It’s family photography season around Fairfield County! Family photographers like me often work morning, noon, and night every fall because it’s one of the most popular seasons for family portrait sessions! Many families choose photoshoots in September/October not only due to the abundance of colors on display but also because pictures are ready when holiday card season begins.
I’ve been a professional family photographer for many years, and I have a good feel for what looks great in photoshoots. I also have found, through both personal and professional experience, what doesn’t work.
Note: All of the examples in this post are of what TO wear! These clients did a fantastic job of styling.

In this guide, I’ll take a straightforward approach to what not to wear for your fall family pictures.
What Not to Wear: Clothes Mom Doesn’t Feel Good In
Moms, choose your outfit FIRST. Find something you love the look of – on your own body.
If you’re self-conscious about a specific area of your body, find outfits that flatter the parts you love best while minimizing the areas you’re not thrilled with. In other words, if you don’t love your upper arms, wear sleeves with a fun neckline or flatter your waist with a pretty belt. If you’re sensitive about your midsection (like me!), choose flattering layers like a long cardigan over a maxi dress or a well-fitted blazer over dark pants and a shell.
Wear clothes you can move in! You’ll want to be able to bend, hug, and walk around with your family, so if you wear something that you have to tug back into place every time you shift positions, it’ll be nothing but trouble.
Maybe you’re like me and not naturally gifted in choosing fashionable outfits. There are lots of ways to move forward. I love going to my local boutique in Ridgefield, CT, Audrey Road, where I can walk in and explain what I’m shopping for that day. The employees, without fail, walk all over the store and find pieces for me to try on – many of them items I never would have considered. I’ve also had great success walking into Evereve, which has locations around the country, and ordering boxes from StitchFix. Department stores like Nordstrom also have free styling services you can use.
If that’s not your vibe, I recommend pursuing Instagram, Pinterest, Google, and even your friends’ family pictures for ideas and inspiration. But here’s the kicker: look for people whose bodies are somewhat akin to your own and see what looks work for them. If you’re a thin, petite woman, finding outfits that look amazing on a 5ft 8in woman with curves isn’t going to translate perfectly to your body type. Look around the Internet for styles you like, and then mimic those.
Also, check with your photographer! They may have styling suggestions, Pinterest pages, or other resources to help.

What Not to Wear: Summer Clothes on Cold Days
If that’s what you want to wear, that’s your choice. DO NOT DO THIS TO YOUR KIDS. From experience, I will tell you that very little kills a child’s enthusiasm for a photoshoot like being too cold.
You may have the cutest, sweetest sundress you are dying for your daughter to wear. But if that dress isn’t warm enough, and your photoshoot lands on a cold day, do NOT show up with her in just that dress and a pair of adorable sandals. You are setting up your entire photoshoot for failure.
Instead, embrace layers. If you want that sundress incorporated, grab warm tights, a long-sleeved shirt to go under it, and a cute denim jacket/cardigan sweater for over the top with boots or booties for her feet. The whole session will go better 10 out of 10 times. For more tips on warm-weather clothes, keep reading!

What Not to Wear: Ski Coats & Fleeces
These items do not photograph well. Instead, if it’s cold, consider these options: Wool coats, chunky sweaters, plaid scarves, layers, flannel, ear muffs, pom-pom hats, and knit mittens.
Consider dressing kids in long johns or tight-fitting pajamas as a base layer, with a cute outfit over it. Remember, too, that the ground outdoors can be wet, muddy, and chilly on fall days. Leather boots and shoes are ideal for this!

What Not to Wear: Matching Outfits
Gone are the days of everyone wearing jeans and white tee shirts. Instead, aim for a coordinated but not overly matching look. Coordinating colors and styles can add depth and interest to your photos. For example, if one family member wears a patterned shirt or dress, others can incorporate a similar color through solids, accessories, layers, and textures. This approach allows for outfits that blend well together visually, achieving a cohesive look without being matchy-matchy.
I also don’t recommend matching outfits for kids. If you have kids of the same gender, buying them outfits that match 100% might be tempting. Parents of twins are generally extra tempted to go this route! And still, I recommend mixing it up a bit. It generally works better for pictures.

What Not to Wear: Everyone in Jeans
Mix up the bottoms as well as the tops! If everyone is wearing jeans, it makes the lower half of many pictures pretty ho-hum. Try other options like khaki, corduroy, shirts, dresses, tights, and jumpsuits.

What Not to Wear: The Usual Suspects – Neons, Big Logos, Sports Teams, Too Many Patterns
While neon colors may be fashionable in some settings, they can be distracting in your family photos, especially against the earthy tones of autumn. Neon colors also tend to reflect onto your skin in unflattering ways. Stick to muted, fall-inspired colors like deep burgundy, forest green, or warm mustard yellow. These colors complement the season’s palette and create a harmonious look.
It’s also recommended that families avoid overly large logos and words across shirts (like “GAP” or “Big Brother.”) The same goes for sports jerseys and the like. Perfect for the hallways of middle school, but not ideal for pictures.

Finally, in a group of 3-6 people, one person in a pattern looks great when everyone else wears solids, textures, and neutrals. Lots of competing patterns don’t flow together visually in photoshoots.