Classic Man-Tailored Shoe Styles For Fall ’16

Taryn Rose Shoes
Taryn Rose mid-heel instep-strap style with patent leather cap toe.
George Chinsee.

Wives and girlfriends raiding their guys’ closet is a familiar fashion tactic. From the quintessential boyfriend shirt to the today’s popular boyfriend jean, women have always felt comfortable in looks with a man’s point of view.

This fall, the comfort footwear market is following suit in styles that borrow tailored details reminiscent of the men’s market from cap toes to kiltie fringe. But, simply because these looks take inspiration from men’s wear, doesn’t mean they’re without feminine charm.

Taryn Rose leads the way with an update to the Mary Jane, adding a bold buckle and patent leather cap toe. Life Stride does its take on the classic, updating it in a neat herringbone fabric and adding a mid heel.

Life Stride Shoes Life Stride mid-heel Mary Jane in herringbone fabric. Alice and Olivia hosiery. George Chinsee.

For a more casual approach to the trend, moccasins rule in versions from The Flexx and Sofft that pick up tassels treatments, also a popular accessory in the handbag market. Rounding out the story are smoking slippers from Tamaris to the iconic penny version by Aerosoles, a his-and-hers look popularized back in the ’50s by Hollywood icon James Dean.

Women's Loafers Loafer styles from Tamaris, Aerosoles, The Flexx and Sofft. George Chinsee.

While it’s hard to find a more ladylike silhouette than the ballet flat, Paul Mayer Attitudes has redefined it in more masculine terms by adding a delicate wingtip to the iconic style.

What ties them all together, is their focus on ease of wear, incorporating cushioned footbeds, arch supports and flexible outsoles.

Paul Mayer Attitudes Ballet Flats Paul Mayer Attitudes ballet flat with wingtip detailing and bow trim. George Chinsee.