A good black bootie can go a LONG way and by good I don't mean pricey. I've come to wear black booties more than I wear flats because they go with almost everything, add a little bit of funk, and 99% of the time they're super comfy. If you're new to the bootie thing, the key is finding a great suede or leather style that hits BELOW the ankle so it doesn't cut you off; it's an overall flattering silhouette. Ideally it has more of a round toe. Once you've mastered that style, it's all about the mid-ankle bootie with a slimming pointed toe: 

{ justfab sweater // j brand jeans - similar at azalea // justfab booties // justfab bag}

I've rounded up my fave black booties under $100 below. Scoop up a pair and I promise you'll be wearing them all season! 

{pursuing black booties under $100}