Hi, I'm Kenny Nakai.
As a Chicago wedding photographer, I’m lucky enough to document some of the city's most beautiful love stories.
I hope you find inspiration here and connect with the feelings I had when I created each photo.
Hi, I'm Kenny Nakai.
As a Chicago wedding photographer, I’m lucky enough to document some of the city's most beautiful love stories.
I hope you find inspiration here and connect with the feelings I had when I created each photo.
A headshot that
actually looks
like you.
Real expressions. Real light. A real person behind the camera. Professional portraits for professionals who are tired of looking stiff, staged, or worse: AI-generated.
Individual & Team Sessions · Chicago, IL
Studio & on-location · All industries
What most people say before booking
"Honestly, I've been using the same headshot for
ten years."
"I've just never prioritized getting a new one. I've been using my wedding photo. Or a cropped group shot. Or something I took on my phone that kind of works."
Most people don't have an updated headshot. Some have never been photographed professionally. For others, it has been ten years. It falls to the bottom of the priority list. And then a job search starts, a promotion is coming, a new website is being built, and suddenly the photo matters. That's when most people call. Here's how I make it easier than you're expecting.
A headshot vs.
a branding session.
Here's the difference.
A headshot is a photo of a face. Good angles, confident expression, a presence that says you're approachable and professional. A branding session is about the full vibe of who you are and what you do. Most people need one. Some people need both.
OPTION ONE
The Headshot
A focused session producing clean, confident portraits for LinkedIn, your bio page, your website 'about me', or anywhere you need to represent yourself professionally.
OPTION TWO
The Branding Session
A through session building a library of images that reflects who you are, what you do, and the feeling your business creates. Consistent with your website, your logo, your whole client experience.
What makes a
headshot session
with me different.
I bring 19 years of experience as a family, engagement, and wedding photographer into every headshot session. That matters more than you'd think. The same skills that help a nervous bride relax in front of a camera are the same skills that help a professional look comfortable and confident in a portrait.
01
We take our time.
We take a lot of photos. We try a lot of poses. We review as we go on a laptop so you can see what's working and what isn't. Most people realize mid-session that it's not that they aren't photogenic...it was the angle, the expression, or the light. Once we find a version that works, we build on it.
02
We find your best angle.
Everyone has flattering and unflattering sides. And almost no one knows theirs. That's my job. I work with you to find the angle, expression, and posture that feel most like you at your most confident. When you see the photos, you'll know.
03
We match the photo to the message.
A financial advisor needs something different than a fashion-forward hair salon. A doctor needs something different than a creative entrepreneur. Before we shoot, we talk about where the photos will live, what they need to do, and what feeling they should convey. Everything after that serves that goal.
04
Studio or on location. Your call.
I shoot both. Studio gives us a controlled environment with clean backgrounds and precise light. On-location gives us vibe, context, and storytelling. I have the experience to make either work. I'll help you figure out which makes sense for how you plan to use the photos.
05
We think about where the photo lives.
A LinkedIn photo is a different photo than a branding website hero image. They can come from the same session. But they're framed, cropped, and styled with different intentions. During our shoot, we build in a variety of options so you have flexibility for LinkedIn, Instagram, your website, press, and whatever comes next.
06
Retouching that stays honest.
We can clean up flyaway hairs, temporary blemishes, fabric wrinkles, or hair placement. We can soften wrinkles that the camera overemphasizes. But we don't reshape your face or alter you into someone you're not. The goal is accuracy. Just your best, most confident version on your best day. Not a different person.
It's still
a real photo.
That still matters.
AI-generated photos are everywhere now. Upload a selfie, wait a few minutes, and download a polished portrait. The results can be convincing. They can also be sterile, off-putting, and most importantly, not actually you.
There's something uncomfortable about an AI headshot that's hard to name. The skin looks too smooth. The expression looks composed rather than captured. Something about the eyes feels just slightly off. People notice, even when they can't articulate what they're noticing.
My work is real. It's your real smile. Your real laugh. A real version of you on the day we actually met and worked together. Imperfections are what make people people. In a world of AI everything, a real photograph is starting to feel like a quiet luxury again.
This applies to everything I do. Weddings, engagements, family portraits, headshots, branding, commercial work. No AI generation. No fabrication. Just you, in a real room, on a real day, with a real photographer who has been doing this for years.
A range of industries.
Every kind of professional.
I've photographed professionals across a wide range of industries. Each has its own visual language. Part of my job is matching the photo to that language, not imposing one style on everyone.
Real Estate & Finance
Clean + Confident
Real estate teams, investment firms, financial advisors. Professional presence, consistent team grids, approachable but credible.
Medical & Legal
Approachable + Authoritative
Doctors, attorneys, consultants. Portraits that communicate expertise and warmth. The balance that earns client trust.
Creative + Fashion
Editorial + Expressive
Hair salons, designers, authors, agencies. More fashion-forward approach, almost like a magazine shoot. Style matched to brand.
Weddings + Events
Vendors + Planners
Wedding planners, stylists, event coordinators and their teams. Branding that matches the level of the clients they serve.
Entrepreneurs
Personal Branding
Founders, consultants, small business owners building a personal brand. Branding sessions that produce a full library of usable images.
Corporate Teams
Consistent + Efficient
On-site team shoots, 15–30 minutes per person, consistent backgrounds and lighting across every employee. Unified team presence.
ONE SESSION THAT STANDS OUT
A Lincoln Park hair salon —
photographed
like a magazine shoot.
One of the most memorable branding sessions I've done was for a modern, fashion-forward hair salon in Lincoln Park. They are experts at the latest techniques, the trending styles, the whole aesthetic of what's current in their industry.
For their branding photos, we went fashion-forward — almost editorial, like they belong in magazine. The goal wasn't a traditional team grid. It was matching the photos to the energy of their brand.
That's the difference between a headshot and a branding session. A headshot captures a face. A branding session captures an identity. When it aligns with everything else the business is already doing, it works harder than any individual portrait ever could.
WHERE TO NEXT
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I'm Kenny Nakai, a Chicago headshot and branding photographer creating modern, professional portraits since 2007. For executives, founders, and creatives who want to look confident, approachable, and unmistakably themselves.
