Headshots for Men in Naperville and Chicago: What to Wear, What to Expect, and Why You'll Actually Like Them

Men book portrait sessions at a fraction of the rate everyone else does. I've been doing this long enough to know that it isn't because they don't need the photos... it's because nobody has ever told them what happens during one. So here's the whole thing, start to finish, no mystery.

You need better photos than you think you do

The photo on your LinkedIn profile is doing work whether you like it or not. A hiring manager, a potential client, a referral partner, someone deciding whether to take your meeting... they look at it for a few seconds before they read a single word you've written. If it's a cropped wedding photo from 2017, or a selfie in your car, or a group shot with somebody's shoulder still in it, that's the impression.

The same goes for your website, your speaker bio, your team page, your author photo, and the profile of whatever industry association you belong to. One good session covers all of it for the next several years.

What to wear for a men's headshot

Bring more than you think you need. Three to five tops is the right number for a standard session, and here's how to choose them.

Solid colors photograph better than patterns. Mid-tones and darker tones, navy, charcoal, forest, deep rust, black, do more for you than pale colors, because they let your face be the brightest thing in the frame. A white or light shirt works beautifully but usually needs a layer over it.

Fit matters more than brand. A well-fitting shirt from anywhere beats an expensive shirt that's a size off. Check the shoulder seam: it should sit at the edge of your shoulder, not down your arm.

Bring a layer. A blazer, an overshirt, a denim jacket, a good sweater. Layers give us two completely different looks from one setup, jacket on, jacket off, which is the cheapest way to double your gallery.

Iron everything, and bring it on a hanger. This sounds obvious and it is the single most common thing people skip.

Get a haircut a few days before, not the day before. Shave or trim the morning of, however you normally wear it. If you have a beard, tidy the neckline.

Bring the thing you actually do

This is the part nobody expects and it's the part that changes everything.

If you're stiff in photos, it's not because you're bad at photos. It's because standing in front of a camera with your arms at your sides is a genuinely unnatural thing to do and your body knows it. The fix isn't confidence. The fix is having something to do.

So bring the object. The guitar, the tools, the bike, the sketchbook, the espresso setup, the dog, the ball, the thing you'd be holding on a Saturday morning. The moment your hands have a job, your shoulders drop, your jaw unclenches, and you stop performing. I've watched it happen hundreds of times and it works on everyone.

It also makes the photos yours. A guy against a grey backdrop is interchangeable. A guy in an alley with his bike is a specific person with a specific life, and that's what people respond to.

Studio or on location?

Both, and you don't have to choose blind.

My studio is in downtown Naperville, and it's the right call if you need clean, versatile, corporate-friendly images: white or dark backdrops, controlled light, fast.

On location is the right call if you want the photos to feel like your actual world. Downtown Naperville has brick, alleys, and good architecture within a few minutes' walk of the studio. Chicago gives us the Riverwalk, the skyline, high-rise interiors, and industrial texture. And your own office, shop, or workspace is often the best option of all, because it's where the work actually happens.

A lot of sessions do both. We start in the studio for the clean stuff and walk outside for the character.

How long it takes

A focused headshot session runs about an hour and gets you two to three looks. A full branding session runs two to three hours, covers four or more looks and multiple locations, and gives you enough images to carry a website and a year of social posts.

You'll get your gallery back within about two weeks. Retouching is included and it's light by default... I'm not going to hand you back a face you don't recognize. If you want more or less, just say so.

What happens in the first ten minutes

You'll feel awkward. Everyone does. I'm going to talk to you the whole time, tell you exactly where to put your chin and your hands and your weight, and show you the back of the camera early so you can see it's working. Somewhere around the ten-minute mark you'll forget to be self-conscious, and that's when we get the real ones.

You don't have to be photogenic. That's my job.

Frequently asked questions

What should a man wear for a headshot? Wear a well-fitting solid top in a mid-tone or dark color, navy, charcoal, forest green, black, and bring a layer like a blazer or overshirt. Bring three to five options, all ironed and on hangers. Avoid busy patterns, logos, and anything that doesn't fit at the shoulder.

How much do men's headshots cost in Naperville? Session pricing depends on how many looks and locations you need and whether you want a single headshot or a full branding set. Get in touch and I'll send you current pricing along with a recommendation for which option actually fits what you're using the photos for.

How long does a headshot session take? About an hour for a standard headshot session with two to three looks. Two to three hours for a full personal branding session with multiple looks and locations.

Should I smile in my headshot? Yes, and also no... we'll shoot both. You want a warm, approachable frame and a more neutral, serious frame, because different platforms call for different things. Your LinkedIn photo and your speaker bio don't need to be the same picture.

Do you photograph headshots on location or in a studio? Both. The studio is in downtown Naperville. On-location sessions happen anywhere in Naperville, Chicago, and the surrounding suburbs, including at your own office or workspace.

How soon do I get my photos? Roughly two weeks, delivered as a private online gallery with high-resolution downloads and web-sized versions ready to upload.

Let's get you a photo you don't wince at

If the picture representing you right now is a decade old or cropped out of something else, let's fix it. It takes an hour.

Call or text me at 312.600.5151, email emily@emilycummingsphotography.com, or come find me at Studio 25, 25 W. Jefferson Ave, downtown Naperville.

Warmly, Emily