The sleek bootie is a must. This one transitions so easily from day to night and keeps your look polished. The Joie Reina bootie is my pick for the best looking bootie on the block. It's simple and minimalistic with the perfect 3 inch heel height. If you aren't looking to spend as much, check out this pair by Dolce Vita.
An everyday boot is worn the most and my favorite are the Splendid Roland Ankle Boots. These are super versatile (the tan color is perfect) and can be worn with anything in your closet. I also love the Sole Society Natasha Boot for a more affordable option.
Riding Boots are necessary. The Madewell Archive Leather Boots are classic and the pull tab detailing is my favorite. Another awesome option are the Sole Society Bria Boots for less than $150.
Last, but never least, the wildcard option. It's always a good idea to have a pair of boots like these in your closet. I love the Steven Buckle Boots and would wear them with boyfriend jeans and an oversized sweater. These are a great complement to any Fall look and the price on these is so good.
Shop my favorite Fall Boots