If it's ease and practicality that you're seeking in an ensemble, consider wearing a grey knit sweater dress. Take an otherwise utilitarian getup down a more elegant path by finishing off with a pair of grey suede ankle boots.
Turtleneck Long Sleeve Cable Knit Black Sweater Dress, $55
How To Style Sweater Dresses - wit & whimsy
Women's Grey Knit Sweater Dress, Grey Suede Ankle Boots, Black Wool Tights
Sloane Ankle Boot Burgundy - Women's Leather Boots
What's New in My Winter Wardrobe
Hermes Steel Blue Suede Kelly Ankle Boots - 36.5 – I MISS YOU VINTAGE
How to Wear a Sweater Dress with Boots & Shoes: from Ankle Boots
How To Wear A Sweater Dress With Ankle Boots: 7 Outfit Ideas
Women's Grey Ankle Boots & Booties
16 best knee-high boots to wear this fall and how to style them