Before your session…
1. Decide on a color palette
Deciding what colors you want to wear is the best place to start. One easy keyword or phrase to search on Pinterest is, “Fall color palette”, or whatever season you are dressing for. This will give you an idea of what colors work best together. My favorites are: grey, white, beige, light pinks, olive green, light blues, mustard/dark yellows, and navy blue (think earth tones).
2. Start with one piece and build around it
If you happen to find your dress first - then build the rest of the outfits around it. That makes the whole process a lot easier to tackle. If you or your husband is wearing stripes, then the other could wear a solid color shirt, dress, etc. Mixing colors, patterns, and/or textures is a great way to help your session feel like you and give it some dimension.
3. Coordinate outfits instead of matching
Having everyone match perfectly tends to look dated, and pictures seem to lose dimension. Choosing neutral colors with different patterns and textures will photograph best. Adding a pop of color is perfectly fine too, but you’ll want to be careful with what colors you choose. Avoid colors that are considered “hot” or “neon”. They leave a color cast on the skin that is really hard to edit out.
4. Consider your location
If your session is taking place in a field of green grass, choosing a solid green dress might not be the best idea. Remember that a lot of one color or a very bright color can reflect and leave a strong color cast on lighter skin tones.
5. Picking accessories
Less is always more. Adding a simple bow or headband is very flattering to young girls. Little boys always look adorable in a bow tie or suspenders. Here are some other accessories to consider: bow ties, bows or headbands, suspenders, knee socks for girls, necklace or bracelet for mom, scarfs, & non-baseball style hats.
6. If you don't love it, it will show
Wear something that you are comfortable in, that fits, and that you love! It will show through in pictures if you are wearing something that you are uncomfortable in.
P.S. Layering is always a good idea! A sweater over your top/dress or a jacket over a mens shirt is a great way to add to an outfit. It also help during the session as something for your hands to hold onto.
By no means are these rules for any session. These are just my suggestions, that in my opinion, photograph well.