Headshot Session FAQ

If you’re in need of a headshot or simply looking to update your professional profile, you may have a lot of questions about what to expect during the process. That’s why I’ve put together this comprehensive headshot FAQ to help you navigate the ins and outs of a headshot session with me.

From what to wear to how long a session typically takes, I’ve got you covered with all the information you need to make the most of your headshot experience. So, if you’re ready to feel confident and approachable in front of the camera, let’s dive in!


What Does a Headshot Session With Jason Look Like From Start To Finish?

If you’re wondering what to expect when you book a headshot session with me, here’s a quick rundown:
Reach out: First, get in touch with me using my contact form here. In your message, let me know a bit about your intended session so I can get an idea of the kind of headshots you want.
Schedule a Consultation: Schedule a consultation: After receiving your email, I’ll reply within 24 hours to set up an appointment for a quick phone or video call. During this consultation, I’ll ask you a few questions to better understand the details of your headshot session, so I can best help you get images you’ll love.
Reserve your Headshot Session Date: Once I gather all the details I need from our phone consultation, you can submit a deposit to secure your photoshoot date with me. 
 • Headshot Photoshoot: On the day of your photoshoot, I’ll guide you through poses and expressions that will capture your best self. Depending on the headshot style(s) you want and how many looks you want to achieve, a headshot session with me usually takes somewhere between 1 to 4 hours. I can give you a better idea of how long it will take after I learn more about what you  want at your consultation.
Choose your Favorite Photos: Shortly after your photoshoot I’ll provide you with a watermarked gallery of all the usable photos from your session, roughly edited with global adjustments only (no photoshop). From this gallery, you can then choose all the images you want me to edit for you. I’ll also give you my recommendations for the photos I like best.
Delivery of your Finished Images: Once you select your favorite images I will get to work editing your images. Once finished, your final image(s) will be delivered to you in both web optimized and full res Jpeg formats via Google Drive.

How Much Does a Headshot Session Cost?

Base Price is $275 and Includes:
Environmental style headshot session at your location
• Watermarked proofing gallery of all captures from your session
• Hand retouching of your favorite headshot by me
• Digital JPEG of your favorite image optimized for the web at 2000px on the longest side
Additional People / Images:
• 2-9 images: $220 per image
• 10-19 images: $195 per image
• 20+ images: $165 per image
Style Options:
• Environmental (within 1 hr of Sonoma CA): No additional fee
• Studio Style: $400 set up fee at your location
• On-site professional hair and makeup $250 per person

What Are The Different Headshot Looks I Can Get?

You can choose from three distinct styles: environmental, studio, and ring light headshots—each has its own strengths:

Environmental headshots use natural light and real-world settings for a relaxed, approachable look. They’re ideal for actors, realtors, entrepreneurs, or anyone wanting to show personality and warmth. They’re also a cost-effective option.
Studio headshots are clean and professional, taken in a controlled setting with a solid background. These work great for corporate or formal industries and are perfect if you want your headshot to blend seamlessly into your LinkedIn profile or website.
Ring light headshots are bold and creative, shot using my custom built 4ft by 4ft, 28 bulb ring light. This thing creates unique catchlight in the eyes that stand out—perfect for artists, creatives, or anyone who wants something modern and eye-catching.

What Are The Space Requirements For Studio and Ring Light Headshots At My Location?

To set up studio or ring light headshots at your place, I’ll need at least 12′ wide x 14′ long x 8′ high of open space. Think garage-sized or a roomy living room. Taller ceilings and light control help with style options, but they’re not essential.
I usually shoot with white, black, or muslin backdrops, but I’m happy to create a custom look if you have something specific in mind. If you’ve got the space, I’ll bring my mobile Sonoma County portrait studio to you.

Do I Need To Do My Own Make For My Headshot Session?

No, you don’t—but I highly recommend using a pro. Even if you’re great with everyday makeup, studio lighting is a different game. I’ve had clients use SPF foundation, which looked fine in person but created shiny hotspots in their photos. My professional hair and makeup artist knows exactly how to prep your look for the camera, so you’ll get the best headshots possible from your session.

What Should Women Wear For Professional Headshots

Here are a few simple rules that make styling your outfit way easier:

Start With The Location. Make sure to choose colors that will look good with the location of your headshot or the color of the studio backdrop.
Anchor Your Outfit To Your Jacket. A structured jacket adds polish, shapes your silhouette, and keeps the attention on your face. Choose one you love, then build your look around it.
Avoid Cheap Fabrics. Skip synthetics like polyester, rayon, or nylon. They reflect studio light and look like plastic in your final photos. Stick with wool, cotton, linen, or silk for best results.
Choose Timeless Colors. Navy, charcoal, grey, and blue flatter most skin tones and look great on any background. Earth tones like olive or tan can also work well.
Pick a Flattering Neckline. Your blouses neckline should settle no lower than an inch below your collarbone. Go for collared, jewel, crew, or shallow V-neck styles. Avoid deep plunge styles or wide neckline cuts designed to show more skin.
Long Sleeve Shirts Only. Sleeveless tops pull focus to your shoulders. Long sleeves keep the attention where it belongs—on your face.
Keep Jewelry Minimal. Earrings or a short necklace are fine, but avoid flashy pieces that steal the spotlight or get cropped.
Layer to Elevate. Even casual looks benefit from layering. Jackets not only add visual interest to your headshots, they also signal professionalism.
For More Detailed Information on what to wear for your headshot session, be sure to check out my post on what to wear for female headshots.

What Should Men Wear For Professional Headshots

Here are a few simple tips to help you dress better for your headshot:
Start With a Jacket. Layering is 80% of looking great. A well-fitted blazer or sport coat gives you shape, adds structure, and keeps the focus on your face.
Avoid Synthetic Fabrics. Cheap suits made from rayon or nylon photograph poorly and look like cheap plastic. Stick to natural fibers like wool or cashmere for a clean, professional look.
Pick Timeless Colors. Navy, charcoal, and gray are your safest bets. They flatter most skin tones, match nearly any shirt, and age well in photos.
Go With a Solid Shirt. White or light blue shirts work with all of the jacket colors mentioned and won’t compete with your face. Keep it simple unless you’re intentionally aiming for a bold look.
Use a Spread Collar. Spread collars are the most versatile and flattering option. They look good with or without a tie and frame your face well.
Buy Quality Shirts. Avoid “no-iron” or “moisture-wicking” shirts—they look shiny and cheap on camera. Choose 100% cotton with neck/sleeve sizing (not single sizing like medium). Avoid shirts with plastic buttons in favor of horn or mother of pearl.
Choose a Tie Based on Your Jacket. Only wear a tie if you’d normally wear one to a client meeting or interview. Stick to subtle patterns with a small splash of contrast (10–20%) if you’re a style noob.
Still unsure about what to wear? Check out this post about what to wear for male headshots to learn how to get the best headshot possible.

Where Does A Headshot Session With Jason Guy Take Place?

I offer on-location headshot sessions, which means that I come to you. Whether you’re based in Sonoma, California, or within an hour’s drive of my location, I can accommodate your headshot needs at no additional charge. This includes serving clients in Sonoma County, Marin County, Napa County, and the following Northern Bay Area cities:
American Canyon, Angwin, Benicia, Boyes Hot Springs, Calistoga, Cotati, Crockett, Dillon Beach, El Verano, Eldridge, Fairfax, Fairfield, Forestville, Glen Ellen, Green Valley, Guerneville, Healdsburg, Hercules, Inverness, Kentfield, Kenwood, Lagunitas, Larkspur, Martinez, Mill Valley, Napa, Novato, Occidental, Penngrove, Petaluma, Pinole, Point Reyes Station, Rohnert Park, Ross, San Anselmo, San Geronimo, San Pablo, San Quentin, San Rafael, Santa Rosa, Sausalito, Sebastopol, Sonoma, St. Helena, Tomales, Vallejo, Windsor, Woodacre.
For locations outside this area, I can still accommodate your headshot needs for an additional travel fee. The fee will be determined based on the specifics of the job, so feel free to reach out to me to discuss your needs.

How Long Should I Expect a Headshot Session With Jason To Take?

The short answer is it depends factors like: 
• The headshot style(s) you want (environmental or studio)
• How many looks you want
• Weather or not you want hair and makeup services for your photo shoot

For example, if  you’re a guy and you don’t need makeup and you want one headshot captured with an environmental background, I’d recommend you budget at least an hour with me around sunset for best results.

By contrast, if you’re a woman and want one of my hair and makeup artists to enhance your features prior to your photo shoot and you want studio style portraits, I’d allow at least 3 ½ to 4 hrs to get results consistent with what I show in my portfolio.

There are obviously endless scenarios I could outline here. That said, in most cases you’ll need to budget  somewhere between 1 to 4hrs (or more) depending on specifics. I’ll be able to give you a better idea of how long it will take once I learn more about your  intended  session.

Will You Show Me What To Do In Front of the Camera For My Headshot Session?

I believe that comfort in front of the camera is my job. Therefore, If you’re feeling nervous or shy, don’t worry – I’ll guide you through the process and make sure you feel at ease while you’re being photographed. In my view everyone has the potential to look confident and approachable in their headshot, regardless of their experience in front of the camera.

During your headshot session, I’ll offer plenty of direction and coaching to help you strike the right pose and convey the right message with your expression. I’ll work with you to find the best angles and lighting that compliment your features and bring out your best self. Whether you’re a seasoned model or someone who’s never had their photo taken before, my goal is to create the best profile photo you’ve ever seen of yourself. So if you’re feeling a bit camera-shy, don’t worry – I’m here to help you every step of the way!

How Many Different Looks Can We Do?

I’m happy to do as many outfits changes as you’d like during your photo shoot without any extra charges. The final cost of your session isn’t based on how many outfit changes you make, but rather on how many images you choose to purchase from your photo shoot.
This means that you can mix and match different outfits and backgrounds to create a diverse range of looks. Please feel free to bring all the options you think you might want to be photographed in so we can work together to create headshots that showcase your personality and unique style!

Can I Wear Glasses In My Headshots?

Yes—but with one important caveat. Lenses reflect studio light and can block viewers from connecting with your eyes. To avoid this, bring glasses without lenses. If removing the lenses isn’t an option, consider picking up an inexpensive frame from somewhere like Zenni before your session. It’s a small fix that makes a big difference.

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