Call me stuck in the 80’s (you wouldn’t be the first), but I do love a good pair of ankle boots. To reiterate: a good pair of ankle boots. I think we can all agree that certain pairs are flat-out disasters, while some are simply sublime. Here are a few guidelines–based solely on my opinion–on how to avoid the disasters:

1. Get actual ankle boots, not the imposters. This means that the top should end at or a few inches above your ankle. Calf-length boots should hit you mid-calf. Anything between the two lengths is awkward and best avoided.

2. No heels. This is bold for a reason. Boots are fine with heels. Booties have heels by necessity. Calf-length boots, if done well, can get away with a high heel. Ankle boots simply cannot. In order to keep them looking simple and clean with a new-wave elegance, for the love of all things stylish, get flats.

3. Don’t go super-pointy. I love a nice almond-shaped toe on just about any shoe (sneakers included, if I could find a pair), and that goes doubly so for ankle boots. Still, I think that round could work well here, and possibly square-ish as well, but pointy… weird.

To illustrate my points, here are some that fit into the NO category:

Ugly

Ugly

Cougar-esque

Cougar-esque

Awkward

Awkward

And now for the good ones;

See? Follow the rules and you end up with as many lovely pairs of ankle boots as you will. Here, here, and here.

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