How To Style Thigh High Boots (Classy And Casual Outfit Ideas)

There are few statement pieces that make a statement quite as loudly as the thigh high boot. This single piece of clothing can make or break an outfit.

Throw on a pair of thigh high boots, and your jeans-and-a-cute-top instantly has a touch of Parisian chic. But add thigh highs to your sparkly mini, and you just might be bordering on trashy.

How To Style Thigh High Boots (Classy And Casual Outfit Ideas)

Thigh high boots are an item all fashionistas drool over. There’s just something about the long lines and casual cool that make thigh high boots always desirable.

But getting them right can be complicated, and many of us who aren’t quite model proportioned worry that we just can’t pull them off.

With this guide, you don’t have to worry anymore. We have all the tips and tricks you need to style your thigh high boots for every occasion. So, you can wear your boots to work, right through to lunch, and for drinks afterwards.

Yes, thigh high boots are just that versatile! Read on to find out why you need a pair of thigh high boots in your life.

Basic Tips For Dressing Your Thigh High Boots

Basic Tips For Dressing Your Thigh High Boots

Once you’ve bought your first pair of thigh high boots, you probably have lots of ideas to style them. Only when you start to experiment with outfits, you find nothing quite looks right.

Rather than adding an effortless sexiness, these boots just look trashy.

Or maybe you bought yourself a pair of over the knee, or OTK, boots, and find you just don’t know how to style them. The boots themselves are fab, you just can’t decide on an outfit that works.

No matter what your dilemma is, we’re here to help. These are a few basic styling tips to remember when you want to wear your thigh high boots.

  • Remember that the boots are sexy anyway. There’s just something about a pair of thigh high boots that’s innately sexy. The way they draw the eye to the leg, the length they add, and the unforgettable Pretty Woman connection.

    With that in mind, you don’t need to do much to make your thigh high outfit sexy. So, rather than styling your boots with crop tops and tight shirts, look for looser cuts. 
  • Balance lengths. Consider the overall look of the outfit, and where each layer falls. Pairing your thigh high boots with a long coat and a short skirt keeps the look fresh and casual. Avoid skirts that are too short.

    A mini can look cute, but try to keep the amount of thigh on show at 5 inches maximum. And if you’re going for a short skirt, avoid a crop top.
  • Stick to classic materials. This goes for both how you style the shoe, and the shoe itself. Shiny vinyl OTK boots look fantastic on the runway, and trashy in reality. Suede and soft leathers are much easier to wear.

    Plus, the naturally supple materials fit the legs better. Style your boots with wool and cotton, to soften the sexy look. 
  • Simplify your colors. The best thigh high boots are neutral shades such as black, gray, or tan. Anything else can be a bit too eye-catching, especially for everyday wear. And the same goes for the rest of your clothes.

    Don’t shy away from color, but avoid bright and vivid shades until you know your boots better.
  • Think of them as a finishing touch. Thigh high boots over a pair of jeans is a classic, and it works almost every time. Rather than styling an outfit around your boots, think of how you can use the boots to finish a casual look. 
  • Get the right pair of boots. Okay, this is probably the first tip you need to know, but you absolutely have to make sure your boots fit right. Thigh high boots need to be molded to your legs, and fit like a pair of gloves.

    Don’t just buy the first pair that catches your eye. Try a range of materials and shades until you find the right pair for you.

When Can You Wear Thigh High Boots?

When Can You Wear Thigh High Boots

Thigh high boots are a surprisingly adaptable piece of clothing. Styled correctly, a pair of thigh high boots can work for a casual brunch, a day at the office, an evening meal, and a night out. They’re really versatile, they just need to be styled with some care.

Jeans and leggings are classic thigh high combinations, because they let the boots do all the talking. Short skirts and mini dresses also work well, with layers showing the boots (and your legs) at their very best.

And even knee-length and midi dresses can be given a chic edge with over the knee boots.

Although we hesitate to say there are some things you definitely shouldn’t wear your boots with, we do have some tips on what to avoid. 

Flashy clothing, too many bright colors, and dazzling fabrics can look way too much when styled with thigh high boots. The boots are a statement all by themselves. The rest of the outfit should step back and let them do the talking.

The Easiest Way To Wear Thigh High Boots

The Easiest Way To Wear Thigh High Boots

When you go shopping for your thigh high boots, there’s one other piece of clothing you should pick up: a statement coat. The statement coat and thigh high boots are the perfect combination, and the kind of outfit you see all over street style blogs.

Long coats should be a staple piece in every fashion-lover’s wardrobe. Whether it’s a mini or a maxi, the right long coat can instantly create an outfit. And they go so well with thigh high boots, you’ll never worry about what you’re wearing again.

Okay, that’s not a guarantee we can make. But on days when you really don’t know what to wear, thigh high boots plus statement coat equals effortless style. The rest of the outfit hardly matters at that point.

Consider the silhouette when you come to choose your coat. Sleek boots can be matched with a voluminous coat, or a coat with sharp edges.

Once you’ve nailed your silhouette, move on to colors. Picture how the boots and coat work together. If you’ve gone for plain boots, you might consider a coat with a bolder pattern. Or if your boots are a sultry black, consider a softer neutral for the coat.

Before You Wear Thigh High Boots

Before You Wear Thigh High Boots

By now, you should have a pretty decent idea of the basics of how to wear thigh high boots (without looking trashy). But before we dive into your wardrobe to put together some outfits, here are some basic rules to remember:

  • DO let the boots do the talking. These are a bold outfit choice, and should be the focal point of the outfit.
  • DON’T try to make it sexy. The boots do all the work by themselves, anything too flashy will just look trashy.
  • DO invest in a statement coat. Thigh high boots and a statement coat will solve your outfit woes.
  • DON’T buy the first pair of OTK boots you see. Take the time to find the pair that fit you right.
  • DO think about layers and levels. It’s all about balance with a pair of thigh high boots. Keep a part covered – arms, neck, legs, etc.
  • DON’T overdo colors. Unless you’re careful, the colors will only detract from your incredible thigh high boots.

Styling Casual Outfits With Thigh High Boots

Styling Casual Outfits With Thigh High Boots

Leggings and skinny jeans are the natural thing to wear with thigh high boots. The close-fitting clothing fits underneath the skin tight boots, giving you a daytime look that’s effortless and stylish.

If you’ve been putting off buying a pair of thigh high boots because you think they’re only for evening wear, then you need to rethink.

Thigh high boots in the day don’t seem trashy, not if you’ve styled them right. Instead, they add a fashion finish to even the simplest of outfits. Aka the jeans and a top look that we all default to when we can’t be bothered.

Skinny jeans, thigh high boots, and a slouchy sweater are also an easy way to do daytime fashion. The soft sweater tones down the thigh high boots, and gives them a twist of the casual.

Denim works really well with black and brown boots, and black jeans can also work for a monochrome look. Tan and gray boots are also versatile, although avoid jeans that are too dark. Otherwise, the eye will look straight past the boot, and go to the thigh.

One final piece of advice for casual outfits — they have to be skinny jeans! Nothing else will fit right in your tight thigh high boots.

Brunch Casual

Add a twist to the classic brunch look by pairing your sweater and shirt look with some thigh high boots and your favorite jeans. Avoid volume from oversized knits, and instead keep a sleek silhouette with a bold colored sweater.

Cropped sweaters can work well, or tuck the front in to neaten the line.

For Shopping Trips

Flat thigh high boots are ideal for days when you plan on a lot of walking. Combine your boots with an oversized t-shirt, or some loose fitting knitwear (depending on the weather).

You’ll have plenty of room for movement when shopping heats up, but the boots add a sophisticated finish. 

Bar Hopping

Heading out for drinks with friends after work? Use a pair of thigh high boots with jeans and a top to make it look like you’ve made an effort (even if you really don’t have the time).

Keep the upper half streamlined, a tailored top or sleek t-shirt works, and top the look off with a leather jacket.

Winter Walks

When fall sets in, thigh high boots become an outfit savior. Grab your favorite statement coat, and a chunky scarf. Grays and tans are the perfect colors for icy days. 

Styling Work Outfits With Thigh High Boots

Styling Work Outfits With Thigh High Boots

Yes, you can wear a pair of thigh high boots to the office. You just have to find the right outfit for them!

We have two top tips for wearing your thigh high boots to work.

First, break out the blazer. A blazer goes really well with an over the knee boot, because the harsh lines balance the sleek finish of the boots. Choose a blazer with dark colors, or a simple print.

Longline blazers are incredibly chic, and regularly turn up on the runway. Keep the rest of your outfit simple if you’re using a long blazer, so the blazer and boots balance each other out. 

Shorter blazers have a little more room for fun, so maybe mix it up with a bolder shirt. Wear your blazer with pants, or jeans, if your workplace allows.

Second, use length. A pencil midi dress or skirt will add class to any thigh high boots. Keep the patterns and colors toned down (you’re in the office, after all). If you fancy trying something fun, look for an asymmetric hemline.

How seamlessly you can add thigh high boots to your work outfit will depend on your workplace. And if you’ve bought a pair of hot pink vinyl thigh high boots, then they’re never going to be work appropriate.

Black, gray, or tan boots? You might have a new office-outfit staple. 

Styling A Night Out Look With Thigh High Boots

When it comes to dressing your thigh high boots for a night out, things do get a little tricky. Thigh high boots are sexy, and finding a going outfit that doesn’t veer into trashy can take some effort.

That mini that looked so cute with heels might look a little too Pretty Woman with thigh high boots.

But that doesn’t mean it can’t be done! And once you’ve mastered the basic looks, you can start to experiment more with your boots.

Planning on heading to the club? Then go for a classic — the little black dress. With black boots, the LBD is young and fun. Keep things classy by choosing an LBD with sleeves.

That way, you can keep the length shorter, without showing more skin than you want. Long, fitted sleeves match the boots, and balance out a simple dress.

Or look for shorter sleeves with volume. If you’re worried about throwing off the balance, look for voluminous minis with open backs or cut out designs.

And it doesn’t have to be black! Rich tones and jewel colors can work just as well. But avoid anything too bright — it will clash with the sophisticated boot.

Think about fabrics as well. Natural materials such as leather and suede go well with thigh high boots, as do feminine fabrics such as lace and silk.

For a special occasion, consider the midi dress (or skirt). Asymmetric hems and long slits can take these outfits from dinner to the club, while your boots remain the star of the show. A wrap dress is another good choice as well. The slouchy finish contrasts the sleek boots. 

With a little more coverage, you can play around with colors and materials as well. A silk wrap dress or leather pencil skirt can add an extra touch of luxury to an outfit for a special occasion.

(And if sometimes you look a little trashy, then that’s the fun of a night out!)

Styling Dresses With Thigh High Boots

Styling Dresses With Thigh High Boots

As much as we love jeans and thigh high boots, we love dresses and thigh high boots even more. In fall and winter, thigh high boots can be used in place of tights. They keep you warm, and they can turn a plain dress into a high-fashion outfit.

Most dresses can look good with thigh high boots, particularly if you style them right. But, there are some things to stay away from. Yes, we’re talking hemlines.

A very short mini with a pair of thigh high boots can look amazing, but it’s a fine line between classy and trashy. As a general rule, the amount of thigh on show should be around 3 inches, and no more than 5 inches. 

If you do plan on going shorter, then you have to balance it out with more fabric on top. Long sleeves and a high neckline can add some sophistication back to the outfit.

Volume is another way to navigate a short hemline. This can balance out the sleek silhouette of a pair of OTK boots, and the extra fabric distracts from just how much thigh is on show.

Midi and maxi dresses are nearly always good with a thigh high boot. Look for dresses with cut-outs and leg slits if you want to make sure your boots are on show. 

Again, don’t forget to consider materials. A cozy sweater vest can lose a few inches of the hemline thanks to a chunkier fabric. But if you’re wearing clinging silk, you might want to consider a midi dress to balance things out. 

Once you’ve nailed the thigh high boot and dress combo, your fall dressing is sorted.

Patterns, Monochromes, And Thigh High Boots

The most popular color for thigh high boots tends to be a classic black, but neutrals are also common. The advantage to these types of boots is their versatility.

These colors are simple to dress up and down, and are unlikely to clash with whatever outfit you have planned.

But fashion isn’t just about easy dressing. Experimenting with color and pattern is one of the reasons so many of us love to dress up. So, who says over the knee boots can’t be fun?

Patterned boots are getting more and more popular, and many retailers have jumped on the trend.

If you want to try a more exciting thigh high, we recommend starting with animal print. Snakeskin or crocodile tend to use muted colors with subtle patterning — perfect for experimentation, without being too bold.

Want footwear that makes a statement? Look for jewel toned boots, or a shiny vinyl finish. Yes, they’re harder to style, but the end result is so worth it.

Do You Have To Be Tall To Wear Thigh High Boots?

Do You Have To Be Tall To Wear Thigh High Boots

Thigh high boots tend to be associated with long legs, but that doesn’t mean petite ladies can’t make them work. 

So, here are some tips for how to wear thigh high boots if you’re on the short side.

It’s All About Fit

This is true no matter your height, but thigh high boots have to fit impeccably when you’re short. Thigh high boots with a slouchy fit can look uncomfortably like dress up even on taller girls, so when you’re petite you have to be extra careful.

Find boots that fit like a glove, and they’ll work to elongate your legs.

Be Careful With Hemlines

Thigh high boots on petite girls typically finish further up the leg. This can make hemlines difficult. A standard mini will often overlap the boot, or leave only the slightest peek of skin.

This has a shortening effect. But when you wear a shorter dress, things start to look trashy. 

Tuck In Your Tops

Jeans and thigh high boots are pretty easy to style on petite girls, and follow the same standard rules. But one additional piece of advice is to tuck your shirt, sweater, t-shirt etc. into your jeans.

It shows off the line of the tight boots and jeans, and creates a sleek silhouette.

The most important tip for all women looking to style thigh high boots is: make sure you’re comfortable. Thigh high boots can be an intimidating piece of footwear, and we’re sure you look fantastic in them.

But they need to be worn with confidence!

Before you start planning your outfit, make sure you have the best thigh high boots for you. The right pair will make you feel, and look, incredible.

Frequently Asked Questions

Do Thigh High Boots Make You Look Trashy?

No, thigh high boots don’t make you look trashy. Styled right, a pair of thigh high boots can look classy and stylish, and add the finishing touch to your street style. 

How Do You Wear Thigh High Boots?

Thigh high boots can be worn for a casual look when paired with jeans, or for a night out with the right dress. They’re a surprisingly versatile piece of footwear!

Keep the rest of your outfit simple, balance the sleek line of the boots with volume elsewhere, and avoid hemlines that show more than 5 inches of thigh. With these basic rules mastered, you’ll soon find your thigh high boots become your go-to shoe.

Do Thigh High Boots Suit Everyone?

Thigh high boots can suit everyone, you just have to make sure you get the right pair. Fit is everything, and most people look better in thigh high boots that are molded to the skin.

If you have longer legs, you might enjoy experimenting with a slouchy fit. Once you’ve chosen the right boot, it’s easier to find an outfit to suit your proportions. Remember, a statement coat is always the best way to dress up thigh high boots. 

Miranda Cole
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