This is the question that every single person ponders before their portrait session. Here are a few tips that I think will help with the tedious task of deciding on what or what not to wear.
This can make a difference in clothing choices. For example, I think urban environments tends to go better with more casual clothes such as jeans and fun shirts.
For dressy shots, guys usually look good in khakis and long sleeved shirts, girls in fun dresses and skirts.
Multiple clothing changes are a plus! Bring several outfits, both casual and dressy and switch them up! Sometimes the day of shoot you might have a complete change of heart as to what you want to wear at a certain location. I love dress cloths in country shots!
Texture is everything. Frayed jeans, wooly sweaters, and layers all photograph really well. Consider scarves, hats, jackets, etc. Texture makes skin appear smooth and creamy and makes faces “pop”.
Accessorizing can make a shot. Big and bold is better even if it is not something you are use to. Small accessorizes don’t show up in pictures. Long, dangly earrings and chunky bracelets look awesome in photographs. The camera tends to lose details, so wear a little more makeup than you usually would, concentrating especially on the eyes and lips. Don’t forget about the hair. You may want to consider a visit to the salon and have a professional style your hair (and possibly do your makeup). This will make a big difference in the final images.
Coordinate, don’t match. In other words, when multiple people are photographed together, you don’t want to clash, but you don’t want everyone to look the same. One thing that works well is to pick a palette of 2, 3 or 4 colors and have the group pick outfits within those colors.