Fall is such a beautiful time to capture your family, but if the thought of figuring out what everyone should wear is already making your eye twitch, I promise you’re not alone. As a Chicago fall family photographer, I’ve seen how easily the pressure to “look perfect” can take the fun and meaning out of what should be a really special experience.
Let me be the first to say this: you don’t need new clothes, a Pinterest board, or a color-coded family outfit guide to have beautiful, meaningful photos. You just need to wear what feels like you.
Start with What Matters Most: Comfort and Connection
When you’re planning outfits for your fall photos, the very first thing I want you to remember is this: these photos aren’t about looking perfect. They’re about remembering this season of life.
And that includes the Spiderman t-shirt your kid refuses to take off, the fall dress you’ve worn for ten years, or your favorite oversized sweater that feels like a hug. These clothes are part of your story. When you look back at these photos, I want you to feel that moment in time—not just see it.
Reflect the Season, But Don’t Stress About Trends
Yes, certain colors do look stunning in fall light. Rich tones like mustard, deep greens, maroon, rust, and earthy neutrals photograph beautifully and naturally reflect the season. But don’t let trends box you in. You don’t have to stick to burnt orange just because it’s autumn.
The real magic? Textures. Think cozy knits, thick sweaters, corduroy, linen, or soft layers that bring warmth and movement. They photograph so beautifully and add a sense of depth and intimacy to your images.
Let Mom Go First
This is my number one tip every time: let mom pick her outfit first. Not last. Not after making sure everyone else is coordinated. Pick something you feel confident, cozy, and beautiful in. Then let the rest of the family build around that.
For example, if you’re wearing a soft olive-green sweater dress, maybe your partner wears jeans and a warm neutral henley. Your toddler can wear whatever makes sense—just maybe avoid neon pink with burnt orange. 😉
Coordinate Without Matching
Matchy-matchy is out. You want to coordinate, not clone.
Pick 2–3 tones that work together (like denim, cream, and rust), and let everyone show a little of their own personality. It makes your photos feel more relaxed and natural, and it makes sure everyone is comfortable, too.
What Not to Wear
- Super bright colors (especially neon)
- Uncomfortable or stiff fabrics that make you (or your kids) itchy and irritable
- Shoes that don’t match the location (ditch the heels if we’re in a field)
Basically: wear what makes sense for who you are and where we are. These photos are about documenting your real life—not creating a version that fits someone else’s feed.
And yes, for families with younger kids: always bring a backup outfit or at least a spare shirt. Things happen. That’s part of the beauty.
Wear What Tells Your Story
Your clothes tell a story—even when you don’t realize it. The goal isn’t to fit into a mold. It’s to show up as your full, beautiful, messy, real self.
My fall sessions are full of play, tenderness, laughter, connection, and your clothes should allow you to move, snuggle, and be totally yourself. No stiff pants. No itchy dresses. Just you.
Ready to Book Your Chicago Fall Family Session?
If this sounds like your vibe, I’d love to help you preserve your beautifully mundane and wildly meaningful life just as it is right now. Book your fall session here: Book Your Session
Let’s make this season feel like something you’ll want to remember forever.
—Taylor
