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Dresses to Wear With Thigh-High Boots

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There’s nothing like a dress and a good pair of boots to make you stylish. But let’s be honest, thigh-high boots can be tricky to style without making you look like a pole dancer.

So we’ve pulled together some outfits to make sure you look sophisticated and classy in your thigh-highs.

We’ll look at several great dresses to wear with thigh-high boots.


Are Over-The-Knee Boots In Style?

They are indeed, and while you should have a variety of different boots and shoes in your footwear arsenal, thigh-high boots are making a statement this fall. But there are a few dos and don’ts you should keep in mind:

DO

  • Go for a block heel.
  • Show some skin between your hemline and the top of your boot.
  • Wear tights if it’s really cold.
  • If in doubt, match the tights to your boots, not your dress.

DON’T

  • Go super tight with the dress, unless you are pairing it with a vest, jacket, or wrap of some sort.
  • Go for stilettos with pointy toes
  • Do platform thigh highs… it’s just too much.
  • Wear thigh-high boots in the middle of summer – wait for the right season!

Dresses to Wear With Thigh-High Boots

We have put together 10 of the best dress and thigh-high boot looks for you, and we’ll show you how you can put them together.

Look 1 – Fall Boho Casual

Boho will never go out of fashion. Geometric prints, fringed handbags, and anything with a 70s retro feel play into the boho vibe. A long-sleeved, printed tunic in the dark, rich colors of the season and thigh-high boots in beige suede are a perfect combo.

Credit: Instgram / currentlycaro

Here’s how to put this look together:

Women Boots Winter Over Knee Long Boots Fashion Boots Heels Autumn Quality Suede Comfort Square Heels US Size (Brown 2 Inch, numeric_5_point_5)
Women Boots Winter Over Knee Long Boots Fashion Boots Heels Autumn Quality Suede Comfort Square Heels US Size (Brown 2 Inch, numeric_5_point_5)
Boots Use New wedge square heels,special design for ladies who can not stand on stiletto; the boots ware comfortable like flats,fit running and long time walking.
Sale
Small Fringe Crossbody Bag with Wrist Strap (Tan)
Small Fringe Crossbody Bag with Wrist Strap (Tan)
8" (W) x 5.5" (H) x 3" (D); Zipper closure; Adjustable shoulder strap with 27" drop & 8.5" detachable wrist strap
$18.95

Look 2 – Belted Button-Down Dress With Over-The-Knee Boots

A belted button-down dress is always classic and looks great paired with gorgeous thigh-high boots. The belt is key if you want a more sophisticated look, as opposed to looking like you left the house and forgot to put your pants on.

Credit: Instgram / alwayson_chic

Here’s how to put this look together:


Look 3 – Off the Shoulder T-shirt Dress and Leather Wrap Belt

Again here, the belt here is key to making this a more polished outfit.

Credit: Instgram / alwayson_chic

Here’s how to put this look together:

Romwe Women's Asymmetrical Off Shoulder Long Sleeve Casual Tunic Dress Tee Dress with Pockets Burgundy S
Romwe Women's Asymmetrical Off Shoulder Long Sleeve Casual Tunic Dress Tee Dress with Pockets Burgundy S
Fabric is stretchy, very soft and comfortable to wear; Looks great with most kinds of shoes and bags and let you feel comfortable all the day
$21.99
FASHIONGEN - Woman Italian leather Obi belt, CASSIANE - Beige, S-M
FASHIONGEN - Woman Italian leather Obi belt, CASSIANE - Beige, S-M
★Width of the belt : Maximum width of the belt 3.15 inches; ⚠For a Better Fit :Choose your size by following our size guide in the description.
Sale
Vince Camuto Women's Palley Over-The-Knee Boot, Cashew, 5
Vince Camuto Women's Palley Over-The-Knee Boot, Cashew, 5
croco embossed leather; square island heel; inside zipper; almond toe
$103.13
Hycurey Oversized Clutch Bag Purse and Handbag Womens Large PU Leather Evening Wristlet Handbags (Winered)
Hycurey Oversized Clutch Bag Purse and Handbag Womens Large PU Leather Evening Wristlet Handbags (Winered)
Material: High quality PU material, durable design, can be used for a long term.; Oversized Clutch Size: (L)13 x (W)0.8x (H)9.4 inches; about 0.5 pounds weight.
$13.99

Look 4 – Sweater Dress with Faux Fur Jacket

The sweater dress should be a staple piece in your closet this year. Not only are they comfy and warm, but they look great with over-the-knee boots.

Add to that a faux fur cropped jacket and a snakeskin patterned bag for a totally chic and well-put-together look. Word to the wise… animal prints are also going to be a hot commodity this fall.

Credit: Instgram / alwayson_chic

Here’s how to put this look together:


Look 5 – 2-Tone Skater Dress with Leather Jacket

Skater dresses are super hot style, and they don’t look like they’re going anywhere anytime soon. A 2-toned skater dress gives you the look of separates without the hassle.

You could just as easily get this look from a separate top and a skater skirt.

A black top and black boots with a cropped black leather jacket are a classic combo. With the skirt in a different color or pattern, you will break things up a bit and add a little interest to your ensemble.

Credit: Instagram / janinewiggert

Here’s how to put this look together:

Sale
SweatyRocks Women's Long Sleeve Tunic Dress Color Block Plaid Dress with Belt Black and White XS
SweatyRocks Women's Long Sleeve Tunic Dress Color Block Plaid Dress with Belt Black and White XS
Please refer to the size measurement in image before ordering (Not Amazon size chart)
$14.99
MakeMeChic Women's Casual Faux Leather Jacket Zip Up Long Sleeve Cropped Pleather Moto Biker Coat Outerwear Black L
MakeMeChic Women's Casual Faux Leather Jacket Zip Up Long Sleeve Cropped Pleather Moto Biker Coat Outerwear Black L
The PU leather fabric has no stretch, but it's soft and comfortable; Model Measurements: Height: 68.5inch, Bust: 35.8inch, Waist: 23.2inch, wear size S
$49.99
Sale
Women's Soft Faux Leather Tote Shoulder Bag from Dreubea, Big Capacity Tassel Handbag Black New S
Women's Soft Faux Leather Tote Shoulder Bag from Dreubea, Big Capacity Tassel Handbag Black New S
Faux leather; 1 main big pocket & 1 small side pocket; For daily use, traveling, working, shopping, school, etc. Gift ideas.
$14.79

Look 6 – Billowy Sweater Dress

Sweater dresses of all shapes and styles are great for fall and winter, and none comfier than this version! It is like your favorite, most comfy sweater… just a little longer.

All you need to do is put on a pair of thigh-high boots and you’ve got an instant outfit with only 2 pieces of clothing! Low maintenance, comfortable and stylish.

Those are three words that aren’t used very often in the same sentence.

Credit: Instagram / glamarosh

Here’s how to put this look together:


Look 7 – Long Sleeve Ruched Dress and Oversized Scarf Wrap

There’s nothing like bold color to ring in the new season and this orange, ruched dress does this perfectly. The oversized scarf doubles as a wrap for when the weather gets a little chilly.

And when you pair those with taupe suede thigh-high boots, you’ve got yourself an outfit. Taupe is one of those colors that goes with everything, so you will get more use out of a neutral-colored boot, like taupe, black or brown because they will go with more outfits.

Credit: Instagram / dtkaustin

Here’s how to put this look together:


Now if there is one thing you simply must have in your closet, especially if you are planning on getting a pair of thigh-high boots, it’s a black turtleneck mini dress.

It’s so versatile that we are going to show you how to style it in three different ways with thigh-high boots:

Look 8 – Black Turtleneck Mini Dress and ¾ Length Overcoat with Statement colored Boots

There’s no denying that a neutral boot will go with more outfits, but a thigh high boot in a statement color like royal blue is epic when you style them out with black. And who said you only have to have only one pair?!

Credit: Instagram / wendyslookbook

Here’s how to put this look together:

Sale
ANRABESS Womens Turtleneck Long Sleeve Slim Bodycon Pullover Sweater Dress A145hei-M Black
ANRABESS Womens Turtleneck Long Sleeve Slim Bodycon Pullover Sweater Dress A145hei-M Black
Washing Instruction: Hand wash cold only.Do not bleach or iron.
$44.99
Sale
Bankeng Women Winter Wool Blend Camel Mid-Long Coat Notch Double-Breasted Lapel Jacket Outwear (Small, Black)
Bankeng Women Winter Wool Blend Camel Mid-Long Coat Notch Double-Breasted Lapel Jacket Outwear (Small, Black)
Button closure; Material: high-quality wool and polyester fabric, breathable, comfortable and warm to wear
$58.78
Top Handle Faux Suede Clutch, Royal Blue
Top Handle Faux Suede Clutch, Royal Blue
Length : 11.5 inches, Width : 2 inches, Height : 7.5 inches; Comes with 21" drop crossbody chain (detachable)
$45.95

Look 9 – Black Turtleneck Mini with Faux Fur Vest

A black turtleneck mini looks fantastic with a faux fur vest and black over-the-knee boots.

Credit: Instagram / itsmsmonica

Here’s how to put this look together:


Look 10 – Black Turtleneck Mini with Cape Poncho

If you don’t already have one, a cape poncho for the fall and winter seasons is definitely a good investment. They look great.

They also happen to go fantastically well with thigh-high boots and a black turtleneck mini. Incidentally, jeans and a poncho also look great with over-the-knee boots.

Credit: Instagram / brittanyxavier

Here’s how to put this look together:

Sale
ANRABESS Womens Turtleneck Long Sleeve Slim Bodycon Pullover Sweater Dress A145hei-M Black
ANRABESS Womens Turtleneck Long Sleeve Slim Bodycon Pullover Sweater Dress A145hei-M Black
Washing Instruction: Hand wash cold only.Do not bleach or iron.
$44.99
Women Boots Winter Over Knee Long Boots Lace Up Fashion Boots Heels Autumn Quality Suede Comfort Square Toe US Size (B Black Lace up, numeric_7)
Women Boots Winter Over Knee Long Boots Lace Up Fashion Boots Heels Autumn Quality Suede Comfort Square Toe US Size (B Black Lace up, numeric_7)
Boots Use New wedge square heels,special design for ladies who can not stand on stiletto; the boots ware comfortable like flats,fit running and long time walking.
$46.99
Women's Vintage Pattern Open Front Poncho Cape Shawl (Series 18-Black)
Women's Vintage Pattern Open Front Poncho Cape Shawl (Series 18-Black)
One size: Length 59inch,Width 51.2inch; Super cozy oversized scarves & wraps design,fashionable and elagant
$31.86
Silver Fever® Leather Buckle Flap Hobo Handbag (burgundy)
Silver Fever® Leather Buckle Flap Hobo Handbag (burgundy)
Silver Fever Brand; Brown Genuine Leather; Measures Approx: 11.5" x 8.5" x 3", 17" Adjustable Strap
$35.00

Conclusion

So there you have it. You’ll never be wondering what dresses to wear with thigh-high boots. We’ve just given you 10 ways to style over-the-knee boots with a dress and provided a few tips along the way to make sure your thigh-high boot look is more chic than cheap.

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