Winter family sessions can be magical. The quiet stillness of the season, the soft light filtering through bare branches, and the closeness that naturally comes from staying warm together, all of this sets the scene for heartfelt, cozy portraits.
If you’re planning a winter photo session here in Portland, you might be wondering: “What should we wear?” And while winter styling comes with a few unique challenges (hello, unpredictable weather!), it also offers the chance to play with rich textures, beautiful layers, and timeless tones that elevate your images and keep everyone feeling comfortable.
Here are a few of my favorite tips for choosing outfits that feel warm, natural, and winter-ready without sacrificing style or connection.
Table of Contents
- Start With a Warm, Neutral Palette
- Layer Thoughtfully
- Dress for the Weather (but Make It Cute)
- Coordinate, Avoid Matching
- Embrace the Season
- Final Thoughts
1. Start With a Warm, Neutral Palette
In winter, the world around us softens. The greens fade, the skies go pale, and the landscape becomes more minimal. To complement this, I recommend earthy neutrals and deeper tones like cream, camel, charcoal, rust, forest green, dusty rose, or muted navy.
These colors photograph beautifully in overcast light and add warmth without overpowering the natural environment. Avoid overly bright colors or bold patterns, which can feel out of place and distract from the emotion we’re capturing.
2. Layer Thoughtfully
Layers are a must for winter sessions. Not just for warmth, but for the beautiful texture and dimension they add to your images. Think chunky knit sweaters, long cardigans, wool coats, scarves, and beanies in soft, natural materials.
Cozy layers make everything feel more intimate and grounded. And you can take them on or off as we move through the session, giving you a variety of looks without a full outfit change.
3. Dress for the Weather (but Make It Cute)
We’ll likely be shooting outdoors in the chilly air, so choose pieces that are both stylish and functional. Lined tights under dresses, fleece-lined leggings, thermals, or base layers hidden beneath outfits are great for keeping little ones warm.
Bring a blanket for snuggles and in-between moments. It adds both warmth and a beautiful, cozy touch to your photos. And don’t worry if you need to pause to warm up. We’ll take breaks as needed.
4. Coordinate, Avoid Matching
Rather than dressing everyone in the same sweater, aim for a coordinated mix of colors and textures. Maybe you wear a cream knit dress, your partner a warm flannel in muted tones, and your children in layers of beige, olive, or brown.
Start with one outfit you love and build the rest around that. I’m always here to help you pull it all together and you’re welcome to use pieces from my client wardrobe to simplify the process even more.
5. Embrace the Season
Whether we’re documenting the golden glow of a rare sunny day or the softness of a foggy morning, winter sessions have a charm all their own. The slower pace, the cuddles to stay warm, the way kids tuck into their parents for comfort, all of it creates beautifully authentic images.
Leaning into that coziness through your outfits, rather than trying to fight the season, results in photographs that feel real, relaxed, and true to your family in this moment.
Final Thoughts
Your winter family session isn’t about perfection. It’s about connection. The laughter in between chilly gusts of wind, the way your little one’s nose wrinkles up when they giggle, the way your arms instinctively pull your baby in a little closer to stay warm. These are the moments that matter.
If you’re planning a winter family session, I’m here to walk you through every detail, from styling to final artwork. Reach out to get started.
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