Avery,
I am in desperate need of fall boots. What’s in this season?

I’ve already made it pretty clear that I’m obsessed with fall fashion, so I think you can guess what my views on boots are. If you can’t guess, I’ll tell you: I love boots. Brown boots, gray boots, tan boots, black boots — you name it, I want it. But I know how overwhelming shoe shopping can be, so I’m going to help you out and narrow it down to three must-have for this autumn.

Option 1: Ankle boots

While I haven’t always been a fan of the ankle boot, it has really proved itself in the past few years as a wardrobe staple. Wearable with dresses, skirts, jeans and shorts, the ankle boot makes any outfit just a tad edgier. I prefer a flat style for everyday wear, but a wedge bootie is a great option if you have to go from day to night with no time to stop home. Just be careful of the potential cankle effect — a boot that is tight around your ankle or hits right at the bone will make even the most luscious legs look like Danny DeVito’s.

Pair with:
 
Dress
Jacket

Option 2: Mid-calf boots

Mid-calf boots are an excellent height for perpetual jeans-wearers. While I’m not a big fan of mid-calf boots with skirts and dresses, mainly because I think it gives the body a weird, fore-shortened look, they look fantastic with jeans. The only exception I’ll make to the skirt rule is if you’re wearing motorcycle boots, in which case you have free-reign to wear those bad boys with anything you choose. But if you’re tamer than that and plan to purchase those trendy, non-edgy combat boots everyone loved last season or you’re more of a simple, classic kind of girl, stick with skinnies or leggings. You’ll thank me when you see a full-length picture of yourself.

Pair with:
 
Sweater
Leggings

Option 3: Knee-high or over-the-knee boots

To be honest, I’m a little over the knee-high boot. Maybe it’s because every “on-trend” girl I see on a daily basis pairs her leather riding boots with leggings, a North Face jacket and a snotty attitude, but I think you can do better than what everyone else is wearing. Opt for an over-the-knee style instead. Sure, it may seem a little “Pretty Woman” at first, but that’s only if you choose a pair made out of black patent pleather, held together my safety pins and paired with a cutout bandage dress. I’d like to think you’re classier than that. Look for over-the-knee boots in soft tan or brown suede and pair them with jeans and a fall sweater, or a mini-dress and thick, thigh-high socks. You certainly won’t look like everyone else in that get-up.

Pair with:
 
Dress
Socks