13 Outfit Ideas on How to Wear Ankle Boots for Women Over 50

What better way to add style to an outfit than with ankle boots? Regarding the fashion choices of those over 50, ankle boots are a great option to add sophistication and flair. With the right choice, you can look your best regardless of your wear or where you go. Here, I’ll show you some tips on wearing ankle boots over 50 – and help you ensure you always look your best.

How To Wear Ankle Boots Over 50?

As a fashion enthusiast in my fifties, age should never limit our style choices. One versatile footwear option that I adore is ankle boots. These stylish shoes can add a touch of sophistication and edge to any outfit. Today, I’m excited to share 13 outfit ideas on how to wear ankle boots for women over 50. Let’s dive in!

1. A Flowy Floral Maxi Dress and Brown Suede Ankle Boots

The first outfit is a flowy floral maxi dress with brown suede ankle boots, allowing me to express my personality while aging gracefully. The ankle boots provide stability, while the dress adds movement and lightness. The suede offers texture and warmth, making them comfortable to wear. Complete the look with a wide-brimmed hat and a long necklace for added style. Ideal for spring days and leisurely activities.

A Flowy Floral Maxi Dress and Brown Suede Ankle Boots, How To Wear Ankle Boots Over 50?

2. Ankle Boots with a Chunky Heel

Opt for dark-wash skinny jeans and an oversized sweater for a cozy, laid-back outfit. Pair them with ankle boots featuring chunky heels for a stylish look. Accessorize with a long pendant necklace and carry a crossbody bag for added functionality.

Also Read: How To Wear Jeans Over 50 Women?

Ankle Boots with a Chunky Heel as How To Wear Ankle Boots Over 50

3. Studded Ankle Boots with a Leather Jacket

An ankle boot with studs is a great way to give your outfit an edge. Paired with a leather biker jacket, this look can be fierce and timeless. Start with a pair of black leather ankle boots with geometric studs. They can be worn with skinnies, a T-shirt, tucked-in trousers, and a peplum top.

Opt for a warm-toned biker jacket with a slim fit to add a feminine touch to the look. Look out for pieces made from lightweight leather which can be easily folded away to fit into your handbag. Balance the rock-chic outfit with a delicate chain necklace and a classic purse. Top off the look with a pair of oversized aviator sunglasses.

Studded Ankle Boots with a Leather Jacket, ankle boots for women over 50

4. Sleek black Ankle boots with a Belted Blazer

Opt for a tailored sheath dress with a pair of sleek black ankle boots for a polished and professional appearance. Layer a belted blazer for a structured and refined look. Add a touch of elegance with pearl earrings and carry a structured tote bag.

Sleek black Ankle boots with a Belted Blazer as Stylish ankle boot outfits for women over 50

5. Tan suede Ankle Boots and a Denim Shirt Dress

Even as an older woman, I’ve never felt age should limit our style. Comfort and practicality are key, but so is looking stylish. I love a good pair of tan suede ankle boots, and it’s one of my go-to options for a cute, comfortable outfit.

Also Read: How to Wear Cowboy Boots After 50?

These days, I’m wearing my tan suede ankle boots with a denim shirt dress. I have a midi-length dress, which hits just below my knees. It’s made from thick, structured denim that holds its shape well, giving it a nice silhouette.

I tuck the shirt dress into my boots for the perfect look and leave it slightly undone. I complete the outfit with some earrings and a cute handbag. It’s a sharp, pulled-together look perfect for lunch with friends or running errands.

Tan suede Ankle Boots and a Denim Shirt Dress for Fashion tips for wearing ankle boots after 50

6. Flowy jewel-toned midi wrap dress and Velvet Ankle boots

Introducing one of my favorite looks I like to wear in autumn. This is it if you want something comfortable and stylish over 50. The flowy jewel-toned midi wrap dress is perfect for the autumn weather; pair it with some velvet ankle boots, and you have a classic outfit that never goes out of style. The colors of the dress go perfectly with the dark tones of the velvet, creating a coordinated look that will draw the right kind of attention.

Also Read: Combat Boots for Women Over 50

Flowy jewel-toned midi wrap dress and Velvet Ankle boots as Comfortable ways to wear ankle boots in your 50s

7. Pleated A-line Skirt and Ankle Boots with a Stacked Heel

For a sophisticated and chic outfit, pair a pleated A-line skirt with a turtleneck sweater. Next, elevate the look with ankle boots with a stacked heels. Finally, wrap a patterned scarf around your neck and carry a structured handbag for a polished finish.

Pleated A-line Skirt and Ankle Boots with a Stacked Heel as Ankle boot outfit ideas for mature women

8. Embroidered peasant dress with Ankle Boots

Some people may think the peasant dress is outdated and too boho. Not so! When styled correctly, a peasant dress with ankle boots can look stylish and on-trend while rocking a boho-chic vibe. The key to styling a peasant dress is picking one with embroidery – this dress was made for it! Choose a dress that hits your mid-calf and pair it with ankle boots with a larger heel to create an elongated frame.

Throw on some hoops and bangle bracelets, and you’ll be a timeless beauty. Plus, ivory pieces are great for transitioning from summer to fall so you can wear this stylish outfit all year long.

Embroidered peasant dress with Ankle Boots as Trendy ways to style ankle boots for women over 50

9. Black Ankle Boots with a Pointed Toe

For a sleek and sophisticated outfit, opt for a black turtleneck dress paired with black ankle boots featuring a pointed toe. Accessorize with silver hoop earrings for a touch of modernity. Carry a structured black handbag and finish off the look with a pop of red lipstick.

A Black Ankle Boots with a Pointed Toe as Stylish ankle boot outfits for women over 50

10. Chunky Platform Ankle Boots and a bomber jacket


For a classic look over 50, a pair of chunky platform ankle boots and a bomber jacket is a timeless combination. With this outfit, you can choose a neutral bomber for a low-key look or a bright, vibrant style for a more daring look. For the boots, you can go with a classic brown or black leather option for a classic look or a bold color and texture like animal print for a bolder look. Top off the look with a light scarf to add a splash of color, and you’ve got a classic look with a modern twist.

11. Brown Leather Ankle Boots and a Canvas Tote Bag

For a casual denim-inspired ensemble, choose a chambray shirt dress and pair it with brown leather ankle boots. Layered pendant necklaces will add a touch of femininity. Complete the look with oversized sunglasses and carry a canvas tote bag for a laid-back and effortless vibe.

Brown Leather Ankle Boots and a Canvas Tote Bag for Women over 50 outfit

12. Patent Leather Ankle boots with Black Dress

Opt for a tailored little black dress paired with patent leather ankle boots for an elegant, timeless outfit. Accessorize with pearl drop earrings for a touch of sophistication. Carry a satin clutch and finish the look with nude lipstick for a classic finish.

A Patent Leather Ankle boots with Black Dress

13. Knee-length Black Wrap Dress, Black Ankle Boots

A knee-length wrap dress can be a great choice for women over 50 looking for a classic and sophisticated look. Teamed with black ankle boots, this look can be perfect for a night out or an informal gathering. The wrap dress has a flattering silhouette, and the ankle boots add a bit of edge to the outfit.

For a more casual look, switch out the knee-length wrap dress for a long sleeve t-shirt or blouse tucked into a pair of high-waisted jeans. The ankle boots add a stylish element to the outfit and keep the look modern.

Knee-length Black Wrap Dress, Black Ankle Boots

Styling Tips for Ankle Boots Over 50

When styling ankle boots for women over 50, a few tips can help you achieve a fashionable and age-appropriate look. Here are some styling tips to consider:

  • Choose ankle boots with a moderate heel height for comfort and stability.
  • Opt for high-quality materials like leather or suede for a sophisticated look.
  • For versatility, stick to neutral colors such as black, brown, or navy.
  • Pair ankle boots with skinny jeans or trousers for a sleek and elongating effect.
  • Experiment with different boot heights to find the most flattering option for your legs.
  • Accessorize with confidence, adding complementary accessories to complete your look.

FAQ

Can I wear ankle boots with cropped pants?

Yes, ankle boots can be worn with cropped pants, creating a fashionable look. However, when pairing ankle boots with cropped pants, it’s important to consider the proportions and balance of the outfit. Opt for ankle boots with a sleek and streamlined design to avoid visually cutting off the leg line.

Are ankle boots suitable for women with wider calves?

Ankle boots can be suitable for women with wider calves, but finding the right style and fit is essential. Look for ankle boots with adjustable features like laces, buckles, or elastic panels, as they can provide a customized fit around the calf area. Choosing ankle boots with a wider opening or opting for booties with a slouchy or relaxed design can also accommodate wider calves.

How do I make my ankle boots more comfortable?

To make your ankle boots more comfortable, consider the following tips:
1. Choose the right size.
2. Break them in gradually.
3. Wear thicker socks for added padding.
4. Use moleskin or padding for areas irritating.
5. Insert insoles or cushions for extra support.
6. Adjust laces or buckles for a snug fit.

Are there any age-specific fashion rules to consider?

Fashion rules are becoming less rigid and more inclusive, with no strict age-specific guidelines. Personal style and individual preferences should dictate your fashion choices. However, certain considerations can enhance your overall look. For instance, prioritize comfort as you age and opt for footwear with better support. It’s also important to dress in a way that makes you feel confident and reflects your personality.

Is it fashionable to wear ankle boots with leggings?

Yes, wearing ankle boots with leggings can be a fashionable choice. It creates a sleek, streamlined look that is versatile and suitable for various occasions. However, when pairing ankle boots with leggings, consider the length. Ankle-length or slightly cropped leggings work best, allowing the ankle boots to be showcased.

Conclusion

Wearing ankle boots after 50 as a woman doesn’t have to be daunting. By choosing the right fit, style, and color pair of ankle boots and planning the rest of an outfit around them, wearing ankle boots as a part of any look can still be fashionable. With some effort and experimentation, you can always rock a trendy look with ankle boots.

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