Jenny’s What to Wear Guide

Share the ♥︎

chicago family photography sessions

This is, hands-down, my #1 most asked question when planning an upcoming family photography session.

“What should we wear?”

Dressing the entire family is a tough job! But I think wardrobe is SO important. There are just some wardrobe decisions that you can make that will yield better image results. What you wear shows your personality, and when you LOOK good, you FEEL good. When you feel good, you’re more comfortable and you take BETTER photos! So it’s completely worth it (IMHO) to take note of your wardrobe details and plan out a few outfits!

I really love being asked for styling help because all through high school, college, and my early years of first moving to Chicago, I’ve always worked in fashion retail. I’ve worked in small high-end boutique stores (Hiiiiiii Bahama Shop + Patricia Timm!), as well as Banana Republic and J.Crew. And I can’t forget to mention that my mom worked as a fashion designer in Seoul + had her own little prom dress/mother of the bride shop back in Virginia Beach for a few years. Let’s just say that it’s realllly hard to pay full price retail…

Styling Tips DO’s

  • DO try and incorporate clothes that aren’t too ‘stiff.’ Fabrics that feel good to the touch are likely really comfortable to wear too- ESPECIALLY for kids!

    • Flowy, chiffon-y materials for moms do wonders for outdoor environments (think of a spontaneous gust of wind letting that fabric trail behind you…), or while you’re moving around with your child.

  • DO layers.

    • In the fall seasons, multiple layers and rolled sleeves are fabulous. I like to do a fair amount of untucking to make dad’s appearance look slightly undone, without looking too sloppy.

    • In the warmer months, you can layer by having each member wear similar colored tones without looking too matchy-matchy by layering TEXTURES. Or simple things like layered dainty gold necklaces, bangles, and/or rings. It’s best to throw a lot on, and edit off a few pieces.

  • DO buy and use children’s clothing that currently FIT for your kid(s).

    • As a mother, I get that you want to get a lot of mileage out of every kid’s clothing investment. Especially since they grow out of things so quickly. But clothing sizes that are too big tend to translate as ‘sloppy’.

  • DO coordinate clothing that fits each member’s personality.

    • For instance, for a quiet/shy child: muted tones, while their more outgoing sibling can be dressed in brighter colors (just pretty please avoid neon hues!).

  • DO adapt a look to your needs.

  • DO opt for a timeless look. When in doubt, steer clear of too many trends. The last thing you want is to look at your family portraits 30 years from now and wince of the fashion risks you took.

  • DO tell dads to pay attention to their socks. You never know if they’ll show while kneeling down or sitting. For in-home sessions, you can always default to bare feet to convey a more relaxed, casual vibe.

    • DO have dads empty their jean pockets. They tend to store cell phones, wallets, keys, etc in their pockets- I’m assuming because they don’t tote around a ‘man-purse’?. I like to say that I like to keep their bulge centralized, if ya know what I mean!


I LOVE this look for a mom: comfy, but well put together. It’s nice to find clothes that are appropriate for indoors + outdoors, allow for flexibility and comfort in a variety of terrains and situations, and are kid-appropriate (i.e. nothing cut too low or short). 

More examples coming soon!

I’ve sourced similar chinos to the photo on the left. They’re a nice alternative to a denim jean.



My Master SHOPPING List That Will Make Dreams Come True…






Do you have other favorite stores not listed? please share below!