Left: Pretty Woman. Right: Hussein Chalayan.

Over-the-knee boots are constantly going in & out of fashion, & have done since the time of pirates. Yarrr! They were daily-wear for pirates, who often turned the cuffs down, as well as crazy adventurers & buccaneers, who wore them as protection while they were riding & often hid things inside them. Like a treasure chest for the leg, to be sure, to be sure, yarrr! YARRR! Women started wearing them in secret too, because they wanted in on the fun, & would hide them under their long skirts.

The style comes & goes, & in the last couple of years, they have drifted back into style again. We’ve noticed them on the likes of Carine Roitfield & Victoria Beckham, & designers, who have the beadiest eyes of all, have not missed this. Now practically every shoe store has a pair in their front window, & we start to think, ‘Hmmm, I wonder how that would look on me’. But just putting them on takes stacks of confidence, & then, you think, as you stare at yourself in the mirror (& everyone in the shop gawps at you), ‘What the hell would I even wear these with, anyway?’.

My darling, I am here to help. Here is my guide to rocking the most fabulous trend of the season.

Questions for the quivery-kneed.

Can I really pull this off?
Remember that the over-the-knee boot is a STATEMENT. What the statement is, exactly, is up to you, but it is probably more along the lines of, “I am a powerful bellatrix & I am not to be trifled with” than “Here is your library card & a photocopied hand-out of the Dewey Decimal System”. Knawmean? This is not a shoe for the shrinking violet. If your legs are your least favourite attribute, or if cannot handle oodles of attention from men on the street (because believe me, you’ll get it), you should not purchase a pair. Stick to your Hush Puppies or whatever. But if you’re up for a challenge, & if you want to throw down the delicious, fetishy gauntlet, then these are for you.

I don’t really think my thighs are my best feature. Should I go for it anyway?
It all depends on how self-conscious you are. If a stranger’s swiftest glance at your gams sends you into a hyperventilating panic, perhaps you should give this one a miss. All is not lost, though — over-the-knee boots look best when worn with black opaque stockings, so it’s not like you’re really showing them off all that much. Super-secret-hint: ribbed stockings (where the lines run vertically up your leg) will give you a slimmed-down, long & lean-looking thigh without the hassle of going to the gym or giving up eating fried chicken sandwiches every second night!

Top: Chloe, Giuseppe Zanotti, Jimmy Choo, Versace, Michael Kors.Bottom: Gucci, Stella McCartney, Kelsi Dagger, Halston, Prada, Juicy Couture.

Okay, I want to go for it. Should I buy a flat boot or one with a heel?
It really depends on what you’re most comfortable in & what you think you’ll get the most wear out of. I feel that a heel is always more flattering, especially when it comes to something like a high boot which can sometimes make even the leggiest lass look a bit… well… stumpy. But if you loathe wearing heels & wobble violently whenever you even think about a pair, flat boots are probably more your speed.

How high should the boot go?
I think a few centimetres over the knee is best. True thigh-high boots don’t give you a lot of room left over, & can look more like waders than sexy boots. But you know your style best. Try on a few different boots to find out what is most flattering for your body.

Should I go for leather or synthetic?
Leather boots are certainly more expensive, but if it’s in your budget (& fits with your morals), leather is the way to go. Why? Synthetic leather doesn’t breathe, it doesn’t sit as well against the skin (it can look kind of wrinkly & naff), & it’s less durable. Sometimes the colour will rub off or it will crack or split. It also looks cheaper, & because this is a look that can go wrong very easily, looking cheap is to be avoided!

This is not to say you cannot go synthetic; of course, you can. Just make sure you buy the best ones you find. It is worth shopping around (though really, this is true for everything).

If you decide to go for leather, here is a note about suede, because there are a lot of very attractive suede over-the-knee boots on the market. As beautiful as it is, & as wonderfully cosy as leather boots are in the winter, you need to be careful wearing suede boots in the rain. The occasional sprinkle of rain won’t ruin them (just be sure to put trees in them & let them dry out when you get home), but if they get soaked, you’ll be a very sad bunny. The dye in suede also runs like MAD when it gets wet, & it stains. You can Scotchgard your suede boots to protect them from the weather but still, use your common sense. While you are wearing them, don’t wash the car, drink too many cocktails beside a swimming pool, run a marathon during a tropical storm, etc.

PVC & patent leather boots should be avoided too, unless you are really, really, really sure you can pull it off. See: Pretty Woman.

Ugh, I tried on a pair & they don’t stay up when I walk around!
If they don’t stay up, don’t buy them! Realise that they may not be the right boots for you & continue with your search. Constantly tugging on the top of them will drive you bonkers, & if this is the case, know that there is no guaranteed way to keep them up. Liberal applications of Hollywood (or double-sided) tape will do the trick for a while, but even this is not a pinky-swear promise. Sometimes it won’t work. If the top of the boot is super-thin, you can attach suspender belt straps to them, but make sure the belt fits or your boots will just drag that down too! You see where I am going with this: ill-fitting over-the-knee boots will just create more problems than they are worth. If something is worth doing, it’s worth doing properly. Don’t half-ass this one.

As well as making sure they stay up, they should also fit your thigh properly. Think snug, but not so tight your thighs go all bulgy like an unfortunate shibari incident. If you’re swimming in them, it will either a) ruin the proportions you’re trying to go for, or b) make you look like a pirate. I know, I know, yarrrrrrrr, the history & all is cool, but is Anne Bonny really your style icon?

Okay, I bought some! Now, what do I wear with these suckers?
The truth is that the first image that comes to mind for pretty much everyone is Julia Roberts in Pretty Woman, & as charming as she was, she is not the woman we’re hoping to emulate. The best way to avoid looking like you are a woman of the night is to go for contrast (otherwise known as not being too obvious) & not show everything off at once. Over-the-knee boots are all about legs, which means your outfit shouldn’t also be geared to showing off your midriff or cleavage. (This is a pretty basic rule of dressing — you don’t show everything at once, unless you are stuck in Las Vegas & have to turn tricks to get home again.)

Remember that when you put an outfit together, your shoes only convey part of the message — so what you wear them with counts.

Think about proportions. Your boots are long & fitted, so go bigger on top. How would it look if you added a slouchy sweater or a big coat cinched in at the waist? What about a long t-shirt or a radically cut a-line skirt? You could wear them over skinny jeans with an enormous scarf & a leather jacket, with an oversized cardigan or a jacket with structured shoulders.

You also don’t have to show the entire boot to make the most of them. If you think of them more as leggings or stockings, that can free you up hugely in terms of what you team with them. You could wear them with a 40’s style dress, a pencil skirt or a huge tulle petticoat to wonderful effect.

One of the easiest ways to make an outfit visually interesting is to play with proportions & put unexpected things together. Big with small, tough with luxe, vintage with new. Mix it up & see what you can come up with.

Here are some more ideas!

Zara.

The styling of these two images is delicious. It’s all about proportions. The look with the leather jacket is total perfection from start to finish. She’s wearing her boots over black skinny jeans & under an oversized white shirt, which is capped off with a short leather jacket. The jacket gives the outfit its shape, while the white shirt prevents it from looking too severe. Bravo.

The picture of the girl in the (faux?) fur jacket, cinched with a belt, & worn with black over-the-knee boots is just too yummy for me to even pontificate over. If I owned all the components of that outfit, you would be hard pressed to get me to wear anything else. Ever.

In my opinion, what saves these three looks from being trashy is that you’re not even really aware that the models are wearing over-the-knee boots. It’s like a fantastic leathery secret. They just look like they’re wearing fabulous stockings or skinny leather trousers. There is no flash of pale or mottled thigh & not a hint of fishnet. They look powerful, sexy & put-together.

The Hussein Chalayan look is from Fall 2006, & is a total winner. You could wear this outfit to work, after-work drinks, or even on a date with a bit of dazzling jewellery. It’s perfectly understated & just a little bit intimidating all at the same time.

I LOVE how Alice Burdeu (Australia’s Next Top Model winner!) looks in McQueen — totally makes me think of a headmistress at a strict-but-sexy (hey, it’s my imagination) Edwardian orphanage. So good. “No, Oliver! You may NOT have some more!”

I can’t say anything about the Givenchy look because I just drowned in my own drool. Sorry.

Flair Italia October 2009.

This is perhaps not a look to emulate, but I had to include it just because it’s quite brilliant. It might be a good one for the bedroom, though.

Carine Roitfeld in Maison Martin Margiela, by Garance Doré.

Carine (Editor-In-Chief of French Vogue) shows how it’s done. The sleek silhouette of the boots perfectly off-sets the size of the coat. Her outfit is so simple but it is completely genius — there are so few parts to it, but it works seamlessly & wonderfully. She could be wearing anything under that coat — a Garfield sweatshirt, a pair of sequinned hot pants, a bikini emblazoned with the American flag — but it doesn’t matter because the few pieces we can see are A++. & seriously, look at those boots. Oh, Margiela, you did us proud.

So, what do you think of the over-the-knee boot? Is it something you think you could see yourself wearing? I am totally mad about them, & have been schlepping from store to store trying to find The Perfect Pair. When I do, I’ll be sure to let you know.