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What to Wear for Professional Headshots: A Chicago Photographer’s Guide

Wear a solid, mid-tone color in a fabric that isn’t shiny — navy, charcoal, olive, burgundy, or deep teal all work. Skip logos, busy patterns, and pure white. Choose a neckline that frames your face rather than competing with it. If you’re unsure, bring two or three options and we’ll decide together at the studio. […]

How Much Do Headshots Cost Chicago? | Pricing Guide

If you’ve been looking into headshots, you’ve probably noticed how wide the range is. You can find someone offering a quick session for $50. You can find photographers charging several hundred dollars. And then there are full personal branding sessions that go well beyond that. At first, it feels inconsistent. But it isn’t. It comes […]

Best Locations for Actor Headshots in Chicago | Studio vs Outdoor

If you’re an actor in Chicago, you’ve probably wondered: “Where should I take my headshots?” It’s one of the most common questions I get. And on the surface, it makes sense — Chicago has incredible neighborhoods, architecture, and backdrops. But after photographing actors across the city for years, I can tell you this: The location […]

Why Are People Still Searching for “JCPenney Headshots”?

Every year, thousands of people still search for “JCPenney headshots.” Not “executive portrait photographer.” Not “personal branding photography.” Not even “professional headshot studio.” Just JCPenney. That search isn’t really about a department store. It reflects how many professionals still think about headshots. For a long time, a professional photo was simply something you checked off […]

What Chicago Casting Directors Look for in Headshots

Most actors I work with in Chicago aren’t worried about looking attractive on camera. They’re worried about something deeper: Does this actually feel like me? And will casting see me the way I want to be seen? That’s the part that doesn’t always get talked about. Casting directors aren’t searching for the most dramatic image, […]

Professional Headshots vs AI Headshots: What Trust, Emotion, and Experience Still Require

AI headshots are becoming increasingly common. They’re quick, polished, and marketed as an easy alternative to traditional photography. For many people, they feel like a practical shortcut—especially in a professional world that moves fast. But headshots have never really been about speed or convenience. They’re about perception. After years of photographing professionals across industries, one […]

Creative Headshots to Showcase Your Unique Style and Personality

If you’ve ever looked at your LinkedIn photo and thought, “This doesn’t really look like me… or at least the version of me I want people to see,” you’re not alone. More and more professionals are moving away from stiff, traditional headshots and choosing something with personality—creative headshots that feel modern, expressive, and unmistakably you. […]

Professional Photography Guide

 Professional Photography Guide Are you ready to capture your best professional self? Welcome to our guide on professional photography, where we’ll explore everything you need to know about perfecting your image with expert headshots. Whether you’re an aspiring actor, a seasoned professional, or part of a business team, a quality headshot can make all the […]

Business Portrait Photography: A Key to Professional Branding Success

Business portrait photography, corporate team photos, and business marketing photography are essential to your company’s success in their own unique ways. Kyle Bondeson Photography understands the importance of high-quality photos that accurately reflect your personality, your business culture, and your brand.  We can help you with all your business marketing photography needs, whether you run […]

Corporate Event Photos: Capturing Key Moments at Business Milestones

Capturing key moments and milestones is important for businesses of all sizes. Not only does it help with marketing and promotion, but it can also help you capture the attention of sponsors, partners, and investors. Kyle Bondeson Photography offers exceptional corporate event photo shoots designed to capture the excitement and passion of the moment for […]

Why a Professional LinkedIn Headshot Beats the Best AI Generators

LinkedIn is a professional social media platform that brings recruiters, companies, and job seekers together in one place to learn, collaborate, and network. With it, you can build relationships with others in your industry, meet people from different parts of the world, and communicate with people who work with major companies. In order to use […]

Choosing the Best Camera for Headshot Photography

Snapping an incredible headshot requires professional equipment, from the cameras and lenses to the backdrop and lighting. Any camera can produce a headshot, if you want the best photography possible, it is important to focus on a few key considerations. Choosing the best camera for headshot photography leads to top-notch results that improve the quality […]

The Best Professional Headshot Background for Your Resume, Website, and More

A successful professional headshot is the result of numerous factors, including your facial expression, your clothing and accessory choices, and even the background. Headshot backgrounds can change the mood of your photograph, and they can vary based on your company’s industry and role.   Kyle Bondeson Photography offers corporate headshot packages that suit your needs […]

How to Choose a Photographer

In today’s competitive professional world, photography is vital for your personal brand. Many professionals are unsure about how to choose a professional photographer for business, actor, or staff headshots. Kyle Bondeson Photography has put together a list of tips and tricks to help you choose a photographer that will provide quality photos that suit your […]

Your Guide to Incredible and Professional Realtor Headshots

As a Realtor, your headshot is a powerful marketing asset that can help you make great first impressions with potential clients. Your Realtor headshot should represent you as a whole – what you look like and what you stand for. At Kyle Bondeson Photography, we understand that your headshot represents your commitment to your clients […]

How Corporate Headshots Can Enhance Your Personal Branding

Branding involves creating a unique visual identity for your business and the product or services you provide. While many businesses focus on logos, fonts, and color palettes, your corporate headshot is often the most memorable part of your marketing. Exceptional corporate headshot photography can enhance your resume, assist you with networking, or even add the […]

Why Is It Important to Do Staff Photos?

It can be easy to forget in today’s digitized business world that companies are ultimately made up of a group of individuals working together toward common goals. More companies are offering remote and hybrid working options, which can make it harder to remember humans are behind their success. Staff photos are a great way to […]

Headshots Outside or Inside: Which is Better?

Headshots are tightly cropped portraits that only include the head and shoulders of the subject. The focus is entirely on the person’s face. That may sound faintly similar to a passport photo or even a mug shot. However, a professional headshot is much more than just a quick snapshot. A professional headshot will reveal your […]

How Should Staff Prepare for a Business Photo Shoot?

Employee photos are an exceptional tool if you want to enhance your brand image or just show off your company to potential clients. A business photo shoot and staff headshots can provide a professional company impression. To have a great business shoot will require planning, persistence, and flexibility. And you’ll also need an experienced professional […]

What is Personal Branding Photography?

If you’ve been in the business world for even a short time, you may have heard someone say that you need to know your own personal brand. With the rapid growth of social media, the gig economy, and digital dominance, personal branding photography is becoming an essential element for those who desire a successful career. […]

Why Do Medical Schools Ask for Headshots?

Why Am I Being Asked for Headshots for Med School? Many documents are required when applying for admission to upper-level academic institutions and programs. Applying for med school involves completing a series of documents, and you’ll be asked to include a recent photo with your application. Since you are trying to make a good impression […]

Portrait vs. Headshot: What’s the Difference? (2026 Guide)

A headshot is a close-up, professional photograph — head and shoulders, face filling the frame — used for LinkedIn, company bios, and actor portfolios. A portrait is broader and more artistic: it can show more of the body, include multiple people, and convey personality or story. The main difference is purpose: headshots introduce you professionally; […]

Realtors Marketing Without Headshots: Is It a Good Idea?

Real estate professionals do a lot more than help their clients buy or sell properties. They must sell their personal brand. Buyers and sellers have lots of options when choosing a real estate agent. Branding and marketing strategies can help you stand out and show clients you are your best choice. Realtors marketing without headshots […]

What is a Headshot?

What is a Headshot? Defined There are many terms in the photography business, and it may seem a bit confusing at first. One such term is ‘headshot,’ which instantly conjures an image in your mind, but is it the right one? No matter what you think a headshot is right now, we’re going to explore […]

Who Needs Professional Headshots? Do I Need One?

You might be wondering if your profession requires you to get a professional headshot. Even if it doesn’t, you’d be in a better position if you decide to get a headshot anyway. After all, there are many, many reasons to have a nice, professional photo of yourself taken. Everyone from the CEO to the janitor […]

What to Wear for Professional Headshots: A Chicago Photographer’s Guide

Wear a solid, mid-tone color in a fabric that isn’t shiny — navy, charcoal, olive, burgundy, or deep teal all work. Skip logos, busy patterns, and pure white. Choose a neckline that frames your face rather than competing with it. If you’re unsure, bring two or three options and we’ll decide together at the studio.

People decide how they feel about a face in about a tenth of a second. That’s not a marketing line — it comes from a Princeton study by Willis and Todorov published in Psychological Science, which found that impressions of trustworthiness and competence form after roughly 100 milliseconds of exposure.

Which tells you what your outfit is actually for.

It isn’t there to be noticed. It’s there to stay out of the way so your face gets that tenth of a second uninterrupted.

Almost every wardrobe question I get has the same answer underneath it: does this pull attention toward your face, or away from it?

What should you wear for a professional headshot?

Solid colors. Mid-tones. Clean lines. Nothing that reflects light or creates a pattern the camera has to fight.

That’s the whole framework. Everything below is just detail.

I’d also say this, because most people arrive worried about it: you don’t need new clothes. The best headshot outfits are usually things people already own and already feel like themselves in. Comfort reads on camera. Stiffness reads on camera too.

What colors photograph best?

Mid-tone colors do the most work. They separate you from the background without stealing the frame.

Works well Use carefully Usually avoid
Navy, charcoal, slate Black — can flatten on dark backgrounds Pure white — blows out, pulls the eye
Olive, forest, deep teal Bright red — strong, but dominant Neon and highlighter tones
Burgundy, rust, deep plum Light gray — fine, but low contrast Shiny fabrics: satin, sequins
Warm neutrals — camel, oatmeal Cream — better than true white Large logos and slogans

Two practical notes from the studio.

Black on a dark background can merge your shoulders into the backdrop and leave a floating head. If you love black, tell me before we shoot and I’ll light a background that gives you separation.

And pure white is the most common thing I have to work around. It’s the brightest thing in the frame, so the eye goes there first — which is exactly backwards.

What should men wear for headshots?

A well-fitting jacket over a solid shirt is still the most versatile option, because you can shoot with it on and off and end up with two different looks in one session.

  • A jacket in navy, charcoal, or a subtle textured weave
  • A solid shirt underneath — light blue, or a soft mid-tone. Cream and ecru beat true white
  • Ties are optional now in most industries. If you’re in law, finance, or executive search, bring one and we’ll shoot both
  • Watch the collar. A soft collar that has lost its shape is the single most common thing I fix in retouching

Fit matters more than price. A $60 jacket that fits your shoulders photographs better than an expensive one that doesn’t.

What should women wear for headshots?

The same principles, with a few more variables.

  • Solid colors in a fabric with some structure — knit, ponte, crepe, a light wool
  • Necklines that frame the face: a simple crew, a V that isn’t too deep, a collar, or a boat neck
  • Sleeves usually work better than sleeveless for a tight headshot crop, but bring both if you’re deciding
  • Jewelry: one piece, not three. Small studs and a simple chain read as polished. Large statement pieces compete with your face
  • If your hair falls forward, a slightly wider neckline gives it somewhere to go

Layers give us options. A shell plus a blazer is effectively two looks, and it costs you nothing.

What should you avoid wearing?

  • Logos and branding. They date the photo, and they’ll date faster than your face does.
  • Busy patterns. Thin stripes, small checks, and herringbone can create a moiré pattern on camera
  • Shiny fabrics. Satin and sequins bounce light straight back at the lens
  • Anything wrinkled. Steam it the night before. I can retouch a lot, but fabric folds are tedious to fix
  • Brand new clothes you haven’t worn. You’ll spend the session adjusting them
  • Sunglasses on your head, lanyards, badges. They pull the eye every time

What should actors wear for headshots?

Different rules. Actor headshots are casting tools, not credibility tools.

You’re not dressing for “professional.” You’re dressing for the roles you actually get called in for. If you book warm, grounded, best-friend types, that’s a henley or a soft knit. If you read as attorney, detective, or executive, that’s structure — a jacket, a crisp collar.

Bring three to five pieces that map to your specific types, in different tones. We’ll build a range that gives your agent options, which is the point of the whole session.

What should a team wear for company headshots?

If you’re the person coordinating team headshots, send one short email and you’ll save yourself an hour on the day. Something like:

“Solid colors, no logos, no white shirts on their own, no busy patterns. Business casual, or whatever you’d wear to meet a client. Bring a second option if you want one.”

That’s it. Don’t mandate a uniform. Then, it looks like a uniform. A loose range of solid mid-tones across a team produces a set that looks intentional without looking staged.

One more thing that matters more than wardrobe: schedule 5–7 minutes per person, not 3. The rushed ones always look rushed.

How many outfits should you bring?

Bring more than you think you need. It costs you nothing and it costs me nothing.

For a 30-minute Express session, we’ll shoot one look, but bring a backup in case something reads badly on camera. For a 90-minute Signature session, bring three or four. For a two-hour Deluxe, bring five.

Hang them, don’t fold them. There’s a rack at the Logan Square studio and I’d rather you use it than fight a wrinkle for the next hour.

What I actually tell people the night before

Pick two things you already feel good in. Steam them. Put them on hangers by the door.

Then stop thinking about it.

I hope to see you soon.

How Much Do Headshots Cost Chicago? | Pricing Guide

If you’ve been looking into headshots, you’ve probably noticed how wide the range is.

You can find someone offering a quick session for $50.
You can find photographers charging several hundred dollars.
And then there are full personal branding sessions that go well beyond that.

At first, it feels inconsistent.

But it isn’t.

It comes down to the difference between getting a photo taken and creating an image that actually represents you.

What You’re Actually Paying For

A camera isn’t what determines the cost of a headshot.

What matters is how well the photographer understands perception.

When I photograph someone, I’m paying attention to details most people don’t notice. The tension in your expression. The way posture affects confidence. The small shifts that move you from approachable to distant, or from unsure to established.

Those things don’t come from taking more photos. They come from experience working with people who don’t naturally feel comfortable in front of a camera.

Why Lower-Cost Headshots Feel Different

Lower-cost sessions are usually designed for speed.

They move quickly, with limited direction and a standard setup for everyone. That can work if you simply need a photo.

But without time to guide you or refine the details, most people default to something slightly guarded. The image may be technically fine, but it lacks presence.

That’s why so many inexpensive headshots feel interchangeable.


They’re not wrong. They just don’t do much for you.

What Changes in a More Intentional Session

When I work with someone, I slow the process down where it matters.

I guide you instead of rushing you. I adjust lighting based on you, not a template. I watch for the moment when you stop thinking about how you look and start settling into yourself.

That’s the point where the image begins to feel natural.

And that’s the image you’ll actually use.

What Headshots Cost and Where I Fit

In Chicago, most professional headshot sessions fall between $300 and $800 or more, depending on the experience and level of direction.

Here’s how I structure my sessions.

Express Headshots — $200

A simple and efficient option when you need something clean and professional.

  • 30-minute session
  • 1 look
  • 1 retouched image

Book an Express Session

Signature Headshots — $350

The most common choice for professionals who want flexibility and variety.

  • 90-minute session
  • 2 to 3 looks
  • 3 retouched images
  • Full downloadable proof gallery

Book a Signature Session

Deluxe Headshots — $550

A more in-depth session with time to create a full range of options.

  • 2-hour session
  • Up to 5 looks
  • 5 retouched images
  • Full downloadable proof gallery

Book a Deluxe Session

Each option is built around a different need, but the goal stays the same.

I want you to walk away with images you can use everywhere with confidence.

Where “Cheap” Can Actually Cost You

Your headshot shows up in more places than you think.

It lives on your website, your company profile, your speaker page, and your email signature. It’s often the first thing people see.

On platforms like LinkedIn, your photo appears before your experience or background.

People won’t analyze it directly, but they will respond to it.

They decide quickly whether you feel credible, approachable, and established.

A strong image supports everything else you’ve built.  A weak one creates hesitation, even if no one says it out loud.

What It’s Like to Work With Me

Most people tell me they don’t feel comfortable in front of a camera.

That’s normal.

Before we shoot, I take time to understand how you plan to use your photos and how you want to come across.

During the session, I guide you through everything. You don’t need to know how to pose or what to do with your expression. I’ll walk you through small adjustments that make a real difference.

We move at a pace that gives you time to settle in. There’s always a point where it clicks and you stop overthinking it.

That’s when we get the right image.

Afterward, I help you choose photos that not only look good, but actually work for where you’re going.

Headshots in Chicago

I work with professionals, actors, and teams across Chicago who want images that feel natural, confident, and aligned with how they actually show up in their work.

If your current photo feels outdated or no longer represents you, it may be time to update it.

FAQs About Actor Headshots in Chicago

Professional headshots in Chicago typically range from $300 to $800 or more, depending on the photographer’s experience, session length, and number of retouched images. My sessions range from $200 to $550, with options designed for quick updates or more in-depth shoots with multiple looks.

Professional headshots cost more because they include direction, lighting tailored to you, and time to create a natural, confident image. Lower-cost sessions are often faster and less personalized, which can result in photos that feel stiff or generic.

It depends on how you plan to use your photos. If you need one simple update, a shorter session may work. If you want multiple looks and flexibility across platforms like LinkedIn or your website, most people benefit from a longer session with more options.

Creative Headshots to Showcase Your Unique Style and Personality

If you’ve ever looked at your LinkedIn photo and thought, “This doesn’t really look like me… or at least the version of me I want people to see,” you’re not alone. More and more professionals are moving away from stiff, traditional headshots and choosing something with personality—creative headshots that feel modern, expressive, and unmistakably you.

Creative headshots aren’t about props or gimmicks. They’re about visual identity. About showing people not just what you look like, but what it’s like to work with you.

As a photographer specializing in Chicago headshots for corporate teams, artists, entrepreneurs, and performers, here’s my take on what makes a creative headshot work—and how to get one that feels authentic, modern, and on-brand.

What Are Creative Headshots?

Creative headshots balance professionalism with personality. They break the old “gray backdrop + forced smile” mold and use:

  • Color (bold, muted, or branded)
  • Interesting but clean backgrounds
  • Modern lighting styles
  • Angles that flatter without feeling staged
  • Expression coaching that actually brings out real personality

The goal is simple: You—but elevated.

Creative headshots give professionals a chance to stand out visually while staying polished. Whether you’re in tech, real estate, consulting, performing arts, or entrepreneurship, the right headshot communicates confidence, clarity, and approachability at first glance.

If you’re in the performing arts, you may also want to check out my dedicated actor headshots sessions.

Why Creative Headshots Matter More Than Ever

In a world where your first “hello” often happens on-screen, your headshot works as a:

  • Brand statement
  • Thumbnail impression
  • Trust builder
  • Visual handshake

And people judge it fast.

A great headshot can make someone stop scrolling. A mediocre one disappears instantly. Creative headshots bridge that gap by letting people connect with you as a real human—not a stock photo version of yourself.

Where Creative Headshots Work Best

Professionals use creative headshots anywhere they need to show up with clarity and originality:

  • LinkedIn profiles
  • Personal websites
  • Team pages
  • Speaking engagements
  • Actor/artist portfolios
  • Podcast artwork
  • Book covers
  • Social media branding
  • Business cards + digital signatures

If your image is part of your brand, your headshot should reflect the same creativity and intention you bring to your work.

How to Bring Personality Into Your Headshots 

Creative doesn’t mean chaotic. Here are the elements that make stylistic headshots work.

1. Color That Supports Your Brand

Bold color backdrops are one of the most impactful trends in modern headshots.

Think:

  • Deep navy for authority
  • Clean white for modern minimalism
  • Charcoal for timeless edge
  • Rust, teal, or muted pastels for creative fields

Color connects instantly—when done right.

2. Real Expressions (Not “Say cheese.”)

A real smile is felt in the eyes.
A confident stare conveys leadership.
A subtle smirk adds character.

I coach every expression in-session so nothing feels forced or “school picture day.”

3. Modern Lighting That Adds Depth

Lighting is how you sculpt mood.

Hard light = bold, high-contrast personality
Soft light = clean, approachable, editorial
Colored gels = creative edge

The lighting style should complement your field and personality, never overshadow it.

4. Wardrobe That Actually Looks Like You

The right outfit is simple:

Wear something that fits well, feels natural, and aligns with how you show up professionally.

Neutral colors work best. Texture beats pattern. Layers add dimension.

If you’re unsure what to bring, I’ve put together a full guide on what to wear for your headshot session to make that part easy.

5. Intentional Backgrounds

From seamless studio color to texture-rich industrial settings, backgrounds set tone without distraction.

Great creative headshots have negative space—your face stays the focus.

Creative Corporate Headshots: Personality Meets Professionalism

Corporate headshots don’t have to be boring. In fact, most modern companies are moving toward headshots that feel more:

  • Human
  • Approachable
  • Team-aligned
  • Brand-forward

Think cohesive lighting and color, but expressions and angles that reflect each employee’s individuality.

Strong brand consistency + real personality = the modern corporate standard.

Whether you need updated looks for your entire team or a few new hires, we can build a plan that fits your brand and your schedule.

Tips for Getting Creative Headshots You’ll Actually Love

Here are a few ways to get the most out of your headshot sessions:

1. Bring a Small Variety of Outfits

Simple changes in outfit can completely transform the vibe of a shot. Think one more formal option and one more relaxed, plus a jacket or layer you can add or remove.

2. Tell Your Photographer the Story You Want Your Images to Tell

Friendly? Confident? Bold? Calm? Energetic?
Your expressions, lighting, and backdrop should all support that.

The more I know about how you use your headshots—and how you want people to feel when they see them—the better I can shape the session.

3. Trust the Process

Great headshots are coached. You don’t need to know what to do with your hands or which side is your “good” side. That’s my job.

I’ll direct posture, angle, expression, and micro-adjustments so you don’t have to think about it.

4. Don’t Force “Creative”

Creative headshots don’t have to mean wild props, elaborate concepts, or costumes. Some of the strongest images are simple, clean, and grounded—just with a little more personality than the standard corporate template.

Gimmicks don’t age well. Authenticity does.

The Real Goal of Creative Headshots

Creative headshots aren’t just about looking good. They’re about looking like yourself—in the best possible light.

If your current headshot feels outdated or like a version of you from a different era, it’s probably time for something new.

A modern, personality-forward headshot is one of the simplest and most powerful upgrades you can make to your professional presence.

Ready for a headshot that actually feels like you?

My Chicago studio specializes in modern, creative headshots for professionals, teams, and creatives.

You show up. I’ll handle the lighting, direction, expression, and everything in between.

Book your session and let’s create a headshot that looks like the person you are now—not the one from five jobs ago.

Creative headshots use modern lighting, color, backgrounds, and expression coaching to show more personality than a standard corporate photo. Instead of a flat backdrop and a forced smile, creative headshots capture who you are—your style, your energy, and your presence—while still looking polished and professional.

Yes. Creative headshots are designed to look modern and expressive without crossing the line into casual or gimmicky. Clean lighting, intentional styling, and strong expressions keep the image professional, while color and composition help you stand out in a crowded feed.

Choose clothes that fit well, reflect your personal style, and match how you show up professionally. Neutral colors and simple textures photograph best, and layers offer easy variety. If you need help picking outfits, here’s my full guide on what to wear for your headshot session.

For companies, creative corporate headshots combine consistent lighting and backgrounds with natural expressions and angles that highlight each person’s personality. The result: a cohesive, modern team page that looks unified but not cookie-cutter. You can learn more about sessions for teams here: corporate headshots.