Before I begin, let me just say any woman can get away with wearing knee-high boots, but not all women can wear the same style. Why not? Cos we don’t all have the same leg length or leg shape. If you’re 6’ tall, nearly any pair of boots are going to look fantastic on you. If you’re like me (the 5’4 and under club) you need to be very careful, lest you look like a little girl who wandered into mommy’s closet.

Let’s consider the basics:

The boots should actually fit your calves.

Your legs may be long enough to pull off any pair of boots, but you need to make sure the width of the shaft is appropriate for your legs, too. For example, even though I have curvaceous thighs, I have very slender calves and narrow ankles. This means the average pair of boots with a standard shaft width are too bulky on my legs – and actually makes them look wide and fat. And the big gaping results are not flattering.

So how do I avoid gaping material that makes my legs look twice as bulky?

By wearing boots that are already tightly molded in the shaft, and making sure they have a bit of stretch in the material, so you know you’ll be able to wear them.

My calves are thick and tend to spill over the edge of boots – how do I prevent this?

By doing the exact opposite – buying a pair of non-molded boots, that also have a bit of stretch. And break them in before you go out on the town. Walk, bend down, etc; you want to stretch them out as much as you can so they’ll be comfy.

If paired with a skirt, should I go barelegged?

That depends: If the skirt covers your knees, it doesn’t matter if you wear stockings or not. If your knees are clearly visible, make sure they look good. If you have knobby knees, all you’re going to do is distract from the boots and put all focus on your knees. If you’re wearing a mini skirt, you should wear some kind of stockings (thigh high or full-on nylons) unless your legs are nicely colored. Pasty white thighs are not attractive!

How do I know how long my skirt should be?

That depends on how long your legs are from knee to crotch, and how they’re shaped. My legs do not look good in a skirt that stops an inch or so above the boot. I either need to wear one that comes exactly to the top, or wear one that stops about 3-4 inches above my knee. This is something you have to find out for yourself, buy trying things on. You can’t know without experimenting.

Should I wear them with jeans?

Um, probably not, sorry. If you have long, sexy legs – go for it. If you’re short, this probably won’t look the way you want it to. Short people got no business wearing this style most of the time, it just looks bad on us. If your legs are long enough though, go for it.

Should I get pull-ons, lace up, or zip up?

Zip up, fo’ shizzle. Especially if you went the way of tightly molded. You don’t want to be stretching the material overmuch. Lace ups are pretty hideous usually, so I have to advise against that just on fashion principle. Pull ons will only work if they are bigger than your legs, but realize you will be stretching them somewhat every time you put them on.

What colors look good?

Black, mahogany, chocolate, tan look good – white, red and most other colors look like crap.

What material works best?

Leather and suede. Avoid fake leather unless you’re a PETA person, cos the fake stuff usually looks really, really crappy. And be careful with suede, it can look ratty after awhile. Also, unless you’ve found high quality patent leather, your best bet is something matte.

What about the heel itself?

1. Avoid super chunky heels, these make your feet look bulky.

2. Avoid pin-style stilettos, these make you look like a hooker.

3. Avoid a wooden heel, these look cool but will hurt like hell after awhile.

My favorite brand

I’ve just bought a new pair of Chinese Laundry boots (see photo) and have to say I find them terribly sexy. They were also highly affordable. If you have a favorite boot brand, feel free to mention it in the comments section.

xx Isabella