What you wear sends a strong message about your personality, professionalism and success. The proper wardrobe selection can mean the difference between a head shot that's simply attractive and one that's truly impressive.
Wear clothing that you know looks good on you – it should be freshly cleaned and free of wrinkles. Whether it's a formal or casual image of you, it should say something about your personal style.
If your image is one of a group of people you work with, you may decide what type of clothing you'll all wear. This communicates a look that is consistent when all your images are viewed together, as on a website, and sends a powerful message to clients and prospects.
As an individual being photographed, it's advisable to bring a choice of at least one other item, whether it's a suit jacket, tie, sweater, blouse or shirt. Avoid stark white, if possible and choose softer off-white, beige or grayed-back colors. Solids are better than small prints. Bring different colors; warm, cool, dark, light, so that we have a choice of what looks best.

If you do your makeup yourself, do your makeup how you usually wear it for an average day, or possibly a nice dinner where the steak is $30 but not $75. Do not wear heavy makeup; a close headshots will show clumps of mascara or dark lipstick. Choose light to medium eyeliners, eye shadows, and lipsticks that are only a shade or two darker than your skin tones. This brings your features out in a subtle manner without making it look like you're wearing lots of makeup. Avoid caking on heavy foundation, or wearing shiny eye shadows or lip gloss: too much shine is distracting on camera and looks wet.

Skin blemishes, pimples, and even wrinkles can be retouched. It's not cheating. I promise.

How much is too much? Everyone is different, so it depends on how much make-up you usually wear: you want your head shotss to be easily recognizable as how you generally look in person. For some people, that means wearing your make-up exactly how you usually wear it, for others it's wearing a little more, for others a little less. If you don't wear much makeup every day, don't do your makeup like Kim Kardashian for your photos.

See below for an example of how to do or not do your make-up: you want make-up to merely smooth out your skin and enhance your features- drawing attention to your features as your features, not your features as brightly colored with too much lipstick or eye shadow. Many thanks to make-up artist Jenn Rhoads for bravely having her photos taken at varying stages of make-up for these photos! None of these photos are retouched:

Clothing:
When you wear a tie, be sure you bring a few with small, subtle patterns. Some men have a favorite “power” tie – if it isn't too bold, it might be the one you want. The best colors are cool or warm, depending on your skin tone. Navy blue is a flattering color for most people, and other good neutrals might be burgundy, brown, deep gray or deep green. If you choose to wear a sweater, be sure to avoid busy patterns and bright colors. Some of my clients get a formal and also a casual photo done for their website or social media. If you're having more than one type of photo, you might mix a knit shirt with a sport jacket for a great casual look. Again, darker colors attract less attention, are more slimming and put the emphasis on your face and eyes. For a more formal look, choose a suit or sport jacket, tie and shirt. If possible, please bring at least one color other than white for your shirt. Please make sure that what you choose has the right fit around the neck and shoulders to avoid any fabric pulling, which could be distracting. Remember, you want people to connect with your expression, not with what you're wearing.
Hair:
Don't have your hair cut or colored right before the photo session – wait 3 or 4 days, or even a week for it to look more natural. Remember to bring a brush or comb, or whatever you need to style your hair the way you like.
Grooming:
Be sure you are clean-shaven and your facial hair is carefully groomed. Take a few extra minutes to shave carefully – those little whiskers will often show up. Any facial blemishes will be removed. Have your hair stylist or barber trim your eyebrows. If your photography session is scheduled late in the day, you may need to shave again.

In terms of color, it is important to stay away from patterns on the fabric, because the patterns can detract from your face. So, don't choose a shirt with floral print, checkers, polka dots, stripes, or any other type of pattern on the fabric. These patterns will make the photo too “busy” and they can be very distracting.
Stick with darker colors instead of lighter colors, because the darker or mid-tone colors tend to put more emphasis on your eyes and smile, instead of the clothing. Always avoid lighter colors that are too similar to your skin tone, because they can make you appear washed out.
It is best to wear colors that are contrasting to your skin, so if you have medium or darker colored skin tones, then you should avoid the earthy colors that are very similar to the color of your skin.
You may consider selecting a color that can help to bring out the colors in your eyes. For example, if you have blue eyes, then you may consider a blue or grey shirt. Or, if you have brown or green eyes, then earthy tones can be very complimentary to your eye color.
Don't go too casual - If you are a fitness instructor, of course you can wear yoga pants - if your job doesn't involve stretching and sweating, NO yoga pants. Even if you go to work in jeans and a t-shirt every day, you can dress up that look to a put-together professional level. If you are really struggling to pull your look together, it might be time to consult a professional stylist. Stylists aren't just for celebrities, and their services can be surprisingly affordable. In fact, you might save money by putting together a more versatile wardrobe with key pieces that you can build around (instead of chasing trends or buying things you don't need).
I usually advise my clients to:
Bring more clothing options than you think you'll need - It never hurts to have choices. Having a variety of looks allows you have a professional, business-oriented headshot, as well as something a bit more casual. You might want a specific look for LinkedIn, but something more relaxed would be a better fit for Facebook or a dating website.
Wear color - Even if you live your life in black and grey, consider adding a pop of color. The human eye is naturally drawn to color - and the majority of my headshots clients end up selecting images with at least some color in their wardrobe. Color can brighten your face and make you look more approachable.