How to Wear Thigh High Boots Over 40 (Without Looking Trashy)

Let’s talk about one of my favorite trends of the season: thigh high boots!

Yes, you’re probably curious about how to wear thigh high boots over 40 or even if you should want a pair at all.

But here’s the thing, thigh high boots aren’t just for younger women or celebrities. They’re for us, too!

Thigh-high boots are a fantastic way to add drama and flair to your outfits.

Not only do they keep you warm, but they also make your legs look longer and boost your confidence.

But I know what you’re thinking. “How do I wear them without looking like I’m trying too hard?”

Don’t worry, I’ve got you!

I’ll share some tips and tricks on how to stylishly wear thigh-high boots when you’re over 40, without looking trashy.

How to wear thigh high boots over 40: Choose the right boots

When shopping for thigh-high boots, the first thing you should do is find the fit and style that work for you.

Not all boots are the same, so it’s important to choose a pair that flatters your legs and suits your taste.

Here are three things to consider when choosing your boots:

#1 Not too tight, not too loose

Avoid boots that are too tight, too loose, or too slouchy, as they can make your legs appear shorter or wider than they actually are.

Opt for boots that fit snugly around your calves and thighs, but not so much that they restrict circulation or create bulges.

#2 Height

When choosing boots, consider the heel height, toe shape, and material.

For instance, a low or medium heel can offer more comfort and a flattering look compared to a high heel.

A pointed toe can help elongate your legs, while suede or leather can add texture and warmth to your outfit.

#3 Don’t be afraid of colors or patterns

Don’t be afraid to experiment with different colors and patterns!

You can go for classic black or brown, or spice things up with red, burgundy, navy, or even animal print. Just make sure they match your outfit and reflect your personality.

Here are some examples of different styles of thigh high boots and how to wear them:

If you’re aiming for a sleek and sophisticated look, opt for a pair of black leather thigh-high boots with a pointed toe and a stiletto heel.

Wear them with a black leather dress or a black pencil skirt, along with a blouse, for a chic and sexy outfit.

For a cozy and casual look, consider choosing a pair of brown suede thigh-high boots with a round toe and a low heel.

Pair them with a beige sweater dress or a denim shirt dress to create an adorable and comfortable outfit.

If you’re looking for a fun and edgy look, consider opting for a pair of leopard print thigh-high boots with a square toe and a chunky heel.

Pair them with a black leather skirt or leggings and a graphic tee for a cool and trendy outfit.outfit.

Strike the right balance of sexiness

Thigh-high boots are undeniably sexy!

They have the amazing ability to effortlessly captivate attention and highlight your legs, making you feel like an absolute powerhouse of confidence and allure.

Who says you can’t look sexy and classy at the same time?

When you rock those amazing boots, all you need is to strike the perfect balance.

Style them with tasteful pieces to create a stunning ensemble that will turn heads for all the right reasons!

Don’t worry about looking trashy or inappropriate – you’ve got this!

Here are some things to consider when choosing your clothes:

#1 Higher neckline

If you want to limit the amount of skin you’re showing, consider choosing clothes that provide partial coverage, such as tops or dresses with high necklines or midi/maxi lengths.

This way, you can maintain a sophisticated look without going overboard.

#2 The right hemline

When youre wearing thigh high boots you want to choose a hemline that covers the top of your boots or a few inches higher.

Midi lengths can be your go to lengths when wearing thigh-high boots.

This creates a sleek and seamless look that elongates your legs while showing just a hint of skin.

Although, mini skirts work really well with thigh high boots too!

#3 Add layers

Drape a coat over your shoulder for an incredibly bold look!

Not only does a coat add warmth if it gets cold, but it also adds structure, and a bit of elegance to your outfit, and also helps you seamlessly transition from day to night or from casual to formal.

Here are some examples of various clothing items and how to style them with thigh-high boots:

If you’re aiming for a feminine and flirty look, opt for a floral midi dress with a high neckline and long sleeves. To add a contrasting touch and a pop of color, style it with black suede thigh-high boots.

If you’re aiming for a modern and minimal look, opt for a monochrome outfit featuring a white shirt dress and white leather thigh-high boots. To add some interest and texture, accessorize with items like a belt, a hat, or a bag.

If you’re aiming for a classic and cozy look, opt for a sweater dress in a neutral color such as beige, gray, or navy. Complete the outfit with brown leather thigh-high boots for a warm and comfortable ensemble.

Mix and match

Thigh-high boots are a statement piece that can instantly elevate any outfit.

To take your style to the next level, try mixing and matching different colors, prints, and textures. This will create a striking contrast and add interest to your overall look.

Here are some things to consider when choosing your colors, prints, and textures:

#1 Don’t be afraid to try colors and prints

Don’t hesitate to explore various combinations of colors, prints, and textures when styling thigh-high boots if you’re over 40.

By mixing neutrals with vibrant pops of color, pairing animal prints with solids, or combining leather with knitwear, you can create fun and chic outfits.

You can also use the color wheel to find complementary or analogous colors that work well together.

#2 Rule of three

Balance your outfit using the rule of three. This means incorporating no more than three colors, prints, or textures in your ensemble. For instance, you could style a black leather skirt with a white sweater and brown suede boots.

#3 Accessorize

Accessorize to bring your outfit together! For instance, you can elevate your look by adding a scarf, hat, or bag that complements the colors or prints in your boots or clothes.

Here are some examples of different combinations of colors, prints, and textures and how to wear them with thigh high boots:

For a vibrant and playful look, opt for a pair of red leather thigh-high boots with a pointed toe and a medium heel.

Style them with a green plaid midi skirt and a white button-down shirt to create a striking contrast and add a pop of color.

For a sophisticated and elegant look, opt for a pair of black suede thigh-high boots with a round toe and a low heel. Wear them with a gray knit midi dress and a black coat for a cozy and classy outfit.

If you’re looking for a trendy and edgy look, consider opting for a pair of metallic gold thigh-high boots with a square toe and a chunky heel.

Wear them with a black leather mini skirt and a graphic tee for a cool and flashy outfit.

Accessories

Accessories can make or break your outfit, so choose them wisely, especially when wearing thigh-high boots.

You don’t want to overdo it or clash with your boots, but at the same time, you don’t want to look too plain or boring.

Consider this:

Use accessories to define your waistline, keep you warm, add some color or sparkle, and carry your essentials.

Which could look like wearing a wide belt over a shirt dress and boots, a floppy hat with a sweater dress and boots, a plaid scarf with a coat and boots, or a statement necklace with a leather dress and boots.

Use accessories to create harmony or contrast in your outfit.

For example, you can match your accessories with your boots or clothes, or you can mix different colors, prints, or textures to add interest and fun.

Use accessories to express your style and personality

Accessories are a fantastic way to express your unique style and personality.

For instance, you can add a touch of elegance with a brooch, pendant, or charm that holds a special meaning to you.

Alternatively, you can showcase your hobbies or passions with a quirky or unique accessory.

Let your accessories be a reflection of who you are!

Here are some examples of different accessories and how to wear them with thigh high boots:

For a boho and romantic look, opt for a pair of brown leather thigh-high boots with a round toe and a low heel then wear it with a floral midi dress and a denim jacket.

Complete the look with a floppy hat, a fringe bag, and some hoop earrings.

For a glamorous and chic look, opt for a pair of black leather thigh-high boots with a pointed toe and a stiletto heel.

Pair them with a black leather dress and a faux fur coat. Complete the outfit with a pearl necklace, a clutch bag, and some sunglasses.

You’ll be sure to turn heads!

And if you’re aiming for a casual and sporty look, consider opting for a pair of white leather thigh-high boots featuring a square toe and chunky heel.

These can be paired effortlessly with a denim shirt dress and a bomber jacket. To complete the ensemble, accessorize with a baseball cap, a backpack, and some sneakers.

Frequently asked questions

Are thigh high boots appropriate for women over 40?

Absolutely! Thigh-high boots are suitable for women of all ages, and they’re incredibly fun to wear!

They effortlessly elevate your outfits, adding a touch of style and sex appeal.

There’s no reason why being over 40 should stop you from rocking thigh-high boots.

So if you were thinking about buying a pair – do it!

How do I keep my thigh high boots from falling down?

There are several tricks you can try to prevent your thigh-high boots from falling down.

The easiest option (and what I do) is to wear them with high socks, then they’re not going anywhere.

You can also wear them with, jeans, leggings or pants underneath for added support.

Another trick is to use double-sided tape, elastic bands, or boot straps to secure them in place.

You can also buy boots with a zipper, lace-up, or drawstring closure for added support. You can also look for boots that have some stretch or lacing to adjust to your legs.

If none of these work, you can always take your boots to a cobbler or a tailor to get them altered to fit you better.

How do I wear thigh high boots with dresses?

A great way to style thigh-high boots with dresses is by selecting a hemline that covers the top of your boots, like with a midi or maxi length.

Another option is to choose dresses with a slit or a button-down front, allowing you to proudly showcase your fabulous boots.

You can get creative by mixing and matching different colors, prints, and textures to add contrast and interest to your outfit.

For instance, try wearing a flared floral midi dress with brown leather boots, a black leather dress with black suede boots, or a gray knit dress with metallic gold boots (now that’s bold!).

The possibilities are endless!

How do I wear thigh high boots if I’m short?

A good way to wear thigh-high boots if you’re short is by choosing boots that have a pointed toe and a heel to elongate your legs.

You can also wear monochromatic outfits to create a seamless look. You can also avoid wearing skirts or dresses that are too long or too short, as they can make your legs look shorter or wider than they are.

For example, you can wear a black leather skirt with black leather boots, a white shirt dress with white leather boots, or a denim shirt dress with brown suede boots.

Subscribe to my newsletter

And that’s it! I hope you enjoyed this article and learned some tips and tricks on how to wear thigh high boots over 40 without looking trashy.

As you can see, thigh high boots arent only sexy and stylish, but also versatile.

You can wear them with any outfit and for any occasion, as long as you follow these simple rules: choose the right fit and style, balance the sexiness with modesty, mix and match colors and prints, and accessorize smartly.

And if you loved this, please share with a friend who would love it too!

And don’t forget to subscribe for more fashion tips and inspiration.