Knee High Boots ~ did they really ever go out of style?

Ankle boots have dominated our wardrobes for many years now. When they first came onto the scene in the mid 2000’s, they took some time to get our heads around. What do I wear them with? Can I wear them with my dresses? What’s the right style for me?

I now own a dozen pairs of ankle boots, in many colours, heel types and heights. And I wear them with everything. Fair to say, I jumped on the ankle boot train with gusto.

For years now I’ve shopped almost exclusively for ankle boots with clients. Occasionally a knee high boot would be on the shopping list. But that doesn’t mean knee high boots went out of style, they just stopped being stocked on the store shelves.

Fashion is a funny one like that. Those who determine what’s in and what’s out (designers, celebrities, bloggers, influencers) absolutely influence our shopping habits, but does it really matter? Enter the knee high boot.

Personally, I don’t think they ever went out of style, but we did stop wearing them. They’re classic, stylish, feminine and sexy. Perhaps not as versatile or affordable as an ankle boot (that’s one reason the ankle boot still rules) but nonetheless it’s a good a wardrobe staple that can provide you with lots of styling mileage.

Here are some ways to style the knee high boot and as always my tips on what to BUY NOW!

With A Midi-Dress

I love the 70’s feel of this look. Relaxed, comfortable and a little boho. A knee high boot works really well under a floaty, printed dress. Depending on your height, a tight fitting boot can work just as well as a relaxed boot. If you do have a softer boot that scrunches on the leg and ankle, make sure it has a heel to maintain balance.

BUY NOW! Midas Tan Leather boots reduced to $195

Under a Long Coat (Kate Middleton is quite the fan)

How easy is this outfit! Throw on a great coat, some knee high boots and you’re set! Ok you might need something underneath but when your wardrobe staples are this good, that’s really all you need!

BUY NOW! Edward Meller slouch boot $375

With A Skirt

There are numerous options when it comes to skirts and boots, but again I like the look of a longer skirt over a knee high boot. A skirt length that just meets or covers the top of the boot can look really elegant for both work and play.

If you have flat boots, try a shorter style skirt. Showing off a bit of leg (bare or even under an opaque stocking) will help elongate rather than shorten like Naomi Watts above left.

BUY NOW! Wittner Cognac Block Heel reduced to $260

I also prefer a slightly A-line skirt with knee high boots, rather than a pencil skirt. However if you want to try a pencil skirt for a corporate look, my advice is to keep the boots closely fitted to your legs and wear a heel, as per below.

BUY NOW! Edward Meller classic leather boot $395

Skirt and oversized jumper

BUY NOW! Wittner Snakeskin Boots reduced to $290

Over Skinny Jeans

This was definitely how we all wore knee high boots back in the day, over our jeans. But remember before skinny jeans were ‘in’ and we had to fold our jean cuffs over (and tuck into our socks) to fit into the boots? Or was that just me?

There are two ways you can style the knee high over jeans:

Casually with a flat, almost horse-riding type boot ~ perfect for day to day, casual weekends and running the kids around, as seen on Nicole Kidman and co below.

BUY NOW! Jo Mercer Black leather boots reduced to $199

Bared nubuck boots $389

Dressy/Sexy with a very fitted, high heeled over-the-knee boot. This look is everywhere online (Google, Pinterest, Instagram) thanks to the likes of the Kardashians and Hadids who have championed this trend for a few years now. In fact, when I looked up ‘knee high boots with jeans’ on all these platforms, it was actually hard to find an image WITHOUT a boot over the knee. Interesting however that it’s not a look I see much on the streets (i.e. worn by ‘real’ people)