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EDIT: How to wear knee high boots

And our edit of the best you can buy right now

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homeroom
May 23, 2026
∙ Paid

You don’t enter a relationship with a knee high boot on a whim.

First of all, there’s the price — a new, quality pair of leather boots is usually a significant outlay. There’s also the space required to house them in your wardrobe.

And then there’s the psychological factor of what a knee high boot does to you. Because, let’s face it, you’re not the same person when you put on a knee high boot. Something magical happens to the neural pathways in our brain that renders us more confident, more adventurous…more of whatever gives Nancy Sinatra that special sauce.

So, before you commit, it’s worth interrogating how and where you’ll wear them to be sure you’re picking the right kind of knee high. Thankfully, there’s never been a better time to dip your toe (!) in, given fashion’s current love for unexpected proportions and silhouettes (see our mood board below).

Winter Boots 26

In this week’s newsletter, we share our favourite knee high boots (almost all from Australian labels and quite a few for under $500, sometimes even under $400) and our tips on how to style them this season — including pro advice from Soph on how to master them with hemlines/pant legs.

Below the paywall this week, you’ll find:

  • Seven excellent pairs of flat knee high boots — riding style — in shades of brown and black

  • Six of our favourite heeled knee high boots, in varying heel heights, patterns and finishes

  • Visual references of how to style your knee high boots (with skirts, shorts, trousers, tights etc)

  • Expert tips from Soph on how to manage hemlines and styling tricks

A reminder that our paid subscribers also get exclusive access to a host of discount codes — we have a few happening until end of May and a few into June/July at ESSĒN, Nelson Made, Friends With Frank, Anna Rossi, Elka Collective, A.Emery and Reliquia. To become a paid subscriber, sign up below.

Flat Knee High Boots (riding boot-esque styles)

A classic that can be utterly confounding to the uninitiated, but which carries the potential for many interesting style combinations for your lower half. The military and equestrian connotations imbue a flat knee high boot with a preppy, upright, hard-nosed energy that feels in direct contrast with our Australian way of life…and that’s the tension to play in, with floaty skirts or sheer stockings, relaxed tailoring, slouchy jeans and knitwear for the cooler months. With any knee high boot, our preference is for a more relaxed fit through the ankle and calf, which gives a more undone feel to what can otherwise be a very unforgiving shoe (plus, it’s more comfortable).

Vogue Australia
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