Thigh-High Boots: A Shopping and Styling Guide

Kristen Bousquet
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STYLECASTER | Thigh-High Boots Shopping Guide
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Photo: Getty Images

If you’re fed up with the cold, grabbing yourself a pair of thigh-high boots can a lifesaver (for your shivering body, as well as your style standards). These sky-high boots do more than add an alluring touch to any outfit. They’re the ideal option for those days when you want to wear a pair of black boots, but need an extra layer of warmth. Practical and chic? Count us in.

MORE: 80 Outfit Ideas to Freshen Up Your Winter Work Wardrobe

Thigh-high boots also instantly dress up any look. Wearing an oversized sweater and leggings doesn’t exactly seem like a work outfit, but add a pair of high boots and instantly you look more office-ready. Yes, we just said thigh-high boots are acceptable when you’re heading to work—as long as you’re also wearing thick tights or skinny pants underneath.

Ahead, check out the best ways to style sky-high, thigh-high boots—and the prettiest picks to buy now.

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STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Black Thigh High Boots
Photo: Getty
STYLECASTER | Winter Boots | Thigh High Boots | Loeffler Randall Suede Over-the-Knee Boots

Loeffler Randall suede over-the-knee boots, $248 at The Outnet

STYLECASTER | Winter Boots | Thigh High Boots | Dolce Vita Emmy black studded suede thigh high boots

Dolce Vita Emmy black studded suede thigh high boots, $200 at TOBI

STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Black Thigh High Boots
Photo: Getty
STYLECASTER | Winter Boots | Thigh High Boots | Chinese Laundry Krush pink suede over the knee boots

Chinese Laundry Krush pink suede over the knee boots, $99 at Lulus

STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Black Thigh High Boots
Photo: Getty
STYLECASTER | Winter Boots | Thigh High Boots | Alias Mae Zues velvet boot

Alias Mae Zues velvet boot, $400 at Alias Mae

STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Black Thigh High Boots
Photo: Getty
STYLECASTER | Winter Boots | Thigh High Boots | Steve Madden Slammin black over the knee boots

Steve Madden Slammin black over the knee boots, $129 at Lulus

STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Red Thigh High Boots
Photo: Getty
STYLECASTER | Winter Boots | Thigh High Boots | TOBI Mixed Signals black satin thigh high boots

TOBI Mixed Signals black satin thigh high boots, $108 at TOBI

STYLECASTER | Winter Boots | Thigh High Boots | Rue 21 taupe open toe thigh high boots

Rue 21 taupe open toe thigh high boots, $40 at Rue 21

STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Orange Thigh High Boots
Photo: Getty
STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Neutral Thigh High Boots
Photo: Getty
STYLECASTER | Winter Boots | Thigh High Boots | Akira over the knee boots

Akira over the knee boots, $58 at Dolls Kill

STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Pink Thigh High Boots
Photo: Getty
STYLECASTER | Winter Boots | Thigh High Boots | FABI over the knee boots

FABI over the knee boots, $769 at Farfetch

STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Orange Thigh High Boots
Photo: Getty
STYLECASTER | Winter Boots | Thigh High Boots | Free People Paris over the knee boot

Free People Paris over the knee boot, $228 at Revolve

STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Red Thigh High Boots
Photo: Getty
STYLECASTER | Winter Boots | Thigh High Boots | Sorry to Bug Ya thigh high boot

Sorry to Bug Ya thigh high boot, $90 at Nasty Gal

STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Black Thigh High Boots
Photo: Getty

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  • STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Black Thigh High Boots
  • STYLECASTER | Winter Boots | Thigh High Boots | Loeffler Randall Suede Over-the-Knee Boots
  • STYLECASTER | Winter Boots | Thigh High Boots | Dolce Vita Emmy black studded suede thigh high boots
  • STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Black Thigh High Boots
  • STYLECASTER | Winter Boots | Thigh High Boots | Chinese Laundry Krush pink suede over the knee boots
  • STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Black Thigh High Boots
  • STYLECASTER | Winter Boots | Thigh High Boots | Alias Mae Zues velvet boot
  • STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Black Thigh High Boots
  • STYLECASTER | Winter Boots | Thigh High Boots | Steve Madden Slammin black over the knee boots
  • STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Red Thigh High Boots
  • STYLECASTER | Winter Boots | Thigh High Boots | TOBI Mixed Signals black satin thigh high boots
  • STYLECASTER | Winter Boots | Thigh High Boots | Rue 21 taupe open toe thigh high boots
  • STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Orange Thigh High Boots
  • STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Neutral Thigh High Boots
  • STYLECASTER | Winter Boots | Thigh High Boots | Akira over the knee boots
  • STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Pink Thigh High Boots
  • STYLECASTER | Winter Boots | Thigh High Boots | FABI over the knee boots
  • STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Orange Thigh High Boots
  • STYLECASTER | Winter Boots | Thigh High Boots | Free People Paris over the knee boot
  • STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Red Thigh High Boots
  • STYLECASTER | Winter Boots | Thigh High Boots | Sorry to Bug Ya thigh high boot
  • STYLECASTER | Winter Boots | Thigh High Boots | Street Style Star Wearing Black Thigh High Boots

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