What I recommend to wear to a portrait session:
Don't let the photo shoot be the first time you try something on, You want to feel comfortable and confident and sometimes new clothing can fit different of lay differently than what you had in mind. It is important that you have tried them and have worn it to make sure it fits and looks the way you want it.
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Make sure you dress for weather and be prepared to be flexible with your wardrobe just in case you have to switch last minute to accommodate the weather.
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The most important part of anyone’s wardrobe is that you let your personality shine through in what they are wearing.
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When choosing your location and your clothing you want to make sure that they complement each other.
Color
Wear solid color.
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Choose muted tones that are a bit subdual.
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Choose 1-3 colors for your group portraits, ones with similar tones and that complement each ther. Then have everyone work with that color palette.
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Choose complementary tones for your top and bottoms.
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Patterns: If you're wearing plaid or stripes when standing next to a wall it can be very distracting.
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If you are taking photos for a card, invitation or announcement and know what your cards will look like try to pick colors of your outfit that will complement your card color.
Size and Type
Fitting clothing (not tight) is very flattering.
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Check jackets and shirts to be sure that the collar won't block the face in any way when you are standing or sitting down.
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You will want to choose a top that has sleeves to the elbows; it will slim down your arms and is more flattering on everyone.
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Long pants for men/ladies or skirts to the knees or longer for the ladies.
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Skinny jeans are flattering with most women, even the curvy ones if you don't like skinny jeans and don't feel comfortable in them, I would recommend a skinny boot cut.
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Timeless clothing always has a place especially with children. These outfits will always stand the test of time.
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Dress your kids in clothing that fits properly. If their clothing is too big and baggy on them, it won't complement them as well.
Foot wear
You will want to choose dark socks and foot wear.
For your children: Stay away from cartoon shoes, flip flops, crocs. I would recommend plain shoes, boots or leather sandals.
Bear feet are always welcomed when appropriate.
Jewelry and Accessories
Keep jewelry simple minimalistic.
Layers can add depth and dimension. In warm weather you can layer a dress with a belt and a necklace. In cooler/cold weather you could layer belt, scarfs, hats, blazers, necklace, cardigans, etc. The best thing about layers is you can add or subtract them according to the weather.
Hair
Do your hair the way you normally do it while wearing those clothing.
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If you need a haircut try to do it 2 weeks before your shoot.
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Hair accessories are great kept simple for all ages.