Stilettos and Diapers: Fashion || Fall Transition and School Orientation


Fashion || Fall Transition and School Orientation

With school just 1 week away here, I'm starting to get into fall mode. No, I'm not exactly ready for it, but I do like the idea of being able to layer the clothing on with the arrival of baby #3 soon. 

This is my look for school orientation this year. I think it says "I'm casual enough to sit on the floor and help in your class." It also says "please don't make me get messy or do things involving finger paints." Hahaha
Jeans, White Tee, Gingham Shirt
I sure do love a good gingham and this top from J. Jill is a perfect transition piece. It doesn't exactly work with the baby bump now, but will be perfect to wear while nursing. And I love adding the pop of checks to this otherwise basic jeans and tee outfit. 
Gingham, Backpack
Maternity Style, Gingham, Jeans, Booties
Yes, I am carrying my new diaper bag on the regular already! How cute is this backpack from TWELVElittle? It is so great to fit all my stuff, places for the boys drinks on the side and little pockets everywhere. 
TWELVElittle Diaper Bag Backpack

Karen Walker Sunglasses
And my favorite part of any outfit…the shoes! Booties are so versatile and essential for transition to fall. I just got these at Rack Room Shoes and earned my reward! You get $15 gift card every time you spend $200! 
Fall Transition Booties
Gingham Top
White Tee, Gingham, Jeans
Top: Target | Gingham: J. Jill  | Jeans: Old Navy | Backpack: TWELVElittle  | Booties: Rack Room Shoes | Sunnies: Karen Walker via Ditto (Netflix for sunglasses! Use STILETTODIAPERS for a free month!)

Here are some other cute bootie choices I debated about before settling on the Limelight Kendra I'm wearing with this outfit. 

What is your favorite fall transition piece? Do you have booties that you wear year round? 


  1. are just an adorable preggo Molly! Wish I could pull it off that well! Love the diaper bag!! You'd better let me do your adorable babes birth announcements when he comes! :)

  2. i am just so anxious for that baby to come!


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