Let's be honest: most executives don't wake up excited about getting their photo taken. You're here because you need updated images, not because this is your idea of a good time.

That's completely normal. This guide will walk you through everything—what to bring, what to wear, and what to expect—so you can show up prepared and let me handle the rest.

TL;DR

Bring:

• 2–3 complete outfit options (shirt + layer + accessories)

• One structured layer (blazer, jacket, tailored cardigan)

• Backup basics (solid tees, simple shells)

• Accessories you actually wear

Colors: Rich, saturated tones work best. Avoid bright white and busy patterns.

Day before: Hydrate. Get decent sleep.

Session length: 60–90 minutes

What's in frame: Chest up for portraits (pants don't matter). For Brand shoots

Gallery delivery: 12–24 hours

First, About That Camera Anxiety

You might be dreading this a little. Most people are.

Here's what I need you to know: I do this every day. I've photographed hundreds of executives who walked in feeling exactly like you do right now. We're going to get the shot.

The best portraits happen when you're comfortable enough to stop thinking about the camera. My job is to get you there through direction, conversation, and creating an environment where something real can happen.

You don't need to perform. You don't need to know your angles. You just need to show up.

What You're Walking Away With

Every session delivers two kinds of portraits:

The Boardroom Portrait: Polished, professional, traditional. The image that satisfies your PR team, LinkedIn, and the conference speaker page. You need this one to check the boxes.

The Editorial Portrait: Human, honest, personality-driven. The image that makes someone want to meet you before you've said a word. This is the one that actually does work for you.

Somewhere in the session—between the formal poses and the "professional" expressions—something real is going to happen. A moment where you forget you're being photographed. That's the image I'm watching for the whole time.

Wardrobe: The Part You're Actually Worried About

Start With Your Goal

Think about the energy you want these images to carry:

• "I need to look like someone investors would trust with $50M"

• "Competent and in control, but clearly has a sense of humor"

• "I want my team to see me as more approachable"

If you're not sure, we'll figure it out together. But coming in with even a loose idea is helpful.

What to Bring

• 2–3 complete looks — the more options, the better

• One structured layer — blazer, jacket, or tailored cardigan

• Backup basics — solid tees, simple shells that work under layers

• Varying necklines (if applicable) — gives you gallery variety

• Accessories you actually wear — watch, glasses, jewelry, scarf

• Lip balm if you tend to run dry

Pro tip: Wear one outfit to the session. Bring the rest on hangers.

What's Actually in Frame

Executive portraits are chest-up. Your pants, shoes, and whatever else is happening below the frame? Doesn't matter. Sweatpants are welcome. I'll never tell.

Color Guide

This is where people overthink it. Here's my actual philosophy: wear colors you love.

I don't have a list of "approved colors." What works depends on your skin tone, your eye color, your hair, and—most importantly—your brand. A founder in fintech and a creative director at a design agency shouldn't show up in the same palette. If you are unsure, just ask.

The One Hard Rule

Avoid bright white. It pulls focus from your face and competes for attention under studio lights. Off-white, cream, ivory—all fine. Ideally not stark white.

The Ratio Principle

Bold colors can absolutely work—it's about how much of that color shows up in frame relative to everything else.

Example: A neon pink shirt with nothing over it? The pink becomes the star of the image, pulling attention from your face. That same shirt under a dark blazer? Now it's just a sliver of color peeking through—an accent, not a distraction. Layering gives you control.

The Balance Rule

If you're bringing something bold or unexpected, also bring a neutral backup. If your wardrobe runs conservative, throw in one piece that's a small stretch. We'll figure out the right balance together once you're here.

Colors and textures you love can lead to a really cool final image—so don't play it too safe. Bring options. We'll decide together.

Fit

If something fits almost right, bring it anyway. We can pin or tape the back so it looks perfect on camera.

Hair and Makeup

I don't offer styling services in house, but I can recommend people if you'd like professional support.

If you want a stylist: Mention it when you book so we can coordinate timing. For longer sessions, we can arrange for them to come to you.

If you're handling it yourself: Show up groomed the way you'd show up to an important meeting. That's the standard.

The Day Of

Day before:

• Hydrate well (your skin will thank you)

• Get decent sleep

When you arrive: Bring your wardrobe options. We'll review everything together before we start shooting.

During the session: I'll direct you through angles and expressions. We'll check images together throughout so you're never in the dark about how things are going.

One thing: We are on the same team, so if something's not working—the color, the fit, the direction—just let me know so we can pivot. The best portraits come from collaboration. We will adjust in real time together.

Location

My studio is in Adams Point, Oakland. For larger shoots or on-location work, I come to you.

I regularly photograph executives throughout San Francisco, Silicon Valley, Palo Alto, San Jose, and the greater Bay Area.

FAQ

How long until I see my images?

Your gallery is typically ready within 12–24 hours.

How many final images do I get?

This depends on your session type and package. We'll confirm specifics when you book.

Do I pick the final images myself?

Yes, selection is on your end. That said, I'm more than happy to weigh in. Just send me your top picks before you finalize and if I think there's a stronger option, I'll tell you.

Is retouching included?

Yes—and it's the same high-end treatment celebrities get for magazine covers. I retouch by hand, removing distractions (blemishes, stray hairs, tired eyes) while preserving the skin texture that makes you look human. As AI-generated perfection floods the market, 'real' has become a status signal. Your image should prove there's a person behind the title.

What does retouching include?

Color correction, exposure balancing, blemish removal, under-eye circles, stray hairs. No face reshaping. No artificial smoothing. You'll still look like you—just the version that got a full night's sleep.

Can I use these images anywhere?

Yes. Your images are licensed for personal and professional use: LinkedIn, website, press, speaking engagements.

What file format will I receive?

High-resolution JPEGs suitable for print and digital use.

What if I need to reschedule?

I ask for at least 48 hours notice. Cancellations inside that window may forfeit the deposit, though I'm reasonable about genuine emergencies. Just communicate early and we'll figure it out.

How far in advance should I book?

For executive sessions, 1–2 weeks is usually fine. If you have a specific deadline (board meeting, funding announcement, conference), let me know and I'll accommodate.

Do you offer rush delivery?

Yes. If you need images faster than my usual turnaround, just let me know when booking and we can discuss.

What's the difference between a headshot and an executive portrait?

A headshot is a shoulders-up photo for identification. An executive portrait is editorial craft applied to professional photography—the same quality you'd see in a magazine, built around who you actually are. Every session delivers both: a boardroom-ready image and an editorial portrait with real presence. Polished enough for investors. Human enough to be remembered.

What's the difference between corporate headshots and editorial portraits?

Standard headshots prioritize safety and "professionalism". They're designed to fit within a brand or team page. My Editorial portraits prioritize character and distinction—they're designed to stand on their own and tell a story. My sessions deliver both.

Do you travel for sessions?

Yes. Based in Oakland, but I regularly work on-site throughout San Francisco, Silicon Valley, and the Bay Area. Travel fees apply.

What should founders know about executive portraits?

If you're raising capital, looking "safe" isn't enough. You need to look like a bet worth making. We'll lean harder into the Editorial Portrait: less stiff blazer, more character. You're not just managing the present. You're selling the future.

Questions before your session? Reach out.

Brian DeSimone is an executive and editorial portrait photographer based in Oakland, California. With a background in hospitality and over two decades behind the camera, he's photographed hundreds of founders, C-suite executives, and creative teams throughout San Francisco, Silicon Valley, and the Bay Area. His specialty: directing people who aren't used to being directed, and making it look natural. Corporate portraits, teams and executive headshots that are polished enough for the boardroom, human enough to be remembered.