Although I will always love a classic tall boot, this season I am embracing the bootie: Short ankle boots – with or without a heel and embellishments – worn with jeans, dresses, skirts and even shorts. I thought buying a pair of booties at the beginning of the fall fashion season would allow me to create more fashion forward and modern looks with my existing wardrobe. And I was right! I chose these Enzo Angiolini Misoa Booties in black suede that have a two-inch stacked heel and some great buckle detail for an added edge. Not only are they comfortable, but they look great with almost any casual outfit I would normally wear a black tall boot, pump or flat with. I wore them with a floral knee-length skirt I bought at a friperie shop in Paris last spring. It made my vintage skirt look more up to date. Once I started wearing my black booties often, I realized a more neutral pair would add even more choices to my fall and winter wardrobe. Since I love buckle detail, I chose these Sam Edelman Lucca Beach Soja Suede Booties also with a two-inch heel. The color is a gorgeous sandy shade that goes with just about anything. I love them with medium to dark wash denim. Here, I wore them with navy, denim skinnies and an Australian Outback style hat in taupe. Depending on the look I am going for, I sometimes like to roll my skinnies up a couple of times. But I do like to tuck jeans into these slouchy Sole Society Natasha Booties. I wear them with an oversized silk shirt like this Equipment top and skinny jeans. It’s an easy casual and comfortable look that doesn’t look sloppy or dated. For a less casual version of the same idea, I wore black skinnies tucked into booties with another silk Equipment blouse and a black wool hat. It’s such a simple way to look stylish and to be comfortable! Another way to wear booties is with a blazer, tee shirt and boyfriend jeans. I would wear this look out to lunch and shopping or to the movies and a casual dinner. For a more dressed-up look, I would change out the destroyed jeans for a dressier pair and add a feminine necklace. Vibrant silky bomber jackets, like the jackets that were so big in the ‘80’s, are back in style. Try a bomber with skinnies and heeled booties for a look that is more 2013 and less 1983. For my dressiest look, I wore my black booties with a silky layered shell and cropped vintage Dior jacket. I would wear this out on a dinner date with husband or out on the town with girlfriends. Or even to a dressy-casual holiday party. I am thrilled I decided to add booties to my fall/winter wardrobe. There are so many outfit possibilities with the addition of these three pairs of footwear I don’t know that I will even want to wear my tall boots this season! Do you wear booties? What style do you like best? Heeled or flat? With embellishments or without? In a neutral shade or something with color?