I am a stay-at-home mom that lives in ballet flats. I am finally ready to buy some heels for date nights, etc. and I was hoping to figure out which should be my top 3 pairs to buy. I would mainly be wearing them with skinny jeans. Colors, style, material—any details you can offer would be greatly appreciated! —Kate

If you're anything like me, you won't wear heels that are painful or prohibit you from moving around freely. So let's start with three pairs of heels that are both stylish and comfortable so you'll be more inclined to actually wear them. Here are the three pairs I'd recommend for fall:

1. A tall heeled boot (AE Tall Buckled Boot, $79.95): Something about a tall boot just exudes style, whether you pair them with skinny jeans and a sweater or tights and a dress. Look for something in dark brown or black leather for the most versatility.



2. Heeled ankle boot (American Eagle for Payless "Paige" Bootie, $39.99): Booties with a slight Western feel are having a huge moment right now thanks to Parisian designer Isabel Marant (so you could think of them as Parisian, too). The low chunky heels, padded insole and flexible outsole makes them supremely comfortable.



3. A flirty black pump (Apt. 9 Bow High Heels, $38.99): Predictable, yes, but a black heel is a closet must-have. And there are so many styles to choose from. This one, with a pointy toe and chic bow, is so right-now and timeless all at once. It also comes in dark red or purple in case you already own basic black and want to go with a rich gem hue instead.

Apt. 9® high heels

What are your top three "must-have" heels?