Creative Headshots That Feel Natural, Look Professional, and Show Off the
Real You
I work with professionals across Carlsbad and San Diego to create modern headshots and branding images that reflect who you are — and where you're going. Because a good headshot doesn’t just make you look professional — it makes people feel like they already know you. Whether it’s for LinkedIn, your website, or simply stepping into your next chapter with clarity and connection, I’m here to guide you through a relaxed, intentional experience that brings out the real you.
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Maybe you're building a brand, taking your career to the next level, or you're just tired of hiding behind that outdated photo.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
headshot photography
Whether you're a seasoned pro, a growing entrepreneur, or a creative soul carving your path — your image should reflect your confidence, style, and personality (without feeling stiff or overly posed).
As a headshot photographer, I specialize in capturing that sweet spot between professional and approachable. Whether we shoot in the studio or outdoors, the experience is relaxed, collaborative, and tailored just for you.
I believe great headshots are more than just a nice photo — they open doors, spark connection, and help people remember you. Let’s create something that feels real, looks amazing, and helps you show up with confidence. Let’s tell your story in one powerful frame.
Brand Photography
Branding photography isn’t just about pretty pictures. It’s about telling your story, showing your personality, and helping people feel connected to what you do.
Whether you’re building something brand new or refreshing an established business, I’m here to help you create images that feel authentic and intentional — visuals that speak directly to your dream clients.
From relaxed lifestyle photos to detail-rich product shots, every image is crafted with purpose — to reflect the heart of your brand and help you truly stand out.
Let’s create visuals that feel like you — and connect like crazy.
Family Portraits
As a San Diego family photographer, I’m here to capture the real stuff — the laughter, the snuggles, the chaos, and all the little in-between moments that make your family yours.
Whether we’re at the beach, your favorite park, or cozy at home, the experience is relaxed and fun (yes, even with toddlers!). My goal is to document those genuine connections — the kind that’ll make you smile now, and maybe tear up a little years from now.
Because this isn’t just about photos. It’s about remembering how it felt. Let’s create something beautiful together — a little time capsule of love.
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