What to Wear for an Actor Headshot Session: A Chicago Photographer's Guide

By Gretchen Kelley | Gretchen Kelley Photography | Chicago, IL

One of the most common questions I hear from actors before their headshot session is: "What should I wear?"

It's a great question — and an important one. What you wear in your actor headshot directly affects how casting directors perceive you. The right wardrobe choices frame your face, communicate your type, and help you look like a natural fit for the roles you're pursuing. The wrong choices can distract from your expression, confuse your brand, or make an otherwise great photo feel off.

After more than 15 years of shooting actor headshots here in Chicago, I've seen it all — from actors who bring a single wrinkled t-shirt to actors who roll in with two suitcases. The sweet spot is somewhere in between. Here's everything I tell my clients before their session.

Bring More Than You Think You Need

For a four-look session like the ones I offer at my Ravenswood studio, I recommend bringing at least five to seven tops and layering options. You can never have too many choices. We won't use everything, but having options lets us find what looks best in the lighting and against the backdrop we're working with. Some things that look great in your mirror at home might not photograph the way you expect — and vice versa. That's completely normal, and it's exactly why we try things on and test them together before we start shooting.

Choose Colors That Work for You

Color is one of the most impactful wardrobe decisions you'll make for your headshot. Here are some guidelines:

Colors that photograph well: Jewel tones and muted earth tones are your best friends. Think navy, burgundy, olive green, dusty blue, plum, forest green, and warm browns. These colors add richness to the image without pulling attention away from your face.

Colors to use sparingly: Bright white can be overpowering under studio lights and tends to wash out skin tones. If you love white, consider wearing it layered under a jacket or cardigan rather than on its own. Black can work — especially for theatrical headshots — but on very fair skin it can create too much contrast. Neon or very saturated colors like hot pink, bright orange, or chartreuse tend to look overexposed on camera and rarely flatter any skin tone.

A good rule of thumb: Look at what characters wear on the TV shows you'd love to book. That's your starting point.

Think About Your Type — But Don't Wear a Costume

Your headshot wardrobe should hint at the kinds of roles you're targeting without being too literal. A casting director should look at your photo and immediately get a sense of where you fit — are you the approachable next-door neighbor, the sharp corporate executive, the edgy artist, the warm mom? Your clothing helps tell that story.

That said, don't show up in a doctor's coat or a cowboy hat. Casting directors have strong imaginations — they just need a nudge, not a full costume. A leather jacket suggests something different than a cable-knit sweater, and a crisp button-down says something different than a vintage t-shirt. Use clothing as a subtle signal, not a billboard.

Commercial vs. Theatrical Looks - Whats the best for your Actor Headshot Session?

If you're shooting multiple looks (which I always recommend), plan to cover both commercial and theatrical territory.

Commercial headshots call for wardrobe that's friendly, approachable, and relatable. Think of what you'd see in a Target ad or a cereal commercial — clean, cheerful colors, casual layering, and a warm vibe. Pastels, light blues, soft pinks, and warm neutrals work well here.

Theatrical headshots call for something a bit more grounded and dramatic. Darker, muted tones work best — deep navy, charcoal, black, olive, burgundy. The clothing should feel understated so that your expression does the heavy lifting. This is the headshot that says, "I can carry a scene."

Having both styles in your portfolio gives your agent more to work with when submitting you for different types of projects.

Solids Over Patterns (Usually)

As a general rule, solid colors photograph best for headshots. Busy patterns, logos, and graphics pull the eye away from where it should be — your face and expression. Small stripes and subtle textures like knits, denim, or brushed cotton can work nicely and add some visual interest without becoming distracting.

That said, rules are made to be broken. If a bold plaid shirt is core to your type and personality, bring it. We'll test it and see how it reads on camera. Part of what makes a pre-shoot consultation so valuable is that we can talk through these decisions together before the session even starts.

Layers Are Your Secret Weapon

Layers are the easiest way to multiply your looks without packing a whole extra wardrobe. A simple t-shirt becomes a different look when you throw on a denim jacket. A button-down transforms when you add a blazer or roll up the sleeves. Scarves, cardigans, hoodies, and vests all give us more to work with.

Layers also help because headshots are typically shot from the chest up. You don't need to worry about pants or shoes — it's all about what's happening from the shoulders to the top of your head. So bring plenty of tops and outerwear options.

Keep Accessories Simple

Less is more when it comes to jewelry and accessories. A thin necklace, small earrings, or a simple ring are fine — just make sure nothing competes with your face for attention. Avoid chunky statement pieces, dangling earrings that catch the light, or anything that jingles when you move.

If you wear glasses in everyday life, bring them. We can shoot some looks with and without them. If you don't normally wear glasses but think a pair would work for a specific character type, consider grabbing an inexpensive pair with no lenses — it's a surprisingly effective way to shift your look.

What to Avoid

Here's a quick list of things to leave at home:

Logos and brand names. They date your photos and distract from you.

Wrinkled or stained clothing. It sounds obvious, but it happens more than you'd think. Steam or iron everything the night before.

Clothing that doesn't fit well. Too tight pulls and bunches in unflattering ways. Too loose looks sloppy. Your clothes should fit comfortably and look clean on camera.

Sheer or see-through fabrics. They can look unintentional under studio lighting.

All white or all black outfits. Either extreme can create problems with exposure and contrast. Mix it up.

Ask Your Agent (If You Have One)

If you're represented, check in with your agent or manager before your session. They often have specific preferences about what they want to see in your headshots — certain colors, vibes, or character types they're pushing you for. Their input can save you time and make sure your new photos align with your current marketing strategy.

What Happens at Your Session

Every actor headshot session at Gretchen Kelley Photography starts with a pre-shoot consultation. We talk about your type, the roles you're going after, and which looks make sense for your career right now. On the day of your shoot, we'll go through your wardrobe options together, test things in the lighting, and build out your four looks before we start capturing images.

My studio is located at 4001 N Ravenswood Ave in Chicago's Ravenswood neighborhood — just a block from the Irving Park Brown Line stop with free street parking right outside. It's a comfortable, creative space designed to help you relax and bring your best self to the camera.

Ready to Book?

If you're an actor in Chicago looking for headshots that actually help you get in the room, I'd love to work with you. Schedule your session here or email me at gretchen@gretchenkelley.com. And if you're not sure what to bring, don't stress — that's what the consultation is for.

Gretchen Kelley is a Chicago-based headshot photographer with over 15 years of experience working with actors and professionals. Her studio is located in the Ravenswood neighborhood on Chicago's North Side.

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