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A ’90s footwear trend is coming back – but this time, it should be easier

Damien Woolnough

How do I wear boots – stylishly – to work?

Knee-high boots on show during February’s Milan Fashion Week.Getty Images

It’s clearer than a supermodel’s skin that this question is coming from a woman. Fashion might be gender-free these days, but my morning commute shows that men have no difficulty wearing boots, whatever their attire.

If you typically wear pantsuits or tattered shorts to work, this is a judgment-free space: follow their lead and polish your R.M. Williams boots or step straight into a pair of Blundstones. On the other hand, if skirts and tights are your office-attire go-tos, you might be gravitating towards a pair of knee-high black boots, which are suddenly rivalling matcha lattes and Raye in the cultural popularity stakes. In this case, a little more effort is required.

The first step is to pick the right pair. When this trend surfaced in the ’90s, I remember consoling a distraught friend with a tray of Cosmopolitans as she struggled to find a style that zipped over her curvy calves; you’re looking for boots that hit comfortably below the knee and fit around the calves without being restrictive. Today, there are plenty of wide-fit styles available, which is a good thing since Cosmopolitans are not back in fashion – yet.

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Pleated, knee-length skirts nod pleasantly to corporate uniforms in greys and charcoal when paired with crisp shirts. A tartan skirt can add a touch of punk or private-school chic, depending on how you spent your teenage years. Wear pants with your boots, by all means, but if you want them to be appreciated, it’s as pointless as wearing sexy underwear in a ski suit.

When you get home, you can swap them for another ’90s staple, Ugg boots. These should never leave the house.

Got a style conundrum? Email damien.woolnough@nine.com.au

Read more from fashion editor Damien Woolnough:

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Damien WoolnoughDamien Woolnough is the fashion editor of The Sydney Morning Herald and The AgeConnect via Facebook.

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