Fashion Challenge: How To Style Skirts Over Pants

The last time you wore a skirt or dress over pants in good conscience was most likely to an Avril Lavigne concert...with flip-flops, braces, and a terrycloth wristband, no less. These days, there's probably no other layering technique that'll elicit such extreme, knee-jerk negativity than wearing a skirt or dress over a pair of trousers — and for good reason. The past iterations of the trend — boot-cut denim with babydoll dresses, work slacks with sweater dresses, cargo pants with fitted jersey wraps — were pretty heinous.
Good thing recent runway ensembles have provided sleek, not sloppy, innovations to this look, convincing us to reconsider. Sure, they look good on models, but can they handle the real-life streets? We tested out five different ways to wear this layering trend. How did we do?
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Monochrome — Match your dress to your pants for one sleek look.

Opening Ceremony Cerulean/Green Double Faced Skipper Gazaar Dress, $449, available at Opening Ceremony; M Missoni Dropped Trouser, $308.01, available at My-Wardrobe; Tibi Ida Sandals in White, $445, available at Tibi.
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How striking is this cobalt blue?
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Get Playful With A Peplum — Add some definition to your waist by putting a peplum dress or skirt over your pants (or, in this case, skinny jeans) for an ultra-feminine ensemble.

Acne Mape Petite Cropped Leather Biker Jacket, $1,350, available at My-Wardrobe; Ganni Herringbone Peplum Dress, $206.25, available at My-Wardrobe; Sandro Pirate Pants, $305, available at Sandro; Tibi Shane Heels in Black, $435, available at Shopbop.
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It also helps to include one pattern in the combo — choose either a printed peplum or cropped trousers!
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Hey, Shorty — Have a dress that's a little more tunic than frock? Pair it with you favorite pair of jeans and booties for a super-cute spring weekend look.

Tibi Checkered Dropwaist Dress, $445, available at Tibi; Comptoir des Cotonniers Blue Ouvelle Jeans, $141, available at Comptoir des Cotonniers; Won Hundred Three Boots, $309.95, available at Solestruck.
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This drop-waist ruffle is sweet without being saccharine.
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Play Around With Midi – A long, loose midi-skirt gets a little more structure with a pair of pants underneath.

Comptoir des Cotonniers Mint Oakes Jacket, $288.34, available at Comptoir des Cotonniers; Band of Outsiders Cropped Top in Sky Blue, $315, available at Saks; Band of Outsiders Wrap Skirt w/ Pleated Inset in Sky Blue, $585, available at Saks; Current/Elliot The Stiletto Sun Bleached Jeans, $168, available at Shopbop; Zara Metallic Sandals, $79.90, available at Zara.
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Matching your pants to your jacket helps connect everything together and makes the outfit feel way more deliberate.
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Peekaboo, We See You! — Sheers, open weaves, laces...all of these slightly see-through skirts and dresses make for great top layers that aren't the least bit heavy. This is a great place to start for commitment-phobes.

Tibi Basia Lace Dress, $695, available at Tibi; Wes Gordon Black Cigarette Pants, $750, available at Bergdorf Goodman; Cole Haan Paley High Sandal, $228, available at Cole Haan.
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Convinced yet?