This fall is all about classic looks in shades of gray, and I’m totally feeling preppy! So…I got out my pearls and my houndstooth swing coat and started pulling together a demure, old-school look that feels fresh and on trend. The perfect base for this preppy outfit was a super comfortable gray Jessica London Ponte Knit Dress.

The fit and flare shape is so easy to wear and flattering for many figures…while the seaming at the bust and the waist adds some shape to the dress. For some extra flair and dimension, I decided to wear a denim shirt underneath the dress and then set the whole outfit off with a pop of lemon heels.

Classic prep with some modern flair…perfect for fall in Chicago!