How to Wear Over The Knee Boots Over 50 Women?

As a woman over 50, I understand that navigating the fashion world comes with unique challenges. As our bodies change, so do our fashion needs. That said, I found a few select clothing essentials in my wardrobe. One of those items is a quality pair of over-the-knee boots.

Not only do they look stylish, but they can give any ensemble an extra boost of confidence. In this blog post, I will share my top tips for wearing over-the-knee boots for women over 50.

Also Read: What to Wear to Rock Concerts Over 50?

15 Outfit Ideas about How to Wear Over Knee Boots Over 50 Women

As a woman over 50, fashion knows no age limit. It’s all about finding stylish and age-appropriate ways to express our style. A pair of over-the-knee boots is one trendy item that can add a touch of sophistication and flair to any outfit. In this section, I will share 15 outfit ideas on how to wear over-the-knee boots for mature women.

1. Timeless and Polished

To create chic and elegant over-the-knee boot outfits for women over 50, begin with black skinny jeans that elongate your legs and flatter your figure. These versatile bottoms serve as the perfect foundation for a stylish ensemble. Layer a tailored blazer over a crisp white shirt for a timeless and polished look.

2. Cozy and Fashionable

On days when I want both comfort and style, I opt for a cosy sweater dress that hits just above the knee. Pairing it with my over-the-knee boots creates a chic and fashionable outfit. I often choose a pair of suede boots to add texture and depth to the overall look.

How to Wear Over The Knee Boots Over 50 Women

3. Casual and Put-Together

To discover stylish ways to rock over-the-knee boots after 50, try the classic technique of tucking jeans into your boots for a casual yet put-together ensemble. Opt for jeans in a dark wash as they have a slimming effect and create a flattering silhouette.

To elevate the overall look, incorporate a stylish blouse and add a statement belt for an extra flair. This outfit can be complemented with any boots, but over-the-knee boots, in particular, add a dose of sophistication and make a stylish statement.

Also Read: How to Wear Cowboy Boots After 50?

4. Edgy and Stylish

I combine a leather skirt with a chunky knit sweater for an edgy and stylish outfit. I wear opaque tights and slip on my over-the-knee boots to keep warm and create a cohesive look. This ensemble is perfect for those who want to embrace a trendier fashion style.

A pair of black boots with a slight heel can add a touch of elegance to this outfit.

How to Wear Over The Knee Boots Over 50 Women

5. Over-the-knee Boots with a Long Tunic

Number 5 on my list is wearing over-the-knee boots with a long tunic or oversized sweater tucked into leggings. This classic look showcases your legs and adds drama to fall and winter outfits. Oprah Winfrey often wears this style, pairing different sweaters and tunics with black leggings and over-the-knee boots for a polished and stylish appearance.

To recreate her look, choose a long sweater or tunic, add a leather jacket if possible, and opt for leggings that extend beyond the boots.

Chic over the knee boot outfits for women over 50

6. Relaxed Bohemian Vibes

If you have a bohemian spirit, why not embrace a bohemian style by pairing a flowy floral dress with your over-the-knee boots? I love layering on a denim jacket or a long cardigan for added warmth and style. Opt for boots with a slight heel to create an elongating effect and add a touch of elegance. Read our guide about- Bohemian Clothes for older Women.

7. Sleek Monochromatic Look

One foolproof way to create an elegant and elongating effect is by wearing all-black. I combine black leggings or skinny jeans with a black turtleneck sweater and top it off with my over-the-knee boots. This sleek monochromatic look is sophisticated and perfect for any occasion.

I often choose black leather boots with a slim silhouette to complete this ensemble.

Stylish ways to rock over the knee boots after 50

8. Sophisticated and Chic

To stylishly wear over-the-knee boots after 50, consider selecting a knee-length skirt in a complementary color to your boots. This combination creates a sophisticated and put-together look that exudes timeless elegance.

Pair the skirt with a blouse or a button-down shirt for a polished appearance. Layer on a blazer or a structured jacket to add an extra touch of refinement. This ensemble is perfect for occasions such as business meetings or special events where a chic and professional look is desired.

Regarding footwear, opt for suede boots to introduce a luxurious touch to the ensemble. You can feel cool wearing over-the-knee boots when you include these things in your outfit.

Stylish ways to rock over the knee boots after 50

9. Flattering Wrap Dress

Wrap dresses are universally flattering and look great with over-the-knee boots. Opt for a wrap dress in a flattering print or solid color, and wear it with your boots. To define your waist, cinch it with a belt.

This outfit is effortlessly chic and suitable for a dinner date or a social gathering. For footwear, a pair of suede boots with a pointed toe can add a touch of sophistication.

Also Read: How to Wear Sneakers over 50 Women?

10. Feminine and Stylish

Number 10 on my top 15 outfit ideas for women over 50 Pair over-the-knee boots with a flowy midi skirt and a tucked-in blouse. This classic and chic look exudes elegance. Choose a lightweight, flowy midi skirt in your preferred color.

Tuck in your blouse and accentuate your waist with a belt or waist tie. Opt for low-heeled, stylish over-the-knee boots. Add an oversized knitted sweater or cropped jacket for extra style and comfort. It’s a fashionable and mature way to wear over-the-knee boots.

Stylish ways to rock over the knee boots after 50

11. Effortless Jumpsuit

Jumpsuits are versatile and trendy, making them a great option for mature women. Choose a tailored jumpsuit and wear it with your over-the-knee boots for a chic and effortless ensemble. Layer with a blazer or a cardigan for added sophistication. Opt for boots with a sleek silhouette to balance out the overall look.

Also Read: How To Wear Doc Martens Over 50 Women?

12. Statement Coat and Boots

When the weather calls for a statement coat, why not pair it with your over-the-knee boots? Choose a faux fur or a tailored wool coat as your outerwear and let it be the focal point of your outfit. Keep the rest of your outfit simple, and let the coat and boots take center stage.

Depending on the coat style, you can opt for boots in a neutral color or match the coat’s color for a coordinated look.

outfit with over the knee boots as a mature woman

13. Playful Patterns

When it comes to knowing how to wear over-the-knee boots over 50, a great option is to add a playful touch to your outfit by selecting a patterned dress or skirt. Pair it with solid-colored tights and your boots to create a fashionable ensemble. You can choose a pattern that suits your style, whether it’s a floral, geometric, or animal print.

This combination allows you to express your creativity while maintaining a chic, age-appropriate look. This outfit is particularly well-suited for a day out or a casual gathering where you want to showcase your fashion-forward sense. Regarding footwear, ensure that the boots you choose complement the colors present in your dress or skirt.

Over the knee boot styling tips for women in their 50s and beyond

14. Chunky Knit and Mini Skirt

If you’re a fan of layering, consider combining a chunky knit sweater with a mini skirt or shorts. Pair them with your boots for a stylish and slightly unconventional look. You can add tights if desired for extra warmth and style. Opt for boots with chunky heels or a rugged sole to complete this fashion-forward ensemble.

15. Rock-Inspired Boldness

The last outfit idea on my list is a personal favorite a black leather jacket, black leggings, a graphic band tee, and over-the-knee boots. This timeless look is perfect for women over fifty and versatile for different occasions.

The leather jacket adds warmth and style, while the graphic tee adds a rock ‘n’ roll touch. The black leggings for women over 50 contrast the jacket, and the boots elongate the silhouette. It’s a bold yet classic combination, mixing timeless pieces with contemporary fashion.

Styling over the knee boots for women over 50

Tips for Enhancing the Look with Over-the-Knee Boots

Age should never hinder personal style. Over-the-knee boots, a trend I adore, elevate outfits effortlessly, boosting confidence and chicness. Here are tips tailored to mature women.

  • Prioritize comfort by choosing over-the-knee boots with a low or chunky heel.
  • Opt for a length that flatters your body shape and height, such as just above the knee or mid-thigh.
  • Stick to classic colors like black, brown, or grey for a timeless and versatile look.
  • Experiment with layering by adding a long coat or chunky sweater to create depth and dimension.
  • Keep accessories minimal and elegant to complement your outfit without overwhelming it.
  • Stay true to your personal style and wear over-the-knee boots with confidence.


Can I wear over-the-knee boots to a job interview?

As a mature woman, avoiding wearing over-the-knee boots to a job interview is best. Opt for conservative footwear that aligns with professional standards. Choose closed-toe shoes with moderate heels or flats. Dressing appropriately demonstrates professionalism and respect for the company.

Is it still fashionable to wear boots over jeans?

As an older woman, I can confidently say that wearing boots over jeans can still be fashionable. It’s a versatile and stylish look that can be adapted to suit different occasions. Over-the-knee boots add a touch of sophistication and elevate the outfit. Ensure the overall ensemble is well put together and suits your style. Embrace the trend with confidence and embrace your unique fashion choices.

Are over-the-knee boots suitable for all body types?

Over-the-knee boots can be suitable for all body types, including older women. Consider comfort and practicality when choosing a pair. Look for lower heels and wider calf sizes. Styling also plays a role—pair them with above-the-knee skirts for balance or leggings for a modern look. Find what works best for your body shape and personal style.

Can shorter women pull off over-the-knee boots?

Yes, shorter women can pull off over-the-knee boots. Choose boots with a shorter shaft and moderate heel height. Pair them with shorter skirts or leggings to create a lengthening effect. Find the right balance and wear what makes you feel confident.


Having the right outfit can help you look amazing at any age. Over-the-knee boots for women over 50 are a great addition to your wardrobe and can be styled in many ways. From casual jeans and a top to office-ready ensembles to glamorous dresses, over-the-knee boots make a statement and add style and sophistication to any look. With the many different styles available, you will surely find a pair you love. Try out one of the 15 ideas above, and you’ll be sure to make a fashionable statement!

Leave a Reply