Rule No. 1; "Wear what you absolutely LOVE; you have to LOVE it!" If you don't feel comfortable in it, it will distract you from your intentions around the photo shoot and you will generally not photograph well, which makes sense doesn't it? The good thing is that for your headshot, you only need to worry about the top half of your body, but a few options providing some choice on the day would be great.
As for colours, there isn't really a hard and fast rule but some shades will definitely work better with your skin tone than others. Again, being comfortable in what you're wearing will also link to the colour of your clothing choice. So if you bring a selection of garments that you really LOVE, it's likely that we'll also have something of a suitable colour also.
If you really want to leave nothing to chance, Dr Google has plenty to say on the subject. That said, in most cases bold solid colors work well on camera and in particular jewel tones can be striking. Classic black and grey usually do the trick for most also but pastels and lighter colors can tend to be overcome in a studio environment. But like everything, there's always the exception to the rule. If you LOVE it, let's shoot it and see.
Most photographers would also suggest that you should stay away from anything too busy. I'm not necessarily in that camp, but again, it's a 'rule of thumb'. If you look and feel fabulous in it, bring it along!
It often doesn't pay to be too seasonal; we want your shots to endure the test of time for a reasonable period. So classic rather than seasonal. Textures and layers also bring a strong element that can work really well.
Lastly, if you don't have it with you we can't shoot it, so if you find yourself questioning whether or not something will work, just bring it along.
Now; this whole process needs to be FUN (Rule No. 2!), so borrow your best friend's jacket that you love or go shopping for a new wardrobe and return what you don't want after the shoot (leave the labels on). Don't stress it though (Rule No. 3!) as we don't want to break Rule No. 2! Just be 'you' and open to guidance in front of the camera and the rest will take care of itself.
One last thing; there's also no need to worry about jewellery; this gives you one less thing to stress about! We want those viewing your photo to focus on you and you face alone, not your bling!
Here's a link to a nice article by Suzanne McKenzie that helps bring all of the above together in a concise and somewhat fun manner.
Ladies; with respect to make-up, unless you're totally comfortable doing it at a level that can withstand the scrutiny of photographic studio lighting, I suggest you have it professionally done, as it can make all the difference. I can arrange a professional make-up artist for you if you wish. Similarly, the same needs to occur with your hair, it needs to be ready to 'rock the camera' so you can be totally comfortable with your appearance and portraying that inner glow that comes from such.
If you're going to do your make-up yourself, here are some helpful tips for creating a great look for headshot photography with the assumption that we're striving for a bright, professional look (as distinct from a moody/darker appearance):
For hair, style it how you normally do and in a manner that aligns with the purpose and use of your headshots (work, social media, club, etc,). By now you know how you look best and like seeing yourself, but importantly, it needs to look like you in your headshot. Similarly, you want to feel great on the day of your shoot and during the session, so aligning your look to achieve that outcome will have a massive impact.
If you're thinking you need a haircut, leave yourself a few days prior to your session to allow it to settle down. The same applies if you colour your hair and roots etc. need a touch-up.
If your hair is long or 'big' (read thick and heavy), consider putting it up for your headshot to help maintain a focus on your face, rather than hair.
It may also pay to call through your usual salon on the way to ease the burden of getting this important component 'just as you like' and having you feel a million bucks, as well as stress free (refer Rule No. 2!).
Mostly men have the good fortune to not have to worry about make-up and from my perspective as it relates to photography, this is ideal. If you do happen to wear a light concealer or moisturiser, that's fine. In fact, if you have a tendency toward dry skin, some moisturiser on the day would be beneficial. The opposite applies for those with oily skin; there are products available that reduce shine and 'hotspots' that occur under studio lighting. In need, I have have a wonderful product that we can use that helps reduce shine dramatically.
Guys; same as the 'laydeez', proper preparation prevents poor performance. Style your hair how you normally would and in a manner that aligns with the purpose and use of your headshots (work, social media, club, branding, etc,). By now you know how you look best and like seeing yourself, but importantly, it needs to look like you in your headshot. Similarly, you want to feel great on the day of your shoot and during the session, so aligning your look to achieve that outcome will have a massive impact.
If you're thinking you need a haircut, leave yourself a few days prior to your session to allow it to settle down. The same applies if you colour your hair and need a touch-up.
If your hair is long or 'big' (read thick and heavy), consider how best to manage it so it doesn't dominate and helps maintain a focus on your face rather than hair. If you use product, feel free to bring it along if you feel like a change-up throughout the shoot.
If you're a daily shaver, please pay close attention to such in preparation for your shoot. Make sure there's no 5 o'clock shadow if you don't want that look in your photographs. If you sport a beard or moustache, attention to trimming and grooming will make an extraordinary difference, especially if we're shooting for a slick and professional look. If not, then simply prepare yourself as you want the world to see you.
If you're going for something more edgy or moody and portrait like, that's okay too. Just make sure you're happy with where your hair is and where it isn't, so we end up with the world seeing you exactly how you would like. If that means you'd like to mix and match, you are welcome to shave during the shoot also.
Lastly, in respect to wardrobe, bring options, especially jackets, shirts and ties. Say a couple of jackets and shirts plus as many ties that you LOVE. I can then assist in the final selection with an eye to what will add rather than take away from your headshot.