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5 Ways Celebs Wear Women’s Over the Knee Boots This Winter

It can be hard to bridge the gap between classy, and well, not so classy, with women’s over the knee boots. Wearing the thigh-high boot can be a bit intimidating, as it has historically had a risqué stigma attached to it. And, perhaps this is the reason why purchasing women’s over the boots is such a risky investment for many gals.  So how do you take something that has so much attitude and sex appeal and make it elegant and fun for an everyday outfit? Well, thankfully many stylish celebrities like Kristin Cavallari and Aimee Song have exemplified just how to nail these trends without any risky business involved, ahem, remember those famous thigh high boots that Julia Roberts wore in Pretty Woman? That’s right, we’re going to show you how to wear women’s over the boots in a chic street style manner plus we have some tips to choosing the right boots for your body type.

Whether you seek leather over the knee boots or soft suede over the knee boots, here are a few key tips to remember when searching for the perfect thigh-high boot.

  • Tip 1 –Find a pair that is fitting to your height. The length of the material from the heel to thigh is definitely a factor to consider.  In general, the top of the boot should end just above (about an inch or so) above the knee.  You don’t want to purchase a boot that your legs will be drowning in.
  • Tip 2 — Invest in a high quality material.  Because the over-the-knee has so much material, you want to make sure this material is one of quality. Hence, for a polished and clean look, avoid low-quality material such as PVC leather and cheap looking, faux suede.
  • Tip 3 — Have fun with it! This style is such a statement, you don’t want to miss out on an opportunity to wear something with so much sass. Pick a soft leather or brushed suede in a color that best suits you.

Below, shop our favorite brands of women’s over the knee boots and get inspired by 5 fashionistas killing this season’s most risqué, but fabulous, shoe trend.


How To Wear Women’s Over the Knee Boots

1. Monochromatic

Loving Ashley Madekwe’s pale blue color scheme with a bright red cross-body. Oh yeah, and her Stuart Weitzman suede over the knee boots.

SHOP ASHLEY’S BOOTS: Stuart Weitzman ‘Highland Suede Over-the-Knee Boot, Topo’

Photo Credit: Ashley Madekwe's Instagram

Photo Credit: Ashley Madekwe’s Instagram

Shop the full look below:

2. Sporty

Kristin Cavallari recently showed her sporty support for her husband, Jay Cutler, of the Chicago Bears, as she sported an oversized team sweater with her Chinese Laundry suede over the knee boots.  One of the easiest go-to tops during the winter is the oversized sweater — it looks great on many body types and can be dressed up with a pair of skinny jeans or leather leggings.

SHOP KRISTIN’S BOOTS: Chinese Laundry ‘Cassie Over the Knee Boot’

Photo Credit: Kristin Cavallari's Instagram

Photo Credit: Kristin Cavallari’s Instagram

3. Poncho

Ponchos are one of the most sought after items this season, so what better way than to incorporate the best of both pieces?   See more fab winter coats here.  Layer a pair of winter-y, plaid shorts with a patterned poncho, slip on a pair of sleek black, suede over the knee bootsm and you’ll be just as stylish as Olivia Palermo in her colorblock, monogram Burberry cape amazingness.

SHOP OLIVIA’S PONCHO (very similar): Burberry Prorsum Mega Check Cape

Photo Credit: Tumblr Images; Olivia Palermo in black, suede knee high boots.

Photo Credit: Tumblr Images; Olivia Palermo in black, suede over the knee boots.

Shop a similar look to Olivia, below:


4. Everyday Casual

Mixing the ultimate lazy tee with “it” designer items can be quite sassy for an everyday look. Model, Chrissy Teigen, recently wore her cognac Celine Phantom tote with a pair of brown Phillip Lim leather over the knee boots in the same hue. Love!

SHOP CHRISSY’S BOOTS: ‘3.1 Phillip Lim Ora Closed Toe Boots’


Photo Credit: Tumblr Images

Shop Chrissy’s look, below:

5. Kimono

Style blogger, Aimee Song of Song of Style, wore her Jimmy Choo leather over the knee boots with a colorful kimono, jeans, and Phillip Lim handbag. The long and sleek lines of this kimono and thigh high boot combination help to elongate her petite figure. Try wearing a long trench coat instead of a kimono for a more timeless and sophisticated look.

SHOP AIMEE’S BOOTS: Jimmy Choo ‘Turner Stretch Leather Thigh Boots’

Photo Credit: Song of Style's Instagram

Photo Credit: Song of Style’s Instagram

Shop Aimee’s look, below:

 Shop Women’s Over The Knee Boot Styles

About The Author

Kara Roudenbush is an experienced digital marketer, fashion blogger and international travel enthusiast. Growing up in San Diego, she has become privy to the coast and the laidback lifestyle within it. She is committed to sharing her passion for style trends and has a constant sweet tooth.

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