I have owned the same black booties for 3 or 4 years. Every autumn, I’m so excited to get them out of my storage boxes. They are easily my most-worn shoes during the colder months. Eventually I will replace them with an ethical leather version, but until I wear them out I will continue to wear them. Today, I want to share how I have styled black booties 3 ways; although, there are many, many ways to style them.
Honestly, any outfit you style with black flats can be switched out with black booties for the autumn and winter. These are old booties from the Dolce Vita line with Target from years ago.

Top: Target // Vest: Stitch Fix (link gets you $25 credit at Stitch Fix!) // Pant: thredUP (link gets you $10 off your first order!) // Boots: Target
This is one of my most-worn outfits during the autumn and winter seasons. I wear this to work or to church. The booties give me just a little bit of height, and the best keeps me warm without being too hot. I actually sold this vest last year, because it was too big for me after I lost weight. I’ve recently purchased a new vest, but it’s actually olive. We’ll see how it fits into my wardrobe!
Shop similar items in this outfit:

Top: Target // Vest & Jeans: Stitch Fix (link gets you $25 credit at Stitch Fix!) // Boots: Target
This next ouftit is similar but it’s not something I would wear to work. Black booties spruce up any casual outfit, like this one that’s perfect for a casual Christmas party. I’ll have to look for a replacement gray vest, because I will definitely miss this outfit!
Shop similar items in this outfit:

Tee: Target // Vest: Jane.com // Pants: Thrifted via thredUP (link gets you $10 off your first order!) // Boots: Target
Last, but certainly not least, this is the most recent outfit I’ve styled with my black booties. This is one of my absolute faves for this time of year. I’ve always been a fan of a nearly all black outfit with a pop of color, and this buffalo check is perfect right now.
Shop similar items in this outfit:
I hope you enjoyed this post about styling black booties 3 ways! How do you style your boots?