This guide will walk you through everything - what to bring, what to wear, and what to expect. Show up prepared and let me handle the rest.

TL;DR

Bring:

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

• Layers! At least one structured (blazer, jacket, cardigan, etc)

• Backup basics (solid tees, simple shells, various neck lines)

• Accessories you actually wear (neck-ties, necklaces, earrings, etc)

Colors:

Think about your brand first. Neutral tones and not overly saturated colors are safe. Rich saturated colors that work with your skin tone, hair and eye colors also look great but bring layers! Avoid bright white and busy patterns (unless thats your vibe).

Day before:

Hydrate. Get decent sleep.

Grooming + Makeup:

Show up groomed and feel free to bring your backup supplies so we can do touch ups along the way if needed.

Wardrobe

Start With Your Goal

Think about the people you are trying to signal to and 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"

• "I want to be unapologetically me!"

If you're not sure, let's figure it out together.

What to Bring

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

• 1-2 structured layers — blazer, jacket, or tailored cardigan

• Backup basics — solid tees (if thats your style) or simple shells that work under layers

• Varying necklines (if applicable) — especially for women

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

• Lip balm if you tend to run dry

Pro tip: Wear one outfit to the session.

Color Guide

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 likely want to project different things. If you are unsure, just ask.

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

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.

The One (Mostly) Hard Rule

Avoid bright white unless totally necessary. It pulls focus from your face and competes for attention under studio lights. Off-white, cream, ivory—all fine. Ideally not stark white, but I can honestly make anything work.

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 Before

• Hydrate well (your skin will thank you)

• Get good sleep

The Day Of

When you arrive: Bring your wardrobe options. We'll review everything together and get strategic 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 unsure about how things are looking.

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 24-48 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, but I'm thrilled to weigh in. You can send me your top choices 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 and details 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 file format will I receive?

High-resolution JPEGs for most people. But if you need a TIFF, or anything else, I am happy to provide.

What if I need to reschedule?

I ask for at least 72 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?

It really depends on the season. For executive sessions, a minimum of 1–2 weeks could work. 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 whats possible.

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

A headshot is a basic, shoulders-up photo for work identification. You can use your iphone or any number of A.I. services to get this done, cheap.

My executive portraits are more strategic and have a thoughtful process built around your goals and personality. It's editorial craft applied to professional photography—the same quality you'd see on the cover of a magazine. 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.