What to Wear for Fall Family Photos in Naperville and Chicago

Gone are the days of the matching khaki pants and white shirts on the beach. I say that in almost every planning session when people ask me what to wear and it always gets a laugh, but I mean it. Nobody dresses like that in real life… all matching, and your family photos should look like your family, not a catalog from 2003.

So here is how I actually walk my families through outfits, the same way I do it in our planning sessions.

Start with the end in mind

Before we talk about a single piece of clothing, I ask where these photos are going. On your wall? In an album? The answer changes everything.

If we are creating a piece for your wall, I want you thinking about how you decorate. What colors already live in that room? We pull those colors into the outfits so the finished artwork belongs in your home instead of fighting with it. And if you think your space might change, black and white images are a beautiful way to handle that. They go with everything, forever.

If we are building an album, I worry less about matching your house. Albums are about storytelling, so the outfits just need to feel like you.

Mom picks her outfit first

I joke about this, but I truly mean it. Find your outfit first. Find the thing you feel amazing in, and then everybody else follows suit. Most of the dads I photograph are perfectly happy to wear whatever gets laid out on the bed, and the kids honestly could wear a burlap sack and still look cute. You are the one who needs to feel incredible in these pictures, so you go first.

Coordinate, don't match

The goal is a family that looks like it belongs together, not a family in uniform. Pick two or three colors that work together and spread them across the group. Different textures, different pieces, same palette.

Fall colors, indoors and out

If we are shooting outdoors in fall color, I lean toward jewel tones. Deep greens, burgundy, mustard, navy. They are rich against the leaves without competing with them.

In the studio it flips. Both of my studios are light and bright, so I love soft neutrals there. Creams, warm grays, soft earth tones. For newborns, soft neutrals with a small pop of light pink or light blue.

The thread through all of it: I never want the outfits to be the focus. I want the people and their personalities to be the focus. I once photographed a newborn in a dress that was far too big for her, and all you could see was the dress. You could hardly find the baby in it. That shoot has stuck with me ever since.

What to leave in the closet

Hot pink and neon colors. They cast color onto skin and pull every eye straight to them.

Tiny gingham and very small checks. They go wonky on camera. They remind me of those Magic Eye picture collages from the 90s where you stare until a hidden image pops out. I was never good at those, and I do not want your sweater doing that in a portrait.

Big logos and graphics. Ten years from now you want to see your family, not a brand.

Dress for Midwest weather, then let the studio do the rest

You never know what you are going to get here in October. Sixty degrees, forty degrees, rain, all in the same week. So dress in layers you can add and shed, and here is the part that takes the pressure off: my sessions start in the studio.

Studio 25 Naperville is right in downtown Naperville and Studio 25 Chicago is in Streeterville, so we begin indoors, guaranteed dry and comfortable, and then walk outside when we are ready. In the city the tall buildings mean I can shoot outdoors at any time of day and still get beautiful light. If it rains, we grab umbrellas and make something cute out of it. Rain or shine, your session happens. With everyone's schedules, not having to reschedule matters more than people realize.

Starting in the studio also means you can do two looks if you want. Something a little dressed up for the studio, something casual for outside. Two different feels from one session.

You do not have to figure this out alone

Every one of my clients gets access to Style and Select, where you log in, choose your style and colors, add who is going to be in the pictures, and it helps coordinate everyone's outfits. And if you would rather hand the whole thing off, I work with a stylist in Naperville and can coordinate that too.

Ten Little Bluebirds by Emily Cummings photographs fall family sessions, family portraits, and newborns in Naperville and Chicago, Illinois, on location throughout Chicagoland, and at travel destinations by arrangement. Sessions begin indoors at Studio 25 Naperville or Studio 25 Chicago in Streeterville and continue outdoors, rain or shine, so sessions are never rescheduled for weather. Outfit planning help through Style and Select and a professional stylist are available to every client. Inquiries at www.emilycummingsphotography.com.

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