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Headshot and executive portrait mistakes you don’t want to make


Everybody needs headshots, and most people hate to have them taken, myself included. (Really!)

You need a headshot—or a few—for your company website, for social media, and for promotional distribution. To do it right is easier than you might think, but I see frequent problems that need to be avoided. I’ll break them out, from less to more personal.

(No bad example pix, by the way—I’m not an unkind photographer.)

What not to wear (I loved the TV series!)

Clothing that doesn’t fit, especially clothing that’s too tight. Clothing should fit you as you are now, not how you hope to be when you lose 15 pounds. Too tight is worse than too loose—too loose often can be corrected with a few out-of-sight clothespins. Gaping plackets are a tell-tale. If you have questions, see a good tailor.

Clothing that’s wrinkled, worn or soiled. Seems obvious, no? You’d be surprised! Clothing should be fresh, clean and pressed. In a large corporate headshot session with a wardrobe stylist, the stylist will probably have a steamer on set. In any event, bring what you’re going to wear separately, on hangers. Wrinkles are distracting. Collars and cuffs should have no signs of wear. Bring a couple of options for tops/shirts/jackets.

Except in finance, & sartorially conservative large corporations—you’ll know it if you work for one—the days of dark business suits are going away. Dress as you normally do for your business on a day when you’ll be meeting with clients.

Men, if you’ll be wearing an open collar shirt, your white t-shirt should not show. (And your formerly white t-shirt not only should not show, it should be thrown out.) While I’m on the subject of shirts, some guys, like me, don’t look so great in open spread collars, but look better in button-downs. Get some advice from someone who’s trustworthy, and wear the right style of collar for you.

Bling. Jewelry should be kept to a minimum unless you’re in the hip-hop business, in which case you know what you’re doing. It can be distracting, and if your watch cost more than a new Lexus, in most cases it should be out of sight—you may not want your potential clients to know you have quite that much disposable income.

Now on to the more personal stuff. Don’t stop reading now.


Just out of the shower or haven’t had a shampoo in a week. Casual is fine, and the times are more casual than they used to be, even as recently as last week. But you’re trying to make a positive impression, and your headshot is often the first chance you’ll have for that. So:

Women: Cut & color a week or so before is perfect time. And a blow out the day of the session is a great idea.

Men: A haircut a couple of days prior is a good time to do it.

Unruly facial hair. OK, this part will get touchy, especially further down in the paragraph, but don’t skip over it. Men, if you’ve got a mustache or beard, trim them. Otherwise, get a fresh shave. And while you’re looking in the magnifying mirror, take care of nose hair, ear hair, and eyebrows. (I told you this was going to get personal.) Women who have eyebrows threaded or waxed should do about it a week prior. And since we live in the Western world, where facial hair on women is not a positive attraction for most, if you’re wondering whether you might want to have other facial hair attended to, the answer may well be yes. It’s quite remarkable what the camera will see close up.



No makeup. Think about it: on TV, everybody in front of the camera wears makeup. Men, too, including politicians from all camps. (Not sure about Duck Dynasts.) There’s a reason for this: the lights on the set bring up imperfections in skin and complexions, and can lend a ghostly pallor to faces. And if you live in a northern city, as I do, the pallor will be eerily visible all around you, especially in the winter. On large corporate shoots we try to budget for a makeup artist. They’ll have access to products you don’t, can see what you can’t see in your bathroom mirror, and understand how the camera will interpret your face. And I recommend a professional makeup artist even for individuals—it’s a great investment. If there’s no budget for a makeup artist, then do it yourself, with careful attention to all of your face, not just the front. Even if you don’t often wear makeup, please, please do it for your headshot. You’ll thank me for the advice. And men, at least apply some moisturizer, and start a couple of days in advance, especially in the winter.

Now you’re ready to book a headshot session—if it’s been a year or more you’re overdue for one.

Thanks to Sharon Becker of SB Beauty  for makeup advice (Sharon is my first choice in makeup artists) and to tailor and style customizer Amanda Edmonds of Trend Simple Wardrobing  for tailoring advice (and yes, Amanda is my tailor).