What do I wear to my fall family session? | New Canaan Connecticut Lifestyle Family Session | Kendra Conroy Photography | Fairfield County Connecticut Family Photographer


You must be so excited that your family session is coming up right? You might be questioning what to wear and where you shop for outfits for yourself though and I am here to help!


Here are my tips & recommendations:

What should we wear?

Always start with your outfit mom and then work everyone’s outfits around yours! Dresses and skirts look most stunning because they really flatter every female body, especially on camera!

Long, full-length, flowy dresses and skirts look amazing on camera because they bring extra movement to the photos. Especially in nature, like a field, forest, or in front of a barn. Consider softer fabrics that allow for beautiful movement in the images.

When considering the length of your dresses or skirts, it’s also a good idea to factor in whether or not there will be little ones in your photos. If you have smaller children, I’ll likely have you sitting or crouching on the ground to interact up-close with them. Cute, shorter cocktail-length dresses photograph beautifully, but if you have little ones in your photos, a floor-length dress or skirt, or perhaps a cute midi-skirt, will make moving around with your kids much easier, and look perfect on camera, too.

If you’re an expecting mother, we always recommend floor-length gowns or maxi dresses. These dresses create the best silhouettes to flatter your figure and really highlight your bump.

If you choose to wear jeans or pants I just recommend getting a fit that you really love and feel great in. If you choose to wear something more casual on the bottom, then think about dressing it up on top. A beautiful flowy top or lace accent can make your outfit feel special for this occasion.

What colors should we wear?

-When choosing colors for your outfits, I recommend selecting softer, lighter tones and more muted shades. By avoiding ultra-bright, bold colors, it will help bring all the attention to your faces and let the eye focus on the way you feel about each other. The camera loves lighter tones of neutrals (cream, ivory & white) shades of soft pink and muted blues, mixed with sophisticated light neutrals like heather gray, creams, leather brown, and white. That softer color palette fits beautifully into almost all natural outdoor environments.

Where do we shop? For women’s outfits, It can be so overwhelming to pick out a dress as there are so many options to choose from online and very limited options in person.

  • Maxwell-They have so many neutral options

  • Vici-Such cute options and the shipping is fast!

  • Baltic born-Love love this store! They have great quality options and shipping is pretty fast!

  • Lulus- They have fast shipping and their site is very easy to shop for a specific color /style.

  • Piper & Scoot-Another favorite!

  • Livyandkateclothing-

Dress option

  • -Nothing fits but- Super cute options both for maternity and non-maternity!

Tip #1 COMPLEMENT & COORDINATE BUT DON’T GET TOO MATCHY! Find a color palette that you love and choose outfits that complement each other without looking too matchy-matchy. We want everyone to look unique and portray their individual style. Stay away from ‘blue jeans and a white t-shirt’ for everyone or outfits that don’t allow personality.

Tip #2 Layers-The chilly temps are here be sure the little ones are dressed warm and are comfortable. For outdoor family sessions during the fall season, it is better to be warm and overprepared than not warm enough. I would suggest picking out a coordinating sweater for your little one and tights to bring with you if the temperatures are chilly.


Try not to have everyone in the exact same outfit or color for top and bottom. It makes the image more visually interesting to break up colors or patterns.

I am always available to chat and help style your family!


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