Summer favorites are holding on strong! Jessica looks classic-chic in this check jumpsuit by Sea NY and block heel sandals from by FAR in a matching neutral hue. The longer sleeves make it a great transitional piece for fall, especially with a denim jacket! We're big fans of the pop of blue from this crossbody bag, and this affordable one from Anthropologie converts into an envelope clutch as well.

Naomi Watts does a perfect outfit for late summer with a knee-length skirt and a basic white tee with block heel sandals. But it's time to start adding on the layers! Contrast buttons make this blazer stand out from the crowd, and this Mango blazer is $60 on sale down from $120! When you go neutral with your outfit, a bag is the perfect way to add a pop of color like Naomi did here with a green crossbody. She opted for ladylike accessories too, with a dainty necklace and pear drop earrings.