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Headshot prep: what to wear, the night before, the day of

https://wollenburgmedia.com/guides/headshot-prep · Text or call (402) 989-2372

A headshot is twenty minutes in front of the camera and it has to look like you on a good day. Here's how to get ready without overthinking it.

Updated · 6 min read

The one rule

Wear what you'd wear to meet your best customer. Not the interview suit if you never wear a suit. Not the hoodie if you wouldn't take a client meeting in it. The photo is going on LinkedIn, your website, maybe the office wall, and it should look like the person who walks into the room.

If you're between two outfits, bring both. Swapping a top takes two minutes and we can shoot a few frames in each.

Colors, by background

Where we shoot changes what works. At the studio I keep the background plain so you're the only thing in the frame, and at your office the background is whatever wall or window we pick. Solids beat patterns in both cases.

  • Plain studio background: mid-tones and deep colors look best. Navy, charcoal, forest green, burgundy, camel, a soft blue. They separate you from the background and hold their color under studio light. Pure white and pure black both work, but white can flatten and black can merge into a dark backdrop, so pair either with a layer in a real color.
  • Office wall or window: look at the wall first. Against a white or light gray office wall, a darker top gives the photo shape. Against a wood or brick wall, cooler colors like navy and slate keep you from blending into the warm background. If your company has a brand color, wear something that goes with it, not the color itself.
  • Skip: tiny checks and thin stripes (they shimmer on camera), neon, anything with a big logo or words, and shiny fabric. A little texture like a knit or a tweed is fine and often nice.
For teams

Don't make everyone wear the same shirt. Pick a range (say, blues, grays, and white with a jacket optional) and let people choose inside it. The set looks consistent because the light and the crop match, not because the outfits do.

Necklines and collars

A headshot is cropped close, so the collar is doing a lot of the work. A collared shirt, a blazer over a plain top, a crew neck under a jacket, a simple blouse: all good. Things that fight the crop are very deep necklines (they can read as bare shoulders once the photo is cropped tight), turtlenecks that swallow the jaw, and big floppy collars.

If you wear a jacket, button it or leave it open, but decide before we shoot. Check that the shoulders sit right when you stand up straight. A jacket that pulls across the back shows at the collar. Steam everything the night before; a creased collar is the one thing in a headshot that retouching doesn't fix well.

Jewelry and glasses

Small and yours. A watch, a plain chain, small earrings, a ring you always wear. Skip anything that catches light and flashes, and anything big enough to be the first thing someone notices. If you wear the same piece every day, keep it on.

Glasses: bring them and wear them if that's how people know you. I angle you and the light to keep the glare off the lenses in the first place, and whatever is left gets retouched. If you have an anti-glare pair, wear those. Don't switch to contacts for the day if you never wear them; your eyes will look slightly wrong to everyone who knows you.

The night before

Sleep. Eight hours does more for a headshot than any product. Drink water through the day before, not just the morning of. Go easy on alcohol and salt the night before; both show as puffiness around the eyes by morning, and that one is hard to retouch without making you look like someone else.

Steam or iron your outfit and hang it up. Pack the second option. Check the address and the time. If we're shooting at your office, pick the spot now (see the organizer notes below) so nobody is walking the halls with me at nine in the morning.

Hair, the day of

Your everyday hair, done a little more carefully. Not a new style. A haircut a week or more before is good; a haircut the day before is a mistake, because a fresh cut looks like a fresh cut for a few days. Bring a comb or brush and whatever you use to tame flyaways, and give yourself a minute in a mirror before we start. I'll catch the stray hairs I can see, and retouching gets the rest.

Skin, shaving, and makeup

The same advice for everyone: don't try anything new this week. No new product, no treatment, no first-time anything on your face. If you shave, do it the morning of and give it an hour to calm down before we shoot; if you keep a beard, tidy the edges the day before. Moisturize, then blot any shine right before we start.

If you wear makeup, wear what you wear to work, applied a bit more carefully. Matte over shimmer, because shimmer reads as shine under the light. Bring powder and whatever you use for a touch-up. If you don't wear makeup, don't start for this. Every delivered photo is retouched: blemishes, stray hairs, glare on glasses, the usual. Nothing that makes you look airbrushed.

Posture and expression

This is my job, not yours. I'll tell you where to put your shoulders and your chin, and I talk the whole time, so you don't have to hold a face. The best headshots come from the moment right after a laugh, and I get there by making you laugh, not by asking for a smile. Show up, and I handle the rest.

For the team organizer

If you're booking for the office, a few things on your side make the morning go fast. A team is usually done in an hour or two, and each person is only in front of the camera for a few minutes.

  • A list of names. Send it to me before the day, in the order people are free. I check names off as we go and it keeps the files labeled right.
  • A slot for each person. Put them on the calendar so people aren't all waiting at once and nobody is pulled out of a meeting mid-sentence. I stay in one spot; people come to me.
  • A quiet wall or window. A plain wall with a bit of space in front of it, or a big window with even daylight. A conference room usually has both. Tell me what you have and I'll pick, or send a photo of the room.
  • One example, if you have older headshots. Send it ahead and I shoot and edit the new set to sit next to it. New hires later get shot to match too.
  • Tell people the dress range. Forward this guide and name the range. That covers it.

How picking and delivery work

Right after we shoot, you look at the frames with me and pick your favorites. It takes a couple of minutes and you leave knowing which ones you're getting. We set the delivery date then and there, in writing, so it's not a guess. Individual sessions are $125 with 2 retouched images, and extra images are $50 each if you can't choose. Teams are $200–350 flat by head count, quoted up front, every delivered photo retouched. Files come in LinkedIn, website, and print sizes.

The checklist (print this one)

A week out

  • Haircut done, if you're getting one
  • Outfit picked: what you'd wear to meet your best customer
  • Second option picked
  • Nothing new on your skin this week
  • Organizers: names list, a slot per person, and the room sent to me

The night before

  • Both outfits steamed and hung up
  • Water through the day, easy on salt and alcohol
  • Glasses cleaned
  • Address and time saved
  • Full night of sleep

The day of

  • Shave in the morning with an hour to calm down, or beard edges tidied
  • Everyday hair, done carefully; comb packed
  • Makeup as for work, matte, touch-ups packed
  • Arrive dressed, jacket on a hanger until we start
  • Text me if you're running behind

Leave at home

  • Tiny checks and thin stripes
  • Big logos or words
  • Neon and shiny fabric
  • Jewelry that flashes
  • Contacts you never normally wear

Before you ask

Good questions

What should I wear for a headshot?

Whatever you'd wear to meet your best customer. Solid colors read better than patterns on camera. Bring a second option if you can't decide; trying both takes two minutes.

Should I wear my glasses?

If you wear them every day, yes. That's what you look like. Bring them, and I angle you and the light to keep the glare down; whatever glare is left gets retouched.

Should I get a haircut before?

A week or more before, not the day before. A fresh cut needs a few days to settle. If you're close to needing one, a trim a week out is the sweet spot.

How long does it take?

About 20 minutes for an individual. A whole team is usually done in an hour or two at your office, and each person is only in front of the camera for a few minutes.

How many photos do I get?

An individual session is $125 and includes 2 retouched images, your pick. Extra images are $50 each. Team sessions run $200–350 flat depending on head count, every delivered photo retouched.

When do I get the files?

You pick your favorites right after we shoot, and we set the delivery date then and there so it's in writing. If you need them by a specific day, say so when you book and I'll tell you straight whether that works.

Can you match the headshots our team already has?

Yes. Send one example and I shoot and edit the new ones to sit next to it: same crop, same light, same background feel. New hires later get shot to match too.

Questions?

Text me.

If something here doesn't fit your situation, ask. You'll hear back from me the same day.