How To Wear Over-The-Knee Boots The Right Way

When it comes to intimidating accessories, over-the-knee boots may well take the cake. What woman in her right mind wants to invite references to Pretty Woman? That said, in the fashion world, often times the greatest risks yield the biggest rewards. And let’s be honest: while your trusty ankle boots are incredibly versatile, will they ever turn heads? Not so much.

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    An over-the-knee boot, on the other hand, is guaranteed to garner a response, and I have a few key tips to make sure the reception is stellar. Read on for the secrets to styling the bold boot so it looks as sophisticated and chic as you are—promise.

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    PHOTO: Photographer: Curtis Buchanan

    Over-the-knee boots were practically made for miniskirts. A slight sliver of leg (limit it to two inches) breaks up the long boot and adds the perfect dose of allure. For styling, I opted for a grunge-meets-schoolgirl look that tempers the boots’ overtly provocative nature.

    What I Wore:
    French Connection Belle Boucle Wool Coat ($348) in Sierra; Smythe Reissue Schoolboy Blazer ($695) in Black; Junk Food Clothing Co. The Breakfast Club Coffeehouse Color Block Tee Shirt ($40) in Electric White/Overwashed; Reformation Echo Skirt ($138); Stuart Weitzman The Highland Boots ($750) in Black Suede; Coal Thrift Knit Beanie ($30) in Red; Bing Bang Lightning Bolt Stud Earrings ($42) in Silver; Gorjana Damsel Necklace ($60) in Gold; Matt & Nat Brace Backpack ($125) in Black.

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    PHOTO: Photographer: Curtis Buchanan

    Not only is a backpack pleasantly practical—it’s less fussy than even a cross-body bag—it also adds some laid-back appeal to the look.

    What I Wore:
    French Connection Belle Boucle Wool Coat ($348) in Sierra; Smythe Reissue Schoolboy Blazer ($695) in Black; Junk Food Clothing Co. The Breakfast Club Coffeehouse Color Block Tee Shirt ($40) in Electric White/Overwashed; Reformation Echo Skirt ($138); Stuart Weitzman The Highland Boots ($750) in Black Suede; Coal Thrift Knit Beanie ($30) in Red; Matt & Nat Brace Backpack ($125) in Black.

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    PHOTO: Photographer: Curtis Buchanan

    The perfect way to balance the primness of a tailored coat? Pair it with a hoodie and knit beanie, of course.

    What I Wore:
    French Connection Belle Boucle Wool Coat ($348) in Sierra; Smythe Reissue Schoolboy Blazer ($695) in Black; Junk Food Clothing Co. The Breakfast Club Coffeehouse Color Block Tee Shirt ($40) in Electric White/Overwashed; Coal Thrift Knit Beanie ($30) in Red; Bing Bang Lightning Bolt Stud Earrings ($42) in Silver; Gorjana Damsel Necklace ($60) in Gold.

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    PHOTO: Photographer: Curtis Buchanan

    Little details, like the enticing leather ties in the back, make these Stuart Weitzman boots a standout pick.

    What I Wore:
    Reformation Echo Skirt ($138); Stuart Weitzman The Highland Boots ($750) in Black Suede.

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    PHOTO: Photographer: Curtis Buchanan

    Showing a little leg feel a bit much? Try styling the boots with a pair of skinnies instead. Your jeans should ideally have a tight fit with a bit of stretch, and a grey color adds just enough contrast while creating the illusion of never-ending legs.

    What I Wore:
    Joe’s Jeans Opale Jacket ($368) in Ink; H&M Denim Shirt ($25) in Indigo Blue; D-ID Florence Ankle Skinny Jeans ($158) in Blue Black; BCBGMAXAZRIA Metal Chevron Stone Necklace ($88) in Silver; Baublebar Open Bangle Set ($22); Simone Camille The Dash Clutch ($274) in Jaguar Print; Stuart Weitzman The Highland Boots ($750) in Black Suede.

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    PHOTO: Photographer: Curtis Buchanan

    Leopard print plus an oversized leather tassel feels a little bit naughty, in the best way.

    What I Wore:
    H&M Denim Shirt ($25) in Indigo Blue; D-ID Florence Ankle Skinny Jeans ($158) in Blue Black; Baublebar Open Bangle Set ($22); Simone Camille The Dash Clutch ($274) in Jaguar Print; Stuart Weitzman The Highland Boots ($750) in Black Suede

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    PHOTO: Photographer: Curtis Buchanan

    The incredible plume-like texture on this midnight blue coat puts my outfit in the eveningwear  category.

    What I Wore:
    Joe’s Jeans Opale Jacket ($368) in Ink; H&M Denim Shirt ($25) in Indigo Blue; BCBGMAXAZRIA Metal Chevron Stone Necklace ($88) in Silver.

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    PHOTO: Photographer: Curtis Buchanan, Sittings Editor: Michelle Scanga
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    Calvin Klein Averie Over-The-Knee Convertible Leather Boots ($199) in Black

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    Sigerson Morrison Llane Over the Knee Boots ($795) in Black

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    Jean-Michel Cazabat Panpan Suede Over the Knee Boots ($485) in Black

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    Alice + Olivia Dae Over the Knee Boots ($695) in Black

Shop this Story
Dae Over the Knee Boots

Dae Over the Knee Boots

Alice + Olivia, $695
SHOP
Llane Over the Knee Boots

Llane Over the Knee Boots

Sigerson Morrison, $795
SHOP
Panpan Suede Over the Knee Boots

Panpan Suede Over the Knee Boots

Jean-Michel Cazabat, $485
SHOP
Averie Over-The-Knee Convertible Leather Boots

Averie Over-The-Knee Convertible Leather Boots

Calvin Klein, $199
SHOP
Mazzarine High Heel Pointed Toe Over The Knee Boots

Mazzarine High Heel Pointed Toe Over The Knee Boots

B Brian Atwood, $695
SHOP
The Highland Boots

The Highland Boots

Stuart Weitzman, $750
SHOP
Belle Boucle Wool Coat

Belle Boucle Wool Coat

French Connection, $348
SHOP
Brace Backpack

Brace Backpack

Matt & Nat, $125
SHOP
The Breakfast Club Coffeehouse Color Block Tee Shirt

The Breakfast Club Coffeehouse Color Block Tee Shirt

Junk Food Clothing Co., $40
SHOP
Echo Skirt

Echo Skirt

Reformation, $138
SHOP
Reissue Schoolboy Blazer

Reissue Schoolboy Blazer

Smythe, $695
SHOP
Damsel Necklace

Damsel Necklace

Gorjana, $60
SHOP
Damsel Necklace

Damsel Necklace

Gorjana, $60
SHOP
Knit Beanie

Knit Beanie

Coal Thrift, $30
SHOP
Opale Jacket

Opale Jacket

Joe’s Jeans, $368
SHOP
Denim Shirt in Indigo Blue

Denim Shirt in Indigo Blue

H&M, $25
SHOP
Florence Ankle Skinny Jeans

Florence Ankle Skinny Jeans

D-ID, $158
SHOP
The Dash Clutch

The Dash Clutch

Simone Camille, $274
SHOP
Metal Chevron Stone Necklace

Metal Chevron Stone Necklace

BCBGMAXAZRIA, $88
SHOP
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