Why You Should Wear Menswear Shoes with Everything

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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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