How to Wear Ankle Boots Over 50

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How to Wear Ankle Boots Over 50

Ankle boots are a versatile shoe style perfect for women over 50 looking to add polish and flair to any outfit.

With so many options, from heel heights to colors, ankle boots allow you to accentuate your style.

This comprehensive guide will provide tips on how to thoughtfully choose flattering ankle boot silhouettes, pair them with pants, skirts, and dresses, and incorporate them into both everyday and glammed-up looks.

With advice on styling ankle boots tailored specifically for the over-50s, you can exude confidence and chicness through your footwear.

Factors to Consider When Selecting Ankle Boots Over 50

The key to successfully styling ankle boots over 50 starts with choosing options that complement your body type and style preferences.

Consider these factors when shopping:

Heel Height

Limit heel height to 3 inches or below for optimal comfort and balance. Block heels are a great choice over stilettos. Also, look for options with padded footbeds.

Toe Shape

Tapered almond or pointy-toe ankle boots visually elongate the leg compared to round-toe styles. Pointy options also add polish.

Hardware and details

Look for functional hardware like side zippers or elastic panels that make getting boots on and off easy. Avoid over-embossed styles.


Soft, pliable leather or suede ankle boots prevent digging or discomfort. Also, look for moisture-wicking linings. Say no to cheap vinyl boots.


Versatile neutral colors like black, brown, grey, tan, navy, and red provide flexibility across outfits. Metallics add glamour to events.

The right heel, toe shape, height, materials, and color help keep ankle boots elegant and proportional to the leg.

How to Style Ankle Boots Over 50 with Pants

Ankle boots pair effortlessly with pants for everyday errands, casual office looks, and relaxed weekend activities. Consider these pairings:

Skinny Jeans

A slim fit through the ankles maintains clean lines from the waist to the ankle boots. Try a motorcycle-inspired look with a slouchy sweater.

With Trousers

Wide-leg, flowy trousers layered over ankle boots anchor the volume while showing the shape. Add an untucked button-up shirt.

With boyfriend jeans

Cuffed boyfriend jeans with ankle boots create visual contrast. Choose boots with edgy hardware details to complement the relaxed vibe.

With Cigarette Pants

The slim cut of cigarette pants prevents a choppy transition to ankle boots. Finish with a blazer and satchel bag for polished perfection.

Aim to have pants hemmed to hit at the ankle bone or slightly above, depending on your height and preferred proportions.

How to Wear Ankle Boots Over 50 with Skirts and Dresses

Beyond pants, experiment with mixing ankle boots with skirts and dresses too. Here are some sharp pairings:

With pencil skirts

Midi or knee-length pencil skirts and heeled ankle booties exude professional refinement. Choose a neutral brown suede pair.

With Sweater Dresses

Feminine fitted sweater dresses take on evening flair when paired with heeled black leather booties and opaque tights.

With Leather Skater Skirts

For an unexpected casual pairing, style lace-up combat ankle boots with a leather skater skirt and cropped moto jacket.

With Maxi Skirts

Pointed-toe suede booties peeking out from a maxi skirt keep the look modern. Accessorize with layered necklaces.

Aim for a 2-4 inch skirt length above the ankle boot, depending on your height and style objectives. Play with boot and skirt colors.

Dressing Up Ankle Boots Over 50 For Occasions

When an event calls for added allure, style ankle boots accordingly.

With cocktail dresses

Metallic and glitter-infused ankle boots complement figure-hugging cocktail dresses seamlessly. Let the shoes shine.

With formal gowns

Subtle-heeled booties work well with floor-length formal gowns; just be sure to hem the dress to show them off.

With leather leggings

Sculptural block-heeled booties paired with leather leggings and an oversized drapey blouse project effortless coolness.

With wide-leg jumpsuits

Give wide-leg jumpsuits a modern twist by finishing with pointy-toed booties in a coordinating color.

Have fun mixing textures and playing with colors. Ankle boots keep outfits exciting for evenings out.

Expert Tricks for Ankle Boots Over 50

Use these pro tips and tricks to take your ankle boot styling up a notch:

  • Bring folding ballet flats in your bag to swap if your ankles or feet get tired of heels.
  • Use double-sided fashion tape to prevent boot shafts from sliding down the calves.
  • Shop for boot socks that don’t bunch around ankles if you dislike bare legs.
  • Have boots professionally stretched width-wise if tight around the ball of the foot.
  • Use moisturizing creams like Vaseline on heels and ankles to prevent dryness or rubbing.
  • Opt for side zippers or elastic gore panels that make getting boots on easier.
  • Spray waterproofing treatment on suede boots to avoid staining.

With the right tricks, ankle boots keep you looking and feeling amazing all day long.

FAQs about styling ankle boots over 50

Still have questions about wearing ankle boots stylishly over 50? Here are some common FAQs:

Can I wear ankle boots to the office over 50?

Yes, focus on heeled styles 2 inches or below in leather or suede. Pair with cigarette pants or pencil skirts and blazers.

Do ankle boots work over 50 for formal events?

Absolutely. Metallic and glittery ankle boots complement cocktail attire and dress elegantly. Just be sure to hem dresses to show off the booties.

What heel height is optimal for ankle boots over 50?

Limit heel height to around 2–3 inches for ideal comfort and walkability. Block, chunky heels are best over thin stilettos.

What if I have thicker calves?

Look for ankle boots with adjustable laces, zippers, or elastic gore panels to accommodate calves comfortably. Leather and suede also stretch over time.

Can I still wear ankle boots if I have balance issues?

Prioritize low-block heels and flat ankle boot styles. Also, look for slip-resistant rubber soles and shafts that provide ankle stability.


Ankle boots keep you looking stylish and feeling confident over 50 when you select the right heel heights, materials, and silhouettes to flatter your figure.

Pair them thoughtfully with pants, skirts, and dresses for daytime outings or special events.

With so many options, ankle boots can become your go-to versatile footwear well into your 50s and beyond.

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