I get asked that a lot, so I decided that a post on this subject will be a useful addition to my blog.
Comfort: The single most important thing is for you to be comfortable during the photo session. If you are not comfortable in what you are wearing, or in how it fits, it will show in your facial expressions and body language. Some people are comfortable in stilettos, and that's great! But if you are only comfortable in flip-flops, please wear the flip flops!
Matching outfits: when I say 'matching', I don't mean identical. Identical sometimes looks ok, but most of the time, it's an overkill. It is important to have the same level of "dressiness" - if one person is dressed for an upscale wedding reception, and the other one is wearing jeans and t-shirt, the couple will not look like they belong together. It is also good to think about the colors - do all colors in both outfits coordinate to some extent? Are the patterns complementing or confilcting?
Color and texture: I generally recommend wearing solid colors, preferably muted (not too bright/saturated). I advise against stark white or deep shiny black. Bright colors detract atention from the faces, and bright white and deep black do not photograph as well, because they bring a lot of shart contrast to the images. I also advise against patterns or large details and logos on the clothing - they will also detract attention from you. Having said all that, these are my recommendations, not requirements. If you love bright pink Juicy Couture tops, and they express your personality better than a muted dress - go for it!!
Change of clothes: I recommend bringing 2-3 different outfits along for the shoot, or at least 2 tops to change into. It will give some variety to the images. Extra accessories work well for women - some jewelry, a scarf or a shawl - these can instantly change your look without too much work. For men, it is not as easy - but if your woman has a dressy outfit packed, consider bringing a tie - it can quickly dress you up from the waist up for some close up shots (and I'll make sure that your jeans are not in the frame for those shots!)
Some inexpensive clothes: why does this matter? Sometimes, the mood, the weather and the environment set us up for some real fun creative shots: rolling in the grass, wading in the fountain, sitting on the pavement, and so on. It's a real shame if your nice clothes prevent you from having fun and getting those unique images that express your character. So wearing something that you don't mind getting a little wet and a little dirty is often a good idea.
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