out.
Family Photography
As a San Diego and Carlsbad family photographer, I love capturing the real stuff — the laughter, the snuggles, and even the beautiful chaos that makes your family yours.
Whether we’re at the beach, your favorite park, or cozy at home, sessions are relaxed, playful, and stress-free (toddlers included!). My goal is to document those genuine connections — the little moments that make your story unforgettable — so you’ll have a time capsule of love to look back on for years to come.
TESTIMONIALS
If I could give Cary 100 stars I would! Throughout the years I have had different needs for a photographer and Cary has been my go to for them all, headshots, family photos and most recently my wedding. He is worth every penny!!!! He’s kind, sweet, creative, and over-the-top with his customer service. I seriously have endless words of gratitude for this man and his talents. The best part about working with Cary is his patience so if you have a request he will make sure that you are 110% satisfied.
Jennifer Casey - San Diego, CA