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§ Field Notes · Chicago

Corporate headshot preparation guide.

A field-tested walkthrough for executives, attorneys, founders, and consultants booking a professional headshot session in Chicago. Wardrobe, grooming, posing, and what to expect on the day.

Published 2026-06-13 · 8 min read

A great corporate headshot looks effortless — calm posture, intentional wardrobe, honest expression. Behind that ease is preparation. This guide collects the advice we give every Chicago client who books a personal-brand or executive session with Sam Visions, in the order it matters.

§ 01

Book the right kind of session.

A LinkedIn refresh and a brand-launch shoot are not the same job. Before booking, decide what the image is for: a single profile photo, a leadership page, a press kit, a speaker bio, or a hiring page that needs a consistent team look. Tell your photographer up front — it shapes lens choice, lighting, crop, and how many looks are worth setting up.

In Chicago, plan three to four weeks of lead time for executive sessions and one In Chicago, plan three to four weeks of lead time for executive sessions and one to two weeks for a single-person refresh. Availability tightens around earnings season and Q4 conference prep.

§ 02

Wardrobe: solids, structure, and one safe risk.

Bring three to five tops on hangers. The strongest headshot wardrobes share three traits: solid colors (or a very subtle pattern), structured shoulders that hold a line on camera, and necklines that frame your jaw instead of competing with it.

  • Default to navy, charcoal, forest, burgundy, ivory, or camel. These read as senior on every background.
  • Avoid tight stripes, small checks, and busy prints — they moiré on sensors and pull focus from your face.
  • Bring one piece that feels slightly bolder than your everyday work outfit. A textured blazer, a louder blouse, a tonal knit. It almost always becomes the favorite frame.
  • Iron or steam everything the night before. Wrinkles read as twice as deep under professional light.

If your brand color is part of your identity (a firm color, a startup palette), bring an accessory in that color — a tie, scarf, pocket square, earrings — rather than a full garment. It anchors the photo without dating it.

§ 03

Grooming, skin, and sleep.

Most "I hate how I look in photos" is fixable upstream of the camera. The night before:

  • Hydrate. Skip alcohol and excess salt — both show under the eyes within twelve hours.
  • Sleep seven hours if you can. Rested skin needs less retouching, which keeps the photo looking like you.
  • Get haircuts five to seven days before the shoot, not the day of. Fresh cuts photograph rigid.
  • Shave the morning of (or trim your beard to its cleanest line). Five-o'clock shadow lands hard in close crops.

On makeup: matte over dewy for professional light. Bring blotting papers and a translucent powder for forehead and nose. Lip color should match your wardrobe's temperature — warm tops with warm lips, cool with cool. If a makeup artist is part of your package, send them two reference images of yourself you actually like so they have a direction, not a guess.

Glasses wearers: ask your optician about loaner frames with the lenses popped out, or shoot with anti-reflective coating. Professional strobes catch every reflection an uncoated lens will give them.

§ 04

Posing without feeling posed.

The pose that flatters almost everyone: shoulders angled about fifteen degrees off the camera, chin pushed slightly forward and down (not up), weight on the back foot. It feels strange. It looks intentional.

  • Soften your hands. Tense hands tense the jaw. We'll usually park them — pocket, hip, lapel — so they're not in frame fighting you.
  • Breathe out on the count of three. Most great expressions live on the exhale.
  • If your default smile feels forced, try a closed-mouth half-smile and a real laugh — we'll cut between the two for variety.
  • Bring a song. Music on set drops shoulders faster than any direction we can give.

§ 05

The day of the session.

Arrive fifteen minutes early. Eat something light. Bring the wardrobe on hangers in a garment bag, plus a lint roller and the makeup you'd touch up with at lunch. If we're shooting in your office, give us thirty minutes to scout window light and clear a backdrop wall.

Expect to shoot for forty-five minutes to two hours depending on the package. We'll shoot tethered so you can review frames between looks instead of trusting the photographer's "trust me, it's good." Star your favorites as we go — final retouch selections move faster when you've already pointed at the ones you love.

§ 06

After the shoot: selection and delivery.

You'll receive a private web gallery within five to seven business days. Retouching on selected frames takes another three to five. Standard retouching cleans skin blemishes, stray hairs, and wardrobe lint without changing your face. Anything beyond that — color grades, background swaps, additional crops — is worth asking for explicitly so the editor knows your taste before they start.

When you publish, use the largest file your platform allows. LinkedIn compresses aggressively; uploading at 800×800 or larger keeps the eyes sharp.

§ 07

Ready to book?

Sam Visions shoots executive headshots, personal-brand portraits, and team sessions across Chicago and the suburbs — on-location or at your office. See recent portrait work, or start a project below and tell us what the headshot is for.