When customers ask me for advice regarding outfits, the main thing I always tell them is to pick something they like, and that they are comfortable wearing, something that gives them confidence and makes them feel good about themselves.
When taking someone's headshot, facial expression, and body language, are very important, and if you are not comfortable with the clothes you are wearing that will show.
In term of colours I would recommend to go for colours that complement your eyes, and/or skin tone. As an example if you have green eyes I would bring at least one green top with you as that will enhance the colour of your eyes, and really make them pop in the photo. I would also recommend bringing a simple black top, like for instance a black t-shirt, as black is a colour that works well with pretty much everybody, and should everything else fail, that black top could save the day. Said that it's best to bring a variety of different colours with you for the session, and I would normally recommend bringing at least five different outfits with you. That does not mean that we will have to use all five of them, but out of five outfits, we are bound to find one that works, and if we are lucky they might all work.
The reasons why a specific outfit might not work, could be for instance that it does not go well with the background we have picked. I also often have customers who bring with them outfits that look great when you see them in person, but for a head and shoulders headshot, you won't see most of it, and that can drastically change the way the outfit looks.
If you are in the process of picking your outfits for the session, but are not sure about how a specific outfit will look in the headshot, you can take a selfie, or take a photo in front of a mirror, and then crop it tight to see what that would look like once you have cropped it. That can help you picking the outfit for the session, and you can always have a look at how I crop them in my headshots galleries which can be found here:
Actor headshots: https://www.david-photography.com/actor-headshots
Business headshots: https://www.david-photography.com/business-headshots
I wold also be careful with low cut tops and vest like tops, as headshots tend to be cropped quite tightly, and you want to make sure that enough of the outfit is in the shot. Said that, there are ways I can pose you in order to get more of the outfit int he shot.
The other question I always get asked is "what style should I go for?". Well there is no hard and fast answer to that question, but as a rule of thumb, if for instance you work in finance and in your sector people tend to dress quite formal (e.g. suit and tie), you might want to go for a more formal look, whereas if you work in the tech industry, where people tend to dress more casual, you might want to go for a less formal look that gives out more of your personality. If you are unsure or want to use the headshots for both personal, and professional accounts, then the best solution is often to have a variety of looks, and you can then pick your favourites.
For actors it is a bit different, when deciding what outfits to go for, I would focus on what type of roles you normally get cast for, or would like to be cast for, and once again you can try a variety of looks, and then pick your favourites.
Whether to go for a formal or a casual look, is eventually up to you, there is no right or wrong answer, and the fact that in your profession people might normally tend to dress quite formal/casual, does not mean that you have to go the same way.
Once you have picked your outfits, and especially if you have to travel by public transport, I would recommend, if possible, to wear your favourite outfit on your way to the shoot, and to try and fold away the other outfits in a way that does not crease them, as creases really show in the photos, and can make the outfits unusable.
I hope this will help you in picking your outfits for your headshot session, and do feel free to get in touch should you have any questions.