Calendars are filling up fast with the holidays approaching and while shopping may be the main thing on your mind, don’t forget to plan what to wear to all of the holiday festivities! From holiday parties to baking cookies with the family, there’s SO much to do and to help make outfit planning (and packing if you’re traveling like me) easy, I’ve pulled together four holiday looks that will have you covered from head to toe for a variety of occasions.

 Cozy Look:
GoldToe Socks // Cashmere Sweatpants // Slippers // Cardigan // Tank Top

 Dressy Look:
GoldToe Socks // Skinny Black Pants // Over the Knee Boots
// Cashmere Sweater // Statement Necklace // Clutch // Red Lipstick

Outdoorsy Look:
GoldToe Socks // Rainboots // Skinny Jeans
// Fleece // Puffer Vest // Baseball Hat

Casual Look:
GoldToe Socks // Ankle Boots // Boyfriend Jeans
// Sweatshirt // Leather Tote // Earrings 

What are some of your favorite things to wear during the holidays? Anyone have any fun outfits planned (or in mind)?

 This post was sponsored by Redbook Magazine & GoldToe socks but all opinions are 100% honest and my own. Thank you for supporting the brands that help make Pretty & Fun possible – authenticity is important to us and we truly only partner with brands that are a good fit for our blog and audience.