Why You Should Wear Menswear Shoes with Everything

Borrowing from the boys is not, by any means, an original concept, especially not since Diane Keaton made it effortlessly cool in Annie Hall or every time a French girl would drape her boyfriend's blazer over her shoulders or clasp her father's watch around her wrist. And these days, menswear, womenswear—it's all one giant blur in today's gender-fluid, free-for-all, androgyny-happy society. Yet, there's still something to be said about the quintessential girl-boy pairing of all time: a pretty, flirty dress anchored by a pair of I-mean-business brogues.

It's a classic combo so maddeningly simple, it's no wonder it continues to prevail, regardless of season, year, or what's "on-trend." It achieves the same effect as throwing on a leather jacket to toughen up a delicate top or gripping a briefcase-like purse to add structure to a soft silhouette, but stepping into wingtip brogues or two-tone Oxfords brings a degree of versatility and functionality that the others lack. Versatile, in that, as Victoria Beckham pointed out to us on her fall/winter 2016 runway, menswear-inspired brogues can complement a look as formal as an evening dress or as casual as sporty separates (pictured, above). And functional, in the sense that your feet won't turn against you after a particularly active day (no heels, no arches, no pain). With that said, we present to you a very practical (and very chic) present—five ways to integrate menswear-inspired shoes into your wardrobe. 

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An Asymmetrical Skirt + Striped Brogues 

Flash a hint of leg with an asymmetric skirt, but counter that hit of sexiness with a pair of polished brogues (we love solids, but even we can't resist playful stripes). 

Joseph skirt, $430; joseph-fashion.com. Robert Clergerie shoes, $550; zappos.com. 

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A Denim Pencil Skirt + Derby Shoes

Only a pair of eccentrically cool green croc derby shoes (with a contrasting detachable fringe!) can give something as classic as a clean-cut denim skirt a healthy dose of quirk. 

A.P.C. skirt, $135; apc.fr. Marni shoes, $710; marni.com. 

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A Shirtdress + White Chunky Derbies

Kick up the drama with white statement-making derbies with a thick rubber sole (conducive for stomping) that won't compromise professionalism, especially when paired with a modest shirtdress.

Ganni dress, $31; mytheresa.com. Balenciaga shoes, $578 (originally $1,255); fwrd.com. 

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Fit-and-Flare Dress + Penny Loafers

Unless it's Halloween (and even then), skip the plaid and, for the love of God, the knee-high socks, to avoid being mistaken for a schoolgirl. For a sophisticated, grown-up take, pair your penny loafers with a cool tie-sleeve, mock-neck dress in a spicy shade, like paprika.

Tibi dress, $395; tibi.com. Bass shoes, $110; ghbass.com. 

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Knit Dress + Oxford d'Orsay Flats

Achieve cool-girl swagger with a textured knit dress with a patent Oxford-slash-d'Orsay flat hybrid.

Isabel Marant dress, $405; net-a-porter.com. Nine West shoes, $89; macys.com. 

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  • By Andrea Cheng (Text) and Steffi Lee (Market)
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