The Grown-Up Guide to Wearing Loafers and a Skirt

As much as I have a soft spot for a look Vogue shopping writer Augustine Hammond once described as “sulky-rich-girl-in-detention”, I understand that others would rather not resemble an extra in St Trinian’s. Loafers, with their academic associations, can easily fall into this category, particularly when paired with a sensible skirt. But as this season’s street style demonstrates, a few styling tweaks can take the combination well beyond the room. Below, we take a look at how to style a skirt and loafers without conjuring up the distant sound of the school bell.

Tartan Skirt and Leather Jacket

Swap the blazer for a leather jacket, preferably an oversized bomber with a bit of wear and tear. Add an asymmetric skirt to give your loafers a less studious feel.

Matching Monochrome

For a more polished take, pair classic leather loafers with a monochrome outfit like this one – proof that a long, straight skirt and a simple jacket are all you need to elevate your slip-ons.

Slip Skirt and Long Sleeves

For a more relaxed look, pair your leather loafers with a simple slip skirt and a baggy long-sleeved T-shirt.

Pencil Skirt and Knitwear

Tap into ladylike style by pairing your loafers with a long leather pencil skirt, your favourite knitwear and a do-it-all bag. Keep the colours tonal in rich autumn shades.

Patterns Galore

Add a bit of flair to a simple pair of loafers by embracing clashing patterns up top. Simply style classic brown or black shoes with a statement skirt and an equally eye-catching knit.