Without a doubt, one of the biggest anxiety producers around family portraits is WHAT DO WE WEAR??!?
Here's a few rules of thumb:
Not all fabrics are created equal. Jersey knit is NOT your friend for a family portrait session. I'm sorry, I love knit too, but it's NOT going to look timeless. Instead you want to focus on fabrics and garments that have lots of texture.
In larger groups, the more texture the better, BUT make sure the color palette is pretty simple. Above is a great example of attention to texture while keeping the colors to a minimum. This lets us focus on the people but also gives the entire image more interest and that coveted 'timeless' feel.
Shoes can make or break this thing, it's so important to pay attention to footwear! Avoid sneakers at nearly all costs, as well as anything with cartoon characters or lights. Make sure to try on the shoes before the actual session, the worst case scenario is they don't fit your kiddo and they cry and refuse to wear them....
Keep your colors palette to about 3-4 major colors, that INCLUDES neutrals. This gives your images a sense of cohesion and intention. Don't be afraid to choose bold and bright colors or patterned garments in your color scheme!!
4. PERSONAL STYLE
As you plan the final set of outfits, make sure each outfit is something you would wear in another situation. Ideally, your outfit would be great for a baby shower, wedding guest or other semi dressy event. You want to look put together and comfortable; not so comfortable it looks like you stopped by the session on your way to beers with the guys!