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How to Make Everyone Smile in Family Pictures


How to Make Everyone Smile in Family Pictures

The biggest challenge when selecting outfits for your family pictures is not coordinating pieces.  The biggest challenge is making sure everyone in the family looks like themselves.  It's easy to pick four outfits with navy and mustard yellow. And Maybe when your children are small it isn't that difficult because your kids' style is really just your style.  But as they grow and get a style of their own you need to be mindful that everyone loves what their wearing and feels great.  Because feeling great in your outfit is the difference between a good family photo and a fantastic family photo.

The O Family was super fun to work with.  They have a tween son and pre-tween daughter who know where they like to shop and have strong opinions on their outfits.  Their son is Abercrombie all the way and their daughter loves to mix prints and stand out.  Add in a preppy dad, Anthropologie loving mom and new baby and you have 5 totally different styles that need to compliment each other.

Their photo session will take place outside in the fall color and they wanted outfits to compliment the changing leaves.what to wear for fall family picturesThe result is a twirly-boho-preppy-outdoorsy look that will make everyone say CHEESE!

If your interested in our virtual styling services, send an email to  Thanks to the O Family for allowing us to open our style files to them!  We can't wait to see your pics!




behind the scenes: Gina Cristine Photography Surprise Session

About a year ago my favorite photographer came up with a wacky idea. "What if we work together and do a Surprise Session?  All the families will do is show up.  We will have a scene set and all of the clothes waiting for them.  What do you think?"

Um, that sounds pretty freaking awesome.  What parent wouldn't want to just show up with their kids and have everything ready to go?

So Gina Cristine Photography announced the Surprise Mini Session and it quickly filled up.

Over the last several months a theme and color scheme were selected by Gina and session stylist Jennifer.  We met over our favorite Starbucks drinks to discuss ideas and make sure the Surprise Session vision was cohesive.

Betsy and I scoured Etsy and our favorite designers, working within our $50 per child budget to get each family a complete outfit for the best value.  We discovered Thread Culture, which everyone should heart on Etsy ASAP, called in our friends at Tom & Drew and filled in the gaps with staples from Crewcuts, Gap Kids and Old Navy with a few 'couture' friendship bracelets thrown in for good measure.

Now I would be lying if I said that I wasn't a little nervous about seven families showing up for a photo session without a clue to what their kids would be wearing.  Thankfully, everyone was thrilled and we can't wait to see the finished images from Gina!  Until then, here is a little behind the scenes peek at the Summer '12 Gina Cristine Surprise Mini Session! {WARNING:  amateaur photos were taken by me on my iPhone ahead!}

Interested in having TLSF style your next shoot?  Send us an email at  Visit for information on Gina and her fab team of photographers!


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Perfect Fit by Clinton Kelly

Everyone is going to want to move to the Chicago area.  I'm telling you.  First we get Wonder! and now Clinton Kelly is bringing his new stylist concept to Orland Square Mall! The first location to open, Perfect Fit by Clinton Kelly is a new spin on custom tailoring.  You walk into the store with your outfits in  need of help and his professional stylists give you the rundown on how to fix the look, pin it and send it to the back to be tailored.  You pick up the garment the same day or the next day and it has the perfect fit.  Here is a video where Kelly describes the concept.


This is great for people who have lost weight or women who have had children and their clothes just don't seem to fit quite right anymore.  Or if you love to find vintage pieces but need a better fit.

I am going to raid my closet for the now ill fitting pre baby clothes and I'll let you know how it goes!

For more information go to

Would you use a service like this?  What do you think?

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family style: the b sisters

The B Sisters are three girls - 1, 4 and almost 6 - with similar features but very different personalities.  For their Fall family photo shoot,  mom Amy wanted coordinating looks that would compliment their outdoor photo shoot in the woods.

1.. 2., 3.

4., 5., 6., 7.

8., 9., 10, 11.

Amy had already purchased the denim skirt for Isabel and we were easily able to incorporated that into the looks with a chunky sweater, knit hat and sherpa boots.  Big sister Olivia will have a floral print corduroy dress with a frilly headband and fringe moccasins.  Anna, the baby of the family, gets a plum colored corduroy dress with coordinating knit scarf, patterned tights and mary janes.

The three looks are balanced and coordinated yet each sister's outfit stands alone.  The B Sisters are ready to rock their shoot!

What do you think?  Do you need styling services for your next event or photo session?  Contact us at !

Oh, and by the way, did you see that new little badge on the top left side?  The Little Style File has been nominated for a Best Blog Award from Parent's Magazine!  We would love it if you would take a quick second and give us a vote.  THANK YOU!



family style: first birthday pictures

Maren is turning one and her family is commemorating the event with first birthday pictures with their favorite photographer.  Maren needs two looks for her pictures and her parents need one.  The first look is cozy and comfortable with a sweater dress, adorable knit ear flap hat, tights and moccasins.  

first birthday pictures1., 2., 3., 4.  (alternate boot)

Look number two goes a little more with Maren's vintage, sophisticated style.  Pink is her signature color and this muted tone will take Maren from her birthday photos through the holidays.  Paired with silver Mary Janes and tulle hair bows, it's a picture perfect look.

first birthday pictures

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For the parents, dark denim on the bottom with creams and browns will compliment both of Maren's looks.  Because when you're the parents of the one year old doing the photo shoot, there is no time to change!

what to wear family photos1., 2., 3., 4., 5., 6., 7., 8.

Thanks to Maren and her parents for letting us style their first birthday pictures!

If you have an event coming up and need styling services, send us an email at!