Be Comfortable: Good pictures will require a certain comfort level from you, the subject. If you are scared of losing your balance in high heels or sweating under that polyester shirt then good pictures are going to be harder to come by. Stick to clothes you like, that build your confidence and are functional and comfortable.
Keep it Simple: Dark, plain fabrics usually work best. Avoid crazy patterns, designs and logos too. Clothing with distinct lines, dots and bright patterns can be troublesome too. Same goes for shiny fabrics. Keep your jewelry choices simple and minimal.
Avoid Short Sleeves and Shorts: Long sleeves and pants are the superior choice. Skin tones can vary a bunch on various legs and arms not to mention the lighter complexion can distract the eye when viewing the pictures.
Ask Before Wearing Whites: Yes, dark solid print clothes are generally better, but rules are made to be broken. Talk with your photographer before the shoot if you are considering a white shirt. It can look awesome in certain kinds of backgrounds and environments.
Props (nothing hokey here): Does your lovebird indulge you with an old-fashioned picnic once in a while? How about a tune on the guitar? Bring along a few items that reveal unique aspects of your relationship.
Classic, timeless styles: Great pictures last a long, long time so be sure your clothing choices will age gracefully. What is the fashionable trend today can easily be tomorrow's parachute pants so stow away the Ed Hardy shirts.
Hats, scarves and accessories for extra cute children's portraits: An oversized ball cap or a football jersey from Mom and Dad's alma mater always works well.