I reached out to a photographer friend, Kim Lowery, for a little guidance and here is what she said:
I love Kim's last piece of advice. It gives me permission to rock an outfit that best captures my personal style at this very moment. So who cares if my strong-shouldered, sequin jacket paired with thigh-high boots makes me wonder what the heck was I thinking in 10 years, I will at least know I was having fun and embracing the moment. To me that is way more interesting than a classical portrait.
Old school answer: Stay away from patterns or stripes. Keep it simple, and try to match or at least coordinate. Avoid whites and other light colors as they compete with light skin tones. Avoid showing very much skin as it can compete with your face which should be the focus of the portrait.
I'll admit, I have given some of that advice in the past, but times have changed. THANK GOD!
Have fun! It's important that your photos reflect you or your family. Don't be afraid to throw on your holiday dress and heels or your tie and blazer. If your session is on a cold day (or even if it's not) wear your winter scarf and gloves. Bring your favorite accessories. Ask your photographer if you have time for one outfit change or at least an accessory change. Try something casual and something formal.
The most important advice I give my clients about their clothing choice is that they need to feel good in what they are wearing. I want them to feel that they look their best and to be comfortable with what they have on.
Take notice of magazines and blogs to find pictures of families or couples who are wearing something you like.
And on one last note, I think it's important for all of us to have classic and timeless pictures of ourselves or our families, but these pictures also represent who you are today or this year. Your pictures will reflect your style during this time of your life, and that is just as important.