I always say COORDINATE, do not match. Meaning pick 2 or 3 colors and everyone wear a variation of them. I love colors and patterns, layers and accessories.
DO wear patterns! I love little boys and men in colorful plaid shirts. Or little girls in polka dots or stripes. I then would have others bring out one of the colors of the plaid or polka dot shirt/dress and wear a plain colored shirt and pair it with a cute scarf, boots or heels (think pops of color).
DO layers! Put a polo shirt under the little guys plaid shirt. Bring a denim jacket to wear over the dress. A cute pea coat with matching heels is just darling. Switching out layers changes up the look and feel of the photos.
DON'T wear logos! It's very distracting in an image. There are some slight exceptions to this...if you prefer a more urban style sometimes graphic tees work (for example a "rockstar" shirt).
DON'T wear something unflattering or uncomfortable. This seems like a given but if you hate how your arms look don't choose a sleeveless shirt. (do a 3/4 length sleeve)
DO go shopping and purchase new clothes or at least some new items. You are investing in a photo session that you would like the images as beautiful as possible. Put some thought into your outfits!
Here's a few examples:
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