Outdoor Winter Photos :: What to Wear

What to Wear for Your Outdoor Winter Family Photos :: Andover MA Photographer

Outdoor winter photos are one of those sessions that I never really saw myself doing a ton of. And then 2020 happened and suddenly nothing was what I had ever expected. During the winter of 2020-2021 I had a definite uptick in late fall and winter outdoor photos. Some of these were out of necessity (like my outdoor Santa Claus photos that just weren’t feasible for me to do indoors safely that year). And others were out of comfort, since not everyone was comfortable being inside the studio. But once I did a few, I realized how much I genuinely loved these sessions! They are definitely on my list of things I want to do more of.

Of course, the main concern for clients when planning outdoor winter photos is a common one. What do we wear? It can be a tricky task styling a whole family photo session any time of year. But when it comes to the winter, there are added obstacles. Namely, looking cute while staying warm. Fear not, I have some tips for this!

Layers Are Key for Outdoor Winter Photos

When it comes to dressing for the weather in New England, you really do have to dress for any scenario. While it’s a safe bet that during the winter it will be too cold to be without a jacket for any amount of time. It is possible that there will be days warm enough that the whole family can shed the jacket for one or two photos at least. Which is why layering is so important for outdoor winter photos! Some opt for a higher number of lighter layers. While others prefer bigger, chunky sweaters underneath jackets. You know what is best for you and your family. But it’s important to remember that these outdoor locations don’t always have anywhere to go to warm up. So it’s better to dress extra warm.

Thick, chunky cardigans are great layering pieces. Just make sure they’re not too big to fit under the jacket!
Warm pants are essential–and something that is often overlooked! These velvety, corduroy leggings will be comfy and warm, and also will add a great pop of color and visual interest with the texture!
Another cute, but cozy, legging option for girls.
These ruffle shoulder long sleeve tops are the perfect layering piece–especially for under any dresses that aren’t quite warm enough!
Sweaters are perfect. And this one is a great pop of color which is perfect if it’s warm enough to ditch jackets for a few minutes, or even just to unzip!
Sweater dresses are a great option for moms. A pair of thick tights or leggings, plus boots, and you’re good to go!
This set looks insanely cozy and still cute!
An off the shoulder sweater is a great option to update the classic sweater look.

Cute and Cozy Outerwear is Perfect

Since chances are the temperature won’t be warm enough to spend much time without a coat on, it’s important to plan your outerwear accordingly. These days it’s not hard to find fancier, but still affordable, options for outerwear. Trench coats, peacoats, even puffer coats are all very cute and stylish. And for kids, there are so many truly adorable options. If it’s on the warmer side, fluffy teddy jackets are a super cute look. If it’s going to be a typical frigid New England day, I’d opt for heavier, warmer jackets. And if there is snow on the ground and you’re not opposed: dress the kids in their snow gear! Snowsuits, mittens, winter boots. That way the kids can play in the snow for some super adorable action/candid photos as well.

I love the classic, preppy look of this cozy coat.
Classic houndstooth is such a pretty option!
This teddy jacket is better if the weather is a little bit warmer. And I love the colorblock neutrals!
Another option for if the weather is a little warmer. The green is such a classic color, and the yellows and oranges are bright, vibrant pops of color.
I love a sweater cape! Make sure you layer underneath it to keep your little one warm enough!
I love how happy and fun this coat is. And the styling for the whole outfit is great inspiration if you like color!
Don’t be afraid to go with a bold color for mom, too!
I love the pop of fur on the collar. Plus the styling for this outfit is great–I love the monochromatic purple look under the neutral camel coat.
You can’t go wrong with a classic wool overcoat for dad!
For the dad who hates jackets: a nice puffer vest is a great alternative!

Cold Weather Accessories for Outdoor Family Portraits

There truly are few things as adorable as a pom pom hat. And that goes for ANY age range. Don’t forget to pack plenty of cold weather accessories for the entire family for your outdoor winter portraits. As parents we often spend so much time planning and packing to make sure our kiddos will be warm and comfy and we forget about ourselves. So this is your reminder: gloves, mittens, scarves, and hats for the WHOLE family. You can even use this as a way to match everyone! Keep in mind the weather and any potential snow, slush, or mud when choosing shoe options as well. A pair of boots is more practical than a cute heel.

Classic striped pom pom hats are a great option.
Classic pom pom hats are perfect for kids. I love the pops of color in this one.
For a little fancier option, this pom pom beret is super cute. And the colors will go with so much!
Want something that will keep your kiddos feet warm but still look nice? Go for a Chelsea style boot!
Pom pom hats are a good idea for any age–even moms!
Chunky mittens are cute, and will keep your hands warm even if you have to run after a toddler.
Don’t forget about the cold weather accessories for dad, too! A classic scarf is a great option.

While it’s not technically an accessory, another thing to think about: hair and makeup! I know I always worry about my cheeks and nose getting a little too pink while I’m outside. Makeup can definitely take care of that. And while I always turn to the gurus on YouTube for tips on makeup and hair, there are actual apps that can help. Have you ever heard of the app GlamSquad? I hadn’t until recently (and haven’t personally used it yet) but it seems like such a cool idea! They come TO YOU to do hair, makeup, nails, anything you need to style yourself. Definitely an option for people wanting to do a little extra pampering!

Remember: Comfort is More Important than Style!

The number one thing to remember when it comes to styling ANY child or family portrait session is that comfort is key. Whether that means avoiding scratchy material, or only choosing certain fits or cuts. You know your child best. If your kiddo is going to be okay in a wool turtleneck, then absolutely bring it on! But if your little one only has one snowsuit that they like, and they’ll be cold and miserable in anything else, then have them wear the snowsuit! Trust me when I say it will be absolutely worth it. For one, your kiddo will be much happier during the session. But also it will be such a cute keepsake to have from this chapter of their lives.

I’ve had clients let their toddlers wear princess dresses or costumes that they swore they did not want in photos. And then those end up being their favorites! Any time of year, comfort is most important. But when it comes to being outside in the winter it’s extra important!

This snow suit is super adorable, looks like the kind of thing a kid would love to wear, and will definitely keep everyone warm and happy!
Have smaller kiddos? One piece suits like this are a perfect choice.

Are you looking for outdoor winter family photos? Crabapple Photography is located in Andover MA and serves clients from around the area including Boston, Medford, Reading, Burlington, and beyond. Kate McKenna has been photographing babies, children, and families of all ages since 2009. Contact Kate today to learn more and to book your session.

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    Welcome to Crabapple Photography! I'm Kate and I've been a family portrait photographer since 2009. My specialty is newborns, babies and children. We have fun! My style is clean and whimsical and I am a detail person.

    My studio is located in Andover, MA and I proudly photograph families in the North Shore of MA, Greater Boston and Southern NH areas. I also offer on location outdoor sessions as well.

    Contact me today!

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