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5 Tips for Styling a Fall Family Photography Session

Preparing for a cooler weather family session in the Boston Area

What should I wear?!

It's true—what you choose to wear has a massive influence on the look and feel of a photo session. I'm not here to tell you that you need to buy a new wardrobe, wear something you don't feel comfortable in or spend hours putting together outfit options, but after shooting over 100 sessions, I can tell you that if you spend a bit of time curating a specific look for you and/or your family, you will most likely be happier with the final result.

This shouldn't feel stressful. In-fact, I'm hoping the tips below will help take away so much of the confusion that comes with this part of the process and provide a bit of direction for what to focus on and how to achieve the 'look' you are hoping for.

#1—Wear something that reflects who you are as a family.

We do a lot of moving with kiddos, especially to get them laughing, so make sure you and your family are wearing outfits they are comfortable in (and that are uniquely YOU).  It helps when kiddos are excited about what they are wearing, like this little girl below who was so excited about her new fur vest and the Mama who found the perfectly stretchy yet dressy green romper for our holiday mini sessions last year. Look at what you normally wear and try to build off of that. Borrow items from your friends, rent the runway, but please don’t feel like you need to buy a new wardrobe. If you do decide to go shopping, use it as an excuse to buy that dress you’ve had your eye on for the past few months. Moral of the story…don’t buy your family outfits purely because you think they will photograph well, buy your family outfits if you adore the pieces and will want to wear them again.

Family photograph of mixed race family at the Arnold Arboretum in Jamaica Plain outside of Boston.


Hot Tip: Don’t look at Pinterest or Instagram and try to become what you see in those images. That pinterest worthy mama wearing a rimmed hat and a ton of makeup might feel like a costume to you…think timeless with these images…not OF THE TIME. Poofy sleeves of the 80’s are like the boho hats of the 2020’s…you know what I’m sayin’?

#2—Take your outfits (and shoes) for a test ride.

Put on whatever you are thinking of wearing and give it the ultimate test (in front of a mirror). Jump up and down, reach your hands up high, bend over at the hip, squat, spin, run a little, check out your booty! Give yourself a 360 view because that’s what the camera is going to see!  Watch out for nip-slips, booty cracks, unexpected belly button appearances and anything so tight it was difficult to move!  For kids, Look for shoes that your toddler slips out of, sweaters that ride up and dresses that show a diaper. If wearing a lighter color, hold your hand  beneath a layer of the shirt in bright light, can you see your skin? So will the camera! Light dress shirts are always a culprit. We don’t want to see the outlines of a t-shirt!

Hot Tip: If putting your little one in a dress, always pair with matching short-shorts or bloomers, diaper shots are not so fun. Shoes help pull things together and socks make an appearance so choose accordingly. Avoid overly tight clothing. Loose and flowy is generally better! : ) 

A long flowing dress is a wonderful way to create movement and play with light.

A long sleeved dress works well for both standing and seated poses.

#3—Coordinate Colors and textures.

Unless you are already a pro at styling your family, I would suggest starting from a neutral base and building from there. Neutrals (off whites, beiges, grays) and earth tones (browns, mustard yellows, deep greens, blues, rusty reds) are best at complimenting skin tones, especially on little ones. Choose one earth tone in addition to your neutral and dress the rest of the family in the same tones with variation. Use texture and patterns in the same color tones to create variety while also staying within the same color family.  Avoid bright, vibrant tones (like bright pink), as they can be harsh on skin tones (unless you're really going for a statement piece which I'll always embrace).

Neutral Color Inspiration

Some personal favorite fall combo's, rusty orange and mustard yellow.


Hot tip: Avoid pure white, tiny dots or stripes and super busy patterns. Mix colors between tops and bottoms and NEVER dress anyone in the same exact colored top or bottom to avoid too much repetition in group photos. 


This little family did a great job of mixing both colors and textures to create a fun palette that fit their personality! Even the pup was on brand.

#4—Prepare for cold weather

Fall in New England is a different experience every day! We can have a Monday in the 70's followed by a Tuesday in the 40's. We can't predict what the weather will be for the day of your session so be prepared for anything! Have coordinate warm layers ready just in case they need to be thrown on and bring them with you just in case. Gloves and hats are a good idea for littles since being cold definitely makes them less likely to loosen up for photographs.


Curating some cold weather layers ahead of time means you'll be ready just in case it's chilly day-of!

#5—Choose your outfit first

Whoever you are, reading this post, choose your outfit first and base the rest of the family around you! Having a foundation to work from makes the rest of the decision making much easier.

Some General Guidance

For the ladies

We will be in many different positions—standing, kneeling, sitting—so wear something that flatters these differentiations. I suggest a long flowy dress/skirt or jeans/pants that have a good amount of stretch! Layers are wonderful as well and help give that cool-season look.

Coordinating colors between patterns and solids help visually tie the family together.

A long skirt pair swell with a tucked in shirt, throw on a sweater for cooler weather!

A long, flowing, neutral dress is always a good option if a baby bump is making an appearance.


For the guys

Avoid tucked in or transparent dress shirts. Tucking can be awkward when you are throwing a kid around or doing a lot of bending/twisting. Thin dress shirts can sometime show undershirt lines in photos so be aware of the fabric choice. A good trick is to hold your hand under the fabric in daytime light, if you can see your hand clearly, then you can see an undershirt!

A  linen shirt with the arms rolled is a great, casual look.

Take a tip from this dad and wear a favorite jacket. There is no need to get formal for a session. Decide on the vibe you're going for and then fully embrace it!

A chunky, neutral sweater adds texture and coziness to a fall session.

Always make sure dress shirts are left untucked so that there is room for movement and play with the littles.

For the littles

Comfort is king with little ones, especially between 1-3 years old when anything restricting or itchy ruins their day. I always suggest trying the outfit (including shoes) on your little several days before the session just to make sure they don't decide it's the enemy. Ask them to jump up and down and raise their hands, watch out for shirts and sweaters that ride up constantly. A onesie underneath is super helpful in avoiding the exposed belly! Pick them up in the mirror and see how the outfit looks while you're holding them, this helps you get an idea of what I'll see in the camera since we spend a lot of time close and cuddled! If choosing a romper for a kiddo under one, make sure to double check that the buttons/snaps stay put with a full diaper and moving around. Popped buttons and snaps happen more often than you think!


Sweater dresses with a pop of pattern are a great way to keep the kiddos warm while also adding some personality!

Patterned swaddles and blankets help add some texture and movement to sessions with young babies.

Well planned layers are a great way to ensure your little one is looking adorable and is Also comfortable!

Accessories and fun shoes are a good way to add some fun to a kiddos outfit.

Hot tip: Never force a little one to wear an accessory that they don't want. This includes shoes. Make sure you try things on them before the day of the session to see how they react. If you never put a headband on your toddler, they may be very against wearing one all of the sudden. Some kids need time to get used to wearing new shoes as well, give them a few days to break them in to avoid melt downs!

Day of Suggestions

In advance of your session, please remove all items from your pockets (ahem, I'm talking to you guys) as well as your wrists. Hair-ties can leave indentations which are visible in closeup shots so make sure you take them off at least a few hours before your session time. It’s up to you if you want to leave a smartwatch on. I recommend taking them off because it might be the equivalient of holding a rotary phone in 20 years and I’m hoping you look back at these images for generations to come : )

Still feeling stuck? Ask for help! Send photos of ideas or even ask me to coordinate for you! I'm happy to take some time to make sure you are comforable and feeling confident for your session. Just shoot an email to alice@alicephoto.co!

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