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

How do I wear boots – stylishly – to work?

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.