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10 Most Comfortable Dressy Shoes for Women Over 50

By Sandra Roussy October 11, 2023 Makeup and Fashion

Are you looking for a new pair of dressy shoes? We should all have a pair of classic dressy shoes in our closet ready for when a special occasion or an invite to an event comes up.

The main problem with dressy shoes, if you aren’t used to wearing them, is comfort. We have all been there, crammed our toes into pointy shoes and heels too high for basic comfort and suffered blisters and achy arches.

Here are our favourite dressy shoes for older women:

  1. Hush Puppies Sofie Pump – Dressy pump with cushiony memory foam footbed.
  2. Naturalizer 27 EDIT REBECCA PUMP – Breathable lining and slip-resistant sole.
  3. Dr. Scholl’s Be Ready Wedge – Made from innovative recycled plastic bottle material.
  4. Stuart Weitzman PEARL FLAT – Luxurious shoes with pearl embellishments.
  5. NINE WEST Abay Smoking Flats – These flats, referred to as the new ballet flats and embraced by celebrities, boast a leg-lengthening pointy-toe design and a walkable low heel.
  6. Hush Puppies Angel II – Hush Puppies renowned comfort in a low block heel pump. Many colors to choose from.
  7. Naturalizer PADEN PUMP – These high heels offer versatile style and all-day comfort with a V-shaped topline, chunky block heel, synthetic upper, sustainable lining, pointed toe, Contour+ Comfort technology, and non-slip outsole.
  8. Dr. Scroll’s Be Adorned Wedge – Boost your style for any occasion with this ballet-inspired wedge pump featuring a chic metallic link accent.
  9. Nine West Brulia Dress Flats – boasting a trendy slingback design with a chic pointy toe and eye-catching chain detailing across the upper.
  10. CLARKS Ambyr Glow Asymmetrical Comfort Pumps – Most comfortable high-heel pump.

Many women stop wearing heels as they get older because of health issues like vertigo or arthritis, for example. But cute dress shoes by no means have to have 4-inch heels to be considered dressy. Some flats and loafers are created in luxurious materials and garnished with jewels or glitter, making them elegant and dressy. See below our super chic flat with pearl details on the heel.

What to Look for in Dressy Shoes

First, if you want comfort, look for shoes made with quality materials and insoles. Cheap shoes typically mean cheap quality which affects overall comfort.

Try wedge shoes or large stack heels if you can’t wear thin heels. Wedges and stack heels are trendy right now, so it’s a win-win for us.

Specialty brands like Naturalizer and Hush Puppies, for example, specialize in creating comfortable shoes. They innovate and design quality insoles and also offer various widths in certain models.

Most Comfortable Dressy Shoes for Mature Women

Here is our list of comfortable dressy shoes on the market today. Many are best-selling classics and are top-rated for style and comfort.

Hush Puppies Sofie Pump

Hush Puppies Sofie Pump

Crafted with comfort in mind, this pump is made with a soft flexible suede and has a cushiony memory foam footbed that provides instant, out-of-the-box comfort. This comfortable, slip-on silhouette is perfect with everything from dresses to jeans.

Naturalizer 27 EDIT REBECCA PUMP

Naturalizer 27 EDIT REBECCA PUMP

This block heel pump from Naturalizer has the classic Signature Contour+ fit system for true, all-day comfortable wear. The smooth lining and cushioned insole offer natural comfort and breathability. The rubber outsole design provides enhanced flexibility, shock absorption, and slip resistance.

Dr. Scholl’s Be Ready Wedge

Dr. Scholl’s Be Ready Wedge

Dr. Scholl’s lightweight flexible wedge is made from innovative recycled plastic bottle material. It has an antimicrobial, anti-odor Susterra® foam insole that is crafted from 11% bio-based materials with soft and lightweight cushioning, built-in arch support, and a molded heel cup.

Stuart Weitzman PEARL FLAT

Stuart Weitzman PEARL FLAT

These uniquely styled shoes from Stuart Weitzman are quite a splurge. The elegant flat offers a sophisticated spin on the timeless classic ballet flat with the addition of pearl embellishments on the small block heel.

Nine West Abay Smoking Flats 

Nine West Abay Smoking Flats 

Trending as the new ballet flats, smoking flats like the Abay feature a flattering pointy-toe design that elongates the legs and a comfortable low heel, making them a popular choice for women over 50.

Hush Puppies Angel II

Hush Puppies Angel II

This dressy shoe from Hush Puppies is simple and stylish and built with comfort in mind. It’s crafted with a sleek round toe and a cone-stacked heel. Easily dressed up or down. Reasonably priced, this comfortable pump is available in a variety of colors.

Naturalizer PADEN PUMP

Naturalizer PADEN PUMP

Indulge in the perfect high heels that offer versatile style and all-day comfort. Crafted with a V-shaped topline and chunky block heel, these elevated dress shoes feature a synthetic upper with a sustainable lining.

Dr. Scroll’s Be Adorned Wedge

Dr. Scroll’s Be Adorned Wedge

The design draws inspiration from the gracefulness of ballet shoes, while the stylish metallic link accent adds a touch of elegance. With its comfortable wedge heel, this pump offers a balance of height and comfort, making it an ideal choice for evening events. They can be paired with formal attire or easily dressed down for a more casual look.

Nine West Brulia Dress Flats

Nine West Brulia Dress Flats

Step up your style game with the Nine West Brulia dress flats, boasting a trendy slingback design with a chic pointy toe and eye-catching chain detailing across the upper. These flats are the perfect choice for effortlessly impressing on any occasion.

CLARKS Ambyr Glow Asymmetrical Comfort Pumps

CLARKS Ambyr Glow Asymmetrical Comfort Pumps

If you can still wear high heels then you will love these truly comfortable pumps from Clarks. The Ultimate Comfort foam footbeds bring all-day cushioning and the grippy sole will help with traction.

Read BEST WALKING SHOES FOR SENIOR WOMEN.

Also, 16 BEST SHOES FOR OLDER WOMEN.

Let’s Have a Conversation:

Where do you shop for your dressy shoes? Do you prefer pumps, wedges, or flats? Which dressy shoe on our list is your favorite? Tell us about it in the comments below.

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The Author

Sandra is the middle-aged woman you hear about who sheds everything she owns and sets out into the world to rediscover and redefine herself. After more than twenty years spent in the fashion industry designing collections for brands such as La Senza, Victoria’s Secret, and JACOB Lingerie, she shifted her path and pursued her longtime passion for writing, traveling, and photography. Sandra was published in the NY Times best selling book Eat Pray Love Made Me Do It. A deeply personal essay hand-picked by Elizabeth Gilbert about loss, facing fears, and going after dreams. Visit her website: www.sandraroussy.com

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