People, we can't ignore booties during Boots Week.
If you haven't tried them, do it already. They are a fantastic alternative to pumps or flats when the weather sucks, and can be used when taller boots are just too warm or too much for an outfit.
1. Maximize versatility by choosing a pair you'd consider wearing with dresses and skirts, as well as pants. They are especially leg-lengthening when paired with tights in the same color.
(Sure, she'd look great in a burlap sack, but you get the idea.)
2. If you have skinny legs and ankles, try some with a fairly narrow leg opening or you may look like you are playing dress up in someone else's too-big clothes. Typically, the higher it hits on you leg, the more narrow the opening.
These Dolce Vita booties could work ($195):
Or these Same Edelman versions might be perfect ($160-190) (also come in black and leopard):
3. If you have larger legs and ankles- and even if you have the dreaded cankles!- you CAN wear these. Try some with a wider leg opening and details that draw the eye down, creating the illusion of a longer leg. Otherwise, your leg line will be cut off and you will appear shorter and possibly stumpy. Typically, the lower it hits you on the foot, the wider the opening.
This Ash pair, with black tights, is the perfect choice ($225):
A similar, but less expensive, Nine West version ($109) would also work well (also comes in taupe and black):
Plenty by Tracy Reese pair is $145):
And a simple, but fun, version with a wide ankle opening (Libby Edelman, $99):
It's collegiate, it's juvenile, it's hideous. With or without tights.
5. I still hate the peep-toe bootie in all its forms (click here for the rant), but if you must do it, do us all a favor by wearing them with tights to keep them seasonally appropriate.