How to wear the menswear-inspired flat

From penny loafers to brogues, a dandy men’s shoe can look feminine when paired with the right look. Read on for great advice on how to wear it from a pro stylist


Patent Blucher, Zara


Lapilio Oxfords, Aldo

town shoes

Town Brogues, Town Shoes

What to look for: “Shop for this style of shoe in a bold colour or print to make a statement,” says Kelly Millar, a fashion and image consultant from KM Image Consulting in Toronto. “From a leopard print to bright teal hues, find a unique loafer that works for you. This will add a fun and playful edge to your daily image.” Plus a fun colour or print takes it from mannish to girly.

How to wear it: “A classic loafer works beautifully with a dark wash, slim leg denim for those oh-so-chic casual weekend get-togethers,” says Millar. If your shoe is on the brighter side pair it with basics. If it’s on the classic side, feel free to wear it with everything from your cropped trousers to your pleated skirts for an updated schoolgirl look.

Accessorize it: With a pair of brogues, you don’t need to pull on a pair of socks. Let your ankles peek through if you’re wearing them with cropped or rolled up pants. Or, be bold and try on a statement-making pair of socks. For loafers, try them with tights and a skirt or rolled up denim.

Day to night: “An oxford-style loafer looks stunning with any slim leg trouser for a casual day at the office,” says Millar. For nighttime, pair an oxford with a pencil skirt and top and you’re ready to roll.

A little hit of style: Look for a feminine take on this menswear style. Avoid clunky, heavy styles that could pass for a men’s brogue and opt for one with a more pointed toe and a thinner sole.

Menswear-inspired shoes we love (pictured in the player above):
Town brogues, $100, Town Shoes.
Lapilio oxfords, $60, Aldo.
Patent Blucher, $100, Zara.