How often should I update my headshot?
This is a very common question.
Often I hear, but I like my last headshot.
Do you? Or do you like how you looked then and be honest, do you still look like that? If you met someone in person would they whisper, nice photo but that looks like a younger version….
So, with that being said, you should probably think about updating your headshot every year or two (at the most.) I
Consider updates when hairstyles, colors, or weight change noticeably, or when your career path shifts. Industry standards also play a role; some professions require more frequent updates than others. Ultimately, a fresh headshot maintains a relevant and professional online presence.
Why Your Headshot Matters More Than You Think
Your headshot is often the first thing people see—on LinkedIn, your website, or even a conference program. It should instantly communicate confidence, professionalism, and personality. If your current headshot is outdated, poorly lit, or just doesn’t feel like you, it might be sending the wrong message. A high-quality, authentic headshot helps you stand out, make meaningful connections, and build trust before you even say a word.
But a great headshot is more than just a nice photo—it’s a personal brand statement. The right lighting, angles, and expression can showcase your expertise and approachability in a way that feels natural and effortless. Whether you're an entrepreneur, executive, or creative, your headshot should reflect not just who you are today, but where you're headed. It’s not just a photo—it’s an investment in your success.
What to Wear for Your Brand Session: The Secret to Loving Your Photos
The biggest concern for my clients is: what to wear for a brand session.
If you’ve ever thought about booking a session but hesitated because you’re paralyzed about what to wear. But you know, you’re not alone.
But here’s the thing: it shouldn’t stop you from doing something amazing for your business.
The Magic of an Outfit That Feels Like YOU
What I’ve noticed about all the brand sessions I’ve done for my clients is that there’s always one outfit that ends up being their favorite. Every. Single. Time.
And guess what…
it’s jeans and a T-shirt. 🤪
Are you surprised?
Why Jeans and a T-Shirt Work Might Work for Your Brand
It’s authentic.
It matches your brand vibe and personality
It still has personality.
What Does That Look Like for YOU?
Maybe jeans and a t-shirt won’t work for your session? The key is to choose something that feels most like YOU.
For example:
Tailored jeans and a blazer if your vibe is polished but approachable.
Leggings and a crop top if you’re all about an active, high-energy brand.
A bold, structured dress if you want to make a statement.
Whatever it is, it should feel like you’re showing up as your most authentic self.
Why Variety Still Matters
Include one outfit in your session that feels like you on a great day. The outfit that feels the most comfortable, authentic, and “you.”
Need More Outfit Inspiration?
If you’re still stuck on what to wear, I’ve got you covered. I have a Prep Guide that I send along with your session appointment confirmation. They are not hard fast rules, merely suggestions. I encourage you to spend some time planning your clothing for your branding session. The key is that whatever you wear, it makes you feel amazing.
Your brand session is about showing the world who you are—let’s make it feel effortless.
25 Years in Business!
Nina Pomeroy Agency Inc. Celebrates 25 Years of Excellence in Luxury Headshot and Branding Photography
Pleasanton, CA – Nina Pomeroy Agency Inc., a premier luxury headshot and branding photography studio in downtown Pleasanton, celebrates 25 years of excellence and has set the professional standard for modern business headshots.
Pomeroy works with executives, actors and brand-conscious professionals in real estate and finance, helping them elevate their brands and make lasting impressions with premium headshots.
With unauthentic AI-generated images on the rise, Pomeroy brings over 25 years of experience to the Bay Area delivering carefully crafted images that represent her client’s personality, authenticity and professional essence — something AI simply cannot replicate.
With over 425 five-star Google reviews, Pomeroy is known for her personalized coaching and direction in every session, whether in her studio or on location. Clients receive expert guidance to showcase their personality and confidence, creating impactful images that leave a lasting impression.
In addition to her photography work, Nina Pomeroy is a best-selling author of OWN IT: The Essential Guide to Crafting Your Authentic Personal Brand, further solidifying her expertise in helping individuals present themselves with confidence and genuine impact.
Beyond her work in photography and branding, Pomeroy also curates exclusive private trips and workshops to Tuscany, Italy, featuring personal brand photoshoots, private food and wine excursions, and accommodations at an award-winning boutique hotel.
As the agency celebrates this significant anniversary, it continues to uphold its dedication to providing unparalleled photography services, ensuring each client receives a bespoke experience and exceptional imagery that stands the test of time.
About Nina Pomeroy
Nina Pomeroy Agency Inc is a luxury brand specializing in headshots and branding photography. With over 25 years of experience creating high-end imagery, Pomeroy is trusted by top professionals to elevate their brands and make powerful visual statements – worldwide.
25 Year Anniversary Celebration!
This milestone isn’t just a number—it’s a reflection of growth, real connections, and the power of showing up authentically. I am excited to share that I am celebrating 25 years since starting my photography business in New York City.
From travel photography to families and weddings, and now headshots and branding, this journey has been incredible. I’ve met amazing people, heard inspiring stories, and built a community that keeps me evolving.
25 years as an entrepreneur and now a global business, this is just the beginning! I’m beyond grateful for every client, comment, and connection that has shaped my journey.
If you’re starting out or feeling stuck: Show up. Share your story. Build real connections.
Thank you for being part of this adventure—let’s keep creating together!
Hire Nina Pomeroy for Speaking Engagements
🎤 Speaking Engagements
Need a captivating speaker to inspire and energize your next event, workshop, or mastermind? From keynotes and panel discussions to interactive training sessions, I deliver actionable insights designed to make a lasting impact on your audience.
My signature talks cover topics like mastering your niche and harnessing the power of personal branding. Your audience will walk away with clarity, confidence, and practical strategies they can put into action right away.
The Value of Investing in Headshot Photography
We’ve all heard the saying, “Buy nice or pay twice,” and it couldn’t be more true when it comes to investing in headshot photography. Choosing the cheapest photographer often means sacrificing the quality and professionalism that are essential for creating a professional portrait. first impression. While it might feel good to save a few dollars upfront, those savings can quickly disappear when you realize your photos don’t meet your needs or reflect your best self.
Things to research when picking a headshot photographer:
Portfolio and Style: Review the photographer's portfolio to get a feel for their style and quality of their work. Look for consistency in the style of headshots they produce and ensure it aligns with the image you want to portray.
Experience and Specialization: Determine the photographer's level of experience and whether they specialize in headshot photography specifically. Experience in this niche can result in more polished and effective headshots.
Reviews: Read reviews from past clients to get insights into their experiences working with the photographer. Look for feedback on professionalism, communication and satisfaction with the final results.
Location and Studio: Consider the location of the photographer's studio and whether it is convenient for you. For your safety amongst other things you don’t want to go into a stranger’s home or garage.
Turnaround Time: Inquire about the photographer's turnaround time for delivering the final edited images. Depending on your timeline, you may need quick delivery of the photos for professional or promotional purposes.
Satisfaction Guarantee: Will they guarantee that you’ll be 100% happy with the results of your photoshoot?
Rest assured, I guarantee your satisfaction - failure is not an option!
A high-end headshot is an investment in your future and your goals. Whether it’s for your professional profile, acting portfolio, or personal branding, choosing a headshot specialist brings confidence, authenticity, and value. The next time you’re faced with the choice between price and quality, remember: a wise investment today saves you from paying twice tomorrow.
Should I have a more creative headshot?
When it comes to headshots, the choice between a creative or corporate style depends on how you want to present yourself professionally. Corporate headshots are timeless and polished, perfect for industries like finance, law, or real estate, where professionalism and trust are paramount. On the other hand, creative headshots let your personality shine—ideal for entrepreneurs, creatives, and anyone in industries that celebrate individuality.
Think about your audience and goals. If you're networking with corporate professionals or applying for traditional roles, a clean, professional look may be your best bet. However, if you’re a writer, actor, or entrepreneur aiming to stand out, a creative headshot can highlight your unique style while still being professional. It's all about finding the balance between showcasing your personality and aligning with your industry’s expectations.
The beauty is, you don’t have to pick just one! Many people have both styles in their portfolio so they can tailor their image to different opportunities. Whether you go for a sleek corporate vibe, an artistic flair, or both, your headshot should feel authentic and empower you to show up as your best self.