What to Wear: Holiday Tree Farm Sessions 2023

We’re all booked and ready to go and now the age old question- what should we wear? Here are a few tips as you prepare for your session.

1. Dress warm and in layers

This is my top tip for outdoor sessions this time of year. If people are cold, especially children, it really comes through in the photos. Think of incorporating jackets, scarves and hats into your images, especially if it will be chilly at the time of your session. We can pop jackets on and off for photos, but being prepared to be photographed in warmer clothes makes us much more versatile and comfortable.

Layering can add depth and texture to your holiday session. Consider wearing sweaters, cardigans, scarves, or shawls. Layers not only keep you warm but also provide opportunities for creative styling and posing. Textures add some visual interest to your photos. Examples include chunky knits, tweed, denim, and wool.

A very cozy family! Boston Public Garden, December 2021

2. Start with the most difficult person to style

There is usually one person in the family who has either strong personal tastes- or may be a little more difficult to style for whatever reason. For example, a few years ago, that was me! I started by planning my own outfit and then we built the rest of the family’s outfits from there. This year, with a teenager, they have very strong opinions, so we started there.

3. Coordinate, don’t match

While coordinating outfits is essential, avoid dressing everyone in identical outfits. Instead, go for a harmonious color scheme or theme that complements each other's attire. This allows individual personalities to shine through and adds visual interest to your photos. If you are having a hard time choosing colors, choose ONE patterned piece- this could be a shirt, dress, scarf, etc. Pull the colors for all other pieces from this pattern. 

Opt for classic, timeless pieces that won't look outdated in a few years. 

4. Consider the background 

The tree farm is very green! Colors that look great here are jewel tones and warm neutrals. Pops of color are great to break it up. Try to avoid green, and lots of dark colors. Classic red can be used to be festive, but think if it more of an accent rather than a full outfit.

5. Dress for your personality

While embracing the holiday theme is important, don't forget to let your personality shine through. If you have a quirky or unique sense of style, feel free to incorporate that into your outfit to make your photos uniquely "you."

Embrace individuality! Instead of forcing kiddos to conform, embrace their individual flair! Less stress and the kids will be happier. For our own family photos, this meant letting my son wear his “comfy pants” as opposed to khakis or jeans.

6. Keep comfort in mind

The key to a successful photoshoot is comfort. Make sure you can move freely in your chosen attire, as your session will involve sitting, standing, and some playful prompts with your kids. 

7. Footwear

After all this planning, don’t forget the footwear! Shoes don’t have to be fancy or expensive, but do consider how your footwear complements your outfit. Heels can be hard at the farm. Think of what looks most natural for the setting - shoes, booties, boots.

8. Be festive but avoid overdoing it

While it's important to embrace the holiday spirit, remember that subtlety can go a long way. Avoid over-the-top outfits that may distract from the people in the photos.

9. Test outfits in advance

Before the big day, try on your chosen outfits and see how they look together. This will help you identify any wardrobe clashes or issues before the photoshoot. If you have any questions at all, throw your outfit choices on your bed, take a photo, and text me! We can talk through options together.

10. Consider hiring an expert

Lisa Ann Schraffa Santin /LASS Wardrobe LLC is a wonderful local stylist, and has helped me plan for our own family photography session! Her packages start at just $75, and she can assist you via zoom and text to keep things easy. To book a free consult, visit https://www.lasswardrobe.com/

Here are my top 5 things to avoid:

  • Multiple patterns

  • Solid black and solid white tops

  • Too many colors/ clashing colors

  • Shirts with lots of graphics, logos, or writing

  • Lots of classic red


    Overall, I’m here for you! Don’t hesitate to email or text with any questions you may have. I’m looking forward to seeing you!

-Tracey