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It’s almost the first day of autumn and that means Halloween is coming! To combat my sadness at my pool closing I have to jump head first into fall life. The leaves are beginning to turn and the mornings are cooling off. I have a new Boo sweater from Pink Lily (click here for link) that I love. It is currently out of stock, but these outfits can work with any autumn/seasonal sweater. Here is how I’m styling a Halloween sweater three ways.

With Straight Jeans and Short Boots

This is how I wore it out and about this week, with my Kut from the Kloth straight cropped jeans (click here for link) and short western boots. I love Winnie the Pooh and this cute Halloween Pooh bag from Loungefly will be on my shoulder all of October. I would wear this as my mom-on-the-go outfit.

With Skinny Jeans and Heels

A bit of a more business look with a patterned heel (thrifted these ones!). I would wear this to a meeting, like a PTO/PTA one.

With a Denim Skirt and Knee High Western Boots

This one is my favorite, with the sweater front tucked into the skirt, my new favorite cowgirl style boots (click here for link) and a hat (click here for link). Definitely an outfit I would wear to the pumpkin patch or any fun fall gathering.

Longer denim skirts seem to be everywhere this fall! I grabbed mine back in March at Anthropologie and it has been on constant rotation. Which of these outfits is your favorite?