Letter to the Editor: Little Black Booties

Dear Nattiest Natalie I know:

Now that temperatures are dropping my flats and heels no longer do a good job of keeping my feet warm, I realize I need to get a few pairs of boots. But, I'm a little lost, what height works best? How should they fit on the calf? And what color would I get the most use out of?

From Vegan & Fabulous in North Carolina

Hey V&F!

First, let me tell you, one of my very best friends had a similar question a few years ago and googled "little black booties". Unfortunately, she didn't get to see shoes. And I'm fairly certain the rest of us have been to scared to try again, for fear of lifelong visual scarring.

I love boots in winter, as you know. And there are tons of options (including Vegan!), so let's sort through them. Here are the four heights of boots and how to wear them.

Ankle aka The Bootie - these are possibly the most versatile of all boots, since they can easily be worn with dresses/skirts or pants (that weird and obvious line of where your high boots come to under your pants is something to be avoided at all costs.) Generally, I've incorporated this into my wardrobe with with darker colors, like plum, black or gray. Leather, suede, pleather, it doesn't matter. Always with a heel (otherwise you run the risk of looking like Peter Pan). I love them all, except for one. There is one ankle boot that raises about two inches, just above you ankle bone. The granny boot. You can tell this boot apart from others, because you put it one and suddenly feel like a schoolmarm. These boots, pretending to be ankle boots are to be worn under pants and ONLY that way. If they are something you like, dress with intention. They can be amazing on some and terrible on most.

Mid-Calf - these guys are rare, mostly for the reason they look like the schizophrenic cousin of the schoolmarm boot. Or a majorette boot. Neither of which are entirely desirable. What is best in mid-calf is the cowboy boot. A great boot to wear with jeans (where did you think "boot cut" got it's name?) or any skirt you want to add an eccentric flair to. I think every closet should have a pair of. Cowboy boots, if not for the versatility also, the flair they add to any outfit is so fun.

Knee High - the classic go-go boot. Even though no one calls them by that name anymore. I bought my first pair at 14 in Venice Beach, Ca (weird, I know) and have owned at least one pair ever since. The key to a good knee high boot is the calf. They should fit well, obviously. Not so tight it looks like your leg is baking out of the boot, but not so loose they look like you could fit a small animal in there with you. Thankfully, a good cobbler can resize your boot calf, and generally for a fairly cheap price. My rule of thumb with boots: if they are flat boots, I usually wear a riding style (which angle up on the side) and I keep the calves well fitted. With heels tall boots, I prefer a stacked wooden heel to a stiletto for stability (as well as a conscious effort to try to dress down my outfit, since I'm always a little over dressed) and a bit of a looser calf. For colors of boots, just about anything goes. I recommend a heeled black and a flat brown or tan for starters (with the thought of wearing black & darker colors at night & lighter and less severe colors in the day). These work over jeans and with dresses. You'll find they go with so much, once you get a pair or two.

Over The Knee - hands down, the most risky boot. This height is not for everyone. Obviously, what comes to mind, when you think of an over the knee boot, is Pretty Woman. Personally when I go out, I don't want someone to wonder if I'm there with a group or there to make some money. With that thought in mind, I have a pair of black leather over the knee boots that are flat. They are convertible, so I can roll the knee down, slouch them, or even have them stand up straight - depending on who I'm with and where we're going. I recommend only wearing pants with these - again, Pretty Woman. And if you're brave enough to get them with a heel, be conscious of where you are.

I hope that helps give you an idea of boots, V&F! If there aren't a lot of good places to pick up boots, I recommend, zappos.com, endless.com, and piperlime.com. You'll be able to find boots in all shapes, sizes, colors, textures, and materials. Happy hunting!!!