How To Wear a Midi Pencil Skirt

Midi pencil skirt + sweater

While I love a good sweater/skirt outfit, some combos are definitely trickier to wear than others. It has less to do with the reality of the situation and more to do with the mental block that often accompanies avant-garde silhouettes. An unconventional pairing cues the risk aversive side of my brain: "That shapeless sack of a skirt? Really? We think that's going to look good?" And my inner critic definitely kicked up a fuss when I tried on this midi pencil skirt with my favorite oversized sweater.

Oversized turtleneck sweater

Because really, if you stop to think about it, this outfit shouldn't work. A big long top over a big long bottom, both of them characterized by straight lines, should signal 'high school English teacher' to anyone within eyeshot. Yet as always, the details save the day. Both items lightly skim the body to hint (but not hug) the figure beneath it. Modest hem slits provide movement as well as interest. Narrow arms on the sweater further counteract the frump factor.

Midi pencil skirt

"Sounds fine on paper," cries the naysayer brain, "but what about in practice?" Indeed, no amount of persuasive descriptors can convince a our conservative sides to stray from the safe route. That's the point at which you just have to slip on the confounding item (the midi skirt, yes, but also culottes! a tunic dress!) and take a leap of faith out the door. At worst you'll feel awkward for a few hours, and at best you'll garner some compliments for your ingenuity and panache—and have a fun new look for your repertoire. And who's in charge here really? It's time to show that naysayer brain who's boss!

Outfit Guide: Hatch Collection Sweater. Oak + Fort Midi Skirt. Yosi Samra Booties. Prismera Design and Katie Dean Jewelry Rings. Parc Boutique Envelope Clutch. Photos: Sarah Hrudka Photography

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