Play with Proportions: The Best Skirt Length–Boot Height Pairings for You to Try

By Andrea Cheng
Updated Oct 28, 2014 @ 10:59 am
Credit: AKM-GSI

We've already mastered fall's unofficial uniform with some insanely chic sweater-and-skirt combos ( 23 of them, in fact), but every great look mandates equally great footwear. And to find the best possible pairing, we took style cues from Hollywood's chicest and chronicled every kind of boot, from over-the-knee to ankle-high, that work best with varying hem lengths.

RELATED: Shop the 35 Best Ankle Boots Around (and At Every Heel Height)

Taylor Swift’s gingham print Oscar de la Renta number may seem demure, thanks to its below-the-knee hemline, but the musician took matters into her own hands and stepped into a pair of sleek Oxford booties. The shape and the skinny heel elongated (rather than shortened) her stems, creating the illusion of enviably long, lean legs.

From shin-grazing frocks to mini thigh-baring shift dresses, find out which complementary star-approved boots go hand-in-hand.

PHOTOS: Play with Proportions: Skirt and Boot Pairings to Try

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Below-the-Knee Pencil + Oxford Booties

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  • Get Taylor Swift's enviable long legs, even in a demure below-the-knee pencil skirt, by stepping into sleek Oxford booties-the shape and heel elongate (rather than shorten) your stems. Shop the look-alike pieces below:
  • Top: Mango, $40; mango.com
  • Skirt: Zara, $60; zara.com
  • Booties: Burberry London, $850; mytheresa.com
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Floral Dress + Over-the-Knee Boots

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  • Learn from supermodel Rosie Huntington-Whiteley and transition your breezy floral dress from summer to fall with over-the-knee boots to limit skin exposure. Shop look-alike pieces below:
  • Dress: HampM, $60; hm.com
  • Boots: Stuart Weitzman, $785; stuartweitzman.com

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Knee-Grazing Pleats + Peep-Toe Booties

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  • Take a style pointer from Olivia Palermo and offset floaty ladylike accordion pleats with modern elements, like a fun waistcoat and cool peep-toe booties. Shop look-alike pieces below:
  • Dress: Madewell, $188; madewell.com
  • Booties: Joie, $315; joie.com
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Tea-Length Column + Center-Slit Bootie

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  • Shin-grazing hems are one of this season's hottest silhouettes. Create the illusion of more leg with a sexy split-front bootie, like Lizzy Caplan's. Shop look-alike pieces below:
  • Top: Jonathan Simkhai, $445; net-a-porter.com
  • Skirt: Sandro, $315; sandro-paris.com
  • Bootie: Vince Camuto, $325; vincecamuto.com

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Striped Shift + Thigh-High Boots

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  • Invite a sliver (just a sliver!) of skin with a mini shift dress and thigh-high suede boots for a casual off-duty look, a la Diane Kruger. Still too revealing for your taste? Shrug on a long overcoat to top it off. Shop look-alike pieces below:
  • Dress: Cos, $69; cosstores.com
  • Boots: Sigerson Morrison, $795; sigersonmorrison.com

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Midi-Length Frock + Open-Toe Booties

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  • Follow in Sarah Jessica Parker's footsteps and toughen up a sweet full midi-length dress with cool cut-out booties. Shop look-alike pieces below:
  • Dress: Mara Hoffman, $298; bonadrag.com
  • Booties: Vince, $395; vince.com
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Knee-Grazing Dress + Tall Riding Boots

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  • Own a relaxed bohemian-inspired frock like Chrissy Teigen's? Prep it for cooler weather by pairing it with an elegant stacked-heel over-the-knee boot. Shop look-alike pieces below:
  • Dress: Wilfred, $175; aritzia.com
  • Boots: Louise et Cie, $298; vincecamuto.com
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