What Dress To Wear With Thigh High Boots? [6 Stunning Options Explored!]

We may get commissions for purchases made through links in this post. 

As the end of the year comes closer and the summer heat finally fades away, you might be thinking about cute fall outfits, like dresses with thigh-high boots. Or perhaps you need a gorgeous outfit for a night out on the town. Even simple dresses look alluring when complemented by thigh-high boots!

Thigh-high boots can highlight dresses in an edgy, sophisticated way. You need to select the right type of dress! We have some cute outfits for you to try, such as—

  • Pretty in Pink
  • Cozy Cream Dress
  • Sophisticated All-Black
  • Posh White and Gray
  • Charming Navy Dress
  • Classic Black and White

Besides, are thigh-high boots still in style? Are they appropriate to wear for a wedding or even work? How do you keep them held up? Is it okay to wear them in the summer? Keep reading to find out!

Thigh high boots worn by a woman lying on the couch, What Dress To Wear With Thigh High Boots? [6 Stunning Options Explored!]

Pretty in Pink

If you want to embody the classic Pretty in Pink starring Molly Ringwald, you should try this pastel pink outfit. Gorgeous beige thigh-high boots complement this delicate, silky dress with a matching coat. And the matching silk pink choker completes the look!

Any beige or nude thigh-high boot would go great with a light pink dress. If you’re feeling adventurous, you could try this nude faux leather thigh-high boot.

Click here to see these on Amazon.

Cozy Cream Dress

Generally, sweater dresses are a go-to staple outfit for thigh-high boots. Here is a beautiful cream sweater dress with dark black, silky thigh-high boots. It’s perfect for a winter date night.

Try out this comfy sweater in apricot. Click here to see it on Amazon. 

Sophisticated All-Black

Does your wardrobe consist mainly of black? Don’t worry; it’s not a bad thing! Black is classy and sophisticated. This black velvet dress appears simple, but it hugs the curves and compliments the tiny waist. Plus, the continuation of black thigh-high boots elongates the legs.

Here is a similar velvet black dress with synched waist. Click here to see it on Amazon. 

Posh White and Gray

A cocktail date with the girls might be to celebrate this outfit. This simple white dress is complemented by a taupe jacket and taupe thigh-high boots. Indeed, it’s a dress that will turn heads.

Here is a similar khaki jacket that would go great with this outfit. Click here to see it on Amazon.

Charming Navy Dress

If it’s too warm for sweaters but too cool for T-shirts, then this outfit is the one. The dark navy, elbow sleeve sweater dress compliments the light brown purse with matching light brown thigh-high boots. Also, the chunky turtleneck appears cute and playful. Overall, the dress is the star of this outfit! It’s simple, classic, yet chic.

Check out this similar turtleneck navy dress that will keep you nice and cozy. Click here to see it on Amazon.

Classic Black and White

Does this outfit make you want to strut down the street singing Nancy Sinatra’s “These Boots Are Made for Walking”? If so, then this is the perfect outfit for you! A classic black dress goes with almost all events. And the pure white thigh-high boots portray a sense of fun and carefreeness.

Set a lovely tone to your day, and try a pair of white thigh-high boots. Click here to see them on Amazon. 

Are thigh-high boots still in style?

A woman wearing thigh high boots and high heels

Yes, thigh-high boots are still in style in 2021. Many celebrities rock thigh-high boots.

When you think of thigh-high boots, you might picture Julia Roberts in Pretty Woman getting shunned from that fancy store on Rodeo Drive. Of course, it was a great movie. But you probably wouldn’t consider copying Julia’s pre-Edward look. Well, times have changed! Thigh-high boots are still sexy, but they are not regarded as inappropriate anymore.

Generally, thigh-high boots are great for nightclubs and bars. Yet, they can look fabulous for a casual trip running errands. You just need the right size boots, such as tall, petite, or wide calf.

Of course, too-tight boots can be unflattering and create a “muffin top.” To learn more about sizing, check out our article “How To Stretch Thigh High Boots – With A Few Methods To Try!

Can you wear thigh-high boots to a wedding?

Yes, you can wear thigh-high boots to a wedding. As long as the outfit does not look too casual, then you are good to go! A cute dress with thigh-high boots is especially cute to wear to an outdoor wedding.

A beautiful woman wearing a denim jacket dress and thigh high boots

Here is a gorgeous short floral dress paired with a wide-brim black hat and black thigh-high boots. This outfit would look great in a country-themed outdoor wedding. However, instead of a jean jacket, opt for a blazer. But keep it waist-length, like the one above. And choose a solid color, like navy, black, or red.

Here is a subtle and simple red wine blazer that comes in multiple colors. Click here to see it on Amazon. 

Here is another great floral dress with thigh-high boots to wear to a wedding. The cute, tiny pink flowers stand out beautifully against the white background. This outfit would look great for an outdoor or indoor wedding, as it is comfortable yet sophisticated! It could even be a great casual look for the summer, but we’ll talk more about that later.

Can you wear thigh-high boots to work?

Well, the answer is yes and no. Yes, you can wear thigh-high boots to work if it appears appropriate. Of course, the main factor for this outfit is not to show too much skin. It might be best to wear pantyhose to cover any skin. And choose a dress that is at least mid-thigh length.

You don’t have to be a model to look this good at work! A simple white sweater dress looks business-like when paired with a pinstriped suit jacket, like this one. Pantyhose with black thigh-high boots complete the outfit.

Any plain black dress would look outstanding with this long, sleek gray coat and bold, black thigh-high boots. This woman looks trendy and ready for business. Just remember to wear pantyhose to make them work-appropriate.

Do you wear socks with thigh-high boots?

Yes, it’s important to wear socks with thigh-high boots. Check out the reasons here:

  • More comfortable
  • More hygienic
  • Safer

Firstly, it’s more comfortable to wear socks with thigh-high boots. Pressure from the sides of the boots might create bruises or blisters without socks to protect the skin. You can’t walk on a blister without pain!

Secondly, it’s more hygienic to wear socks with thigh-high boots. Your skin has natural oils and bacteria. In particular, the feet have 125,000 sweat glands. The oil, bacteria, and sweat will transfer to the boot if you wear the boots without socks. This is what creates the bad smell in your gym shoes!

Thirdly, it’s safer to wear socks with thigh-high boots. You’re more likely to slip and fall in your boots if you don’t wear socks because your toes and feet have nothing to grip. So, avoid the embarrassment and pain and wear socks!

By the way, the socks do not have to cover the entire length of the boots; they should be at least calf height. If you’re wearing pantyhose with thigh-high boots, then you don’t want the socks to be thigh-high. But you should still wear socks over the pantyhose for comfort. No one will see them, so it’s okay!

If you’re not sure what kind of socks to wear with your thigh-high boots, then you should check out our helpful article “What Socks To Wear With Thigh-High Boots.”

How do I make my thigh-high boots not fall?

Black thigh high boots worn by a woman

Some boots have laces to tighten them, so they don’t fall. But most thigh-high boots don’t have laces. You have a few other options, though:

  • Use fashion glue
  • Wear thick socks
  • Use bootstraps
  • Apply double-sided tape

Can I wear thigh-high boots in summer?

Although it is not as common, you can wear thigh-high boots in the summer. In the heat, it would be best to wear a sleeveless dress or a dress with loose sleeves, especially since thigh-high boots tend to trap more heat. Remember to wear socks with them!

A beautiful red head woman wearing a white dress and black thigh high boots

Here is a gorgeous, white summer dress with a gold and white belt. This woman looks comfortable in the black thigh-high boots. Notice how the boots do not have a high heel. Thus, you can walk in the grass in them.

Here is a similar pair of low-heeled thigh-high boots. Click here to see it on Amazon.

This floral dress looks airy and cool with off-the-shoulder sleeves. It would be pretty comfortable to wear on a breezy day in the summer. And the brown boots look fantastic!

Here is a great pair of brown suede thigh-high boots. The chunky heels look chic. Click here to see it on Amazon. 

Short, loose sleeves would work great, too. This square-patterned, white dress looks loose and comfortable with the thigh-high black boots. Also, the white cloth belt gives the waist great definition and highlights her curves.

In Closing

Hopefully, this article gave you some inspiration for dressing in thigh-high boots. There are several different outfits to choose from. Just make sure to choose complementing or matching colors for the dress and thigh-high boots. And have fun shopping!

Leave a Reply