This is a classic fall technique. However, if you are dying for jackets, make sure to wear something cute underneath incase the weather doesn't approve of your sleeves. I hate when I am smart enough to wear layers, but am too embarrassed by the bottom layer to take my jacket off! Or worse... forget to shave my armpits and am stuck in the jacket all day.
2. Go for jackets that have breathable material
If you live in extra hot weather (aka Alabama), any jacket can become stifling in September. However, this jacket from Target is the perfect compromise. The sleeves are knit and super breathable. The bit of airflow does wonders.
3. Keep your sundress but throw in a short boot
I am not a huge fan of sundresses with high boots, but a short boot can give you the perfect summer/fall in-between.
And for the little ones:
4. Add a jean jacket over a white onesie.
Before it is quite cold enough for jackets, it still makes me nervous leaving Oliver with nothing to protect his chest. This adorable jean vest allows his arms to stay cool while protecting his chest from any cool breezes. Socks and pants would also suffice but wouldn't be nearly as cute!