How to wear high heels after the age of 50 and feel fabulous…

If I invited you into my closet to view my collection of fabulous and fashionable shoes you would never think my shoe collection belonged to a grandmother with foot problems.

You see, dear reader, I have figured out a way to still “strut my stuff” in glamorous high heels after 50.

I had perfect feet and toes until I broke my ankle when I fell off a ladder wearing fashionable high heels many years ago. After that, I had surgery and wore a pink cast for six months with a smiley face painted on my big polished pink toe. I never stopped thinking about femininity and fashion–even with a cast! As well, I kept my spirits high because of my girlfriend’s support and my husband…whose kindness surpassed Florence Nightingale’s.

I assumed, incorrectly, that I would ‘walk’ right out of my surgeon’s office the day my cast came off; rush home and slip into a pair of my divine shoes.

I was in for a shock!

Darling, I could not walk! I could not bend my toes! I could not flex my left foot. And, I was in excruciating pain. I was beside myself and I was in tears. The swelling and pain were a clear sign that my body needed attention and healing. My foot and leg muscles felt so stiff after the cast was removed, and ive never realized how much stretching and therapy would be needed just to get moving again.

I looked at my doctor, and, I remember my exact words as I tried, unsuccessfully, to take my first steps. “Will I ever be able to walk again?” I asked.

My doctor responded, “I hope so.”

My heart sank.

That evening, I dressed for my ‘supposed’ celebration dinner in pants that were too long, (I never shortened them because I had faith!), a flat on my normal foot and a pink-striped sock given to me by my girlfriend, Linda, my sock supplier, during my six-month ordeal. I hobbled into the restaurant on the trusty walker that I thought I was going to give away. Not being able to wear my beloved heels was emotionally tough—ive felt the disappointment firsthand, and I know I’m not alone. In fact, a nationwide study found that 89% of women said uncomfortable shoes ruined an evening.

Did I allow my injured foot to prevent me from wearing my platforms in the future? (I love platforms!) Did I give away my high-heeled boots or gorgeous pumps? Of course not, darling!

I plunged into physical therapy from May through the following November with a vengeance. I graduated from a walker to a cane. After months of hard work, I was able to slowly flex my foot and toes so I could walk up and down steps carefully and with great caution. Sadly I had to regain my balance and my gait…but I did! However, it took all of my persistence and patience.

Wearing High Heels After 50: How My Feet Stayed Glamorous

Well my darling, especially any of you with problem feet, I began the long road back to normalcy by figuring out temporary solutions! I went out and bought fabulous flat shoes, from fun sneakers to fancy ballet flats. Comfortable alternatives to high heels can help alleviate foot pain after a long night out.

Let me share a few tips that worked for me…

• I bought yellow leather ‘high top’ sneakers that I ‘dared myself to wear with a beautiful dressy Pucci dress!
• For formal weddings and dressy occasions, I bought patent leather Chanel flats with pearls!
• For everyday wear, I bought flowered sneakers and two pairs of Lanvin flats in silver and deep blue because the colors would go with everything and they were not seasonal; the style of the shoe stretches, and the leather is very soft. The colour of these Lanvin flats is vibrant and long-lasting, which really enhances their appeal.

When buying new shoes, I paid close attention to positive reviews from other customers, which helped me choose styles that were both comfortable and stylish.

For my emotional well-being, I avoided shortening my slacks. I wanted to keep a positive attitude, dreaming of the day that I would be myself once again, strutting my stuff with confidence, feeling glamorous and amorous (for my husband!) in my high heel shoes. Through it all, I held onto hope that I would recover and wear my favorite heels again.

It has been years of adjustments. My once-perfect foot will never be the same. I often think back to the many special occasions when I wore my favorite heels, feeling elegant and stylish. I have nerve damage in four of my toes. My left foot is still slightly swollen from living in a cast for six months. The course of my recovery was long and challenging, but regaining the ability to walk in heels brought me a deep sense of joy and accomplishment. I developed a bunion, but I am happy to say, my broken bone healed perfectly. Now, I make sure to take a break when wearing heels for extended periods to keep my feet comfortable. I am strutting my stuff once again in shoes with heels, rocking them with style and assurance.

Wearing High Heels

There’s something undeniably magical about slipping into a pair of high heels. For many women, wearing high heels is more than just a fashion statement—it’s a way to feel glamorous, confident, sexy, and utterly fabulous. High heels can make women feel empowered and exude a sense of allure that boosts self-esteem. As we age, however, the pressure and strain that high heels can put on our feet and legs may make us think twice before reaching for that chic pair in our closet. But don’t worry, darling! Age is just a number, and with a few tips and a little know-how, older women can absolutely continue to wear high heels and feel as fashionable as ever. Whether you’re dressing up for a special night out or simply want to add a touch of sophistication to your everyday style, wearing high heels can still be a joyful part of your life. If you’re looking for the perfect balance between style and comfort, convertible heels are a great option—they appeal to those who want style without sacrificing comfort. In this article, I’ll share my favorite ways to wear high heels comfortably and confidently, so you can keep strutting your stuff and feeling fabulous at any age.

For more practical tips on foot care and relieving foot pain after wearing heels, read on.

Preparing Your Feet for High Heels After 50

As we grow wiser and more stylish with each passing year, our feet deserve a little extra love—especially if we want to keep wearing high heels and feeling amazing. After 50, it’s important to understand that our feet may become more sensitive, and a little preparation can make all the difference in comfort and confidence.

Start by giving your feet the attention they deserve. Before you slip into your favorite pair of heels, take a few minutes to stretch and strengthen your feet and legs. Simple exercises like toe curls and heel raises can help support your arch and improve your balance, making it easier to walk gracefully in high heels. A tennis ball is a wonderful tool for self-care—just roll it under your feet to massage away stiffness and tension, helping your body feel relaxed and ready for a stylish day or night out.

When choosing shoes, always look for good quality materials and a sturdy design that offers support where you need it most. A comfortable toe box and proper arch support are essential for reducing discomfort and protecting your feet from pain. Convertible heels are a fantastic option for women who want flexibility—these clever shoes can transform from heels to flats in seconds, making it easy to adapt to any situation, whether you’re at the office, running errands, or heading out for a night on the town.

Don’t forget to give your feet a break! If you’re wearing high heels for a long time, take regular moments to slip off your shoes, stretch your toes, and let your feet relax. When you’re at home or between events, opt for comfortable flats or slippers to help your feet recover and stay happy.

Listening to your body is key. If you notice any discomfort or pain, don’t force yourself to keep going—take a break, and if needed, consult a foot specialist who can help you create a personalized plan for comfort and support. With the right preparation and a little self-care, you’ll find it’s entirely possible to wear heels and look beautiful, no matter your age.

Remember, darling, the secret to wearing high heels after 50 is all about balance—between style and comfort, glamour and practicality. With a bit of planning and the right pair of shoes, you can continue to walk tall, feel confident, and show off your amazing style for years to come.

Choosing the Right Shoes

When it comes to wearing high heels, choosing the right shoes is truly the secret to looking and feeling your best. The perfect pair can make all the difference in terms of comfort, balance, and style—especially for older women who want to maintain their sense of sophistication without sacrificing support. Many shoes are thoughtfully designed specifically for comfort and support, ensuring you get both style and functionality. Consider the heel height and shape: thicker heels, like block heels, offer more stability and are easier on your feet than slender stilettos, while kitten heels provide a chic, feminine lift without the extra pressure. If you’re craving a bit of luxury, brands like Christian Louboutin offer stunning options that combine style with thoughtful design. Don’t forget to pay attention to the fit—shoes that are too tight or too loose can lead to discomfort or even injury. Features like gel inserts or cushioned insoles can add an extra layer of support, helping you wear high heels for longer periods without pain. Durable construction and built-in protection against hazards, such as nail penetration or external impacts, are also important for foot safety. Recovery shoes should offer arch support and cushioned soles for comfort. Convertible high heels can change into flats, providing versatility for the wearer, and their design allows for easy transformation from high heels to flats. By selecting shoes that suit your needs and your outfit, you’ll feel fabulous and confident, whether you’re heading out for a glamorous night or simply want to elevate your everyday look.

Solutions to Wear High Heels After 50 With Bad Feet

I buy shoes that are one or one and one-half sizes larger than my normal shoe size. My bunion no longer pains me! The shoes fit perfectly.

I took my high heel shoes to the shoemaker and had the heels cut down as far as possible. You have to be mindful to tell your shoemaker he must maintain the correct pitch. You will lose a quarter to at most a half-inch, but it makes a wonderful difference. You can also gently bend or soften the shoe material to improve comfort and ease wearability.

I was determined to try and save my shoes so I had all of my left shoes stretched at the shoemaker because that foot is a tiny bit swollen from my injury and I now have to deal with a bunion. Make sure to tell him to leave each shoe on the stretcher a day. It took me an entire summer and into the fall to complete the task.

I buy designer shoes that have a wide toebox front to house my damaged toes and bunion. Prada is the best in style and width for my foot. When choosing shoes, consider those with a strap for added support and stability, especially if you are wearing higher heels or platforms. Many women prefer convertible heels for their practicality during long events, as they can be adjusted or changed for comfort. Foldable shoes or accessories that fold are also a great option for easy storage in your bag and travel convenience.

Platform heels are a great option for stability and comfort, as the platform helps reduce pressure on the ball of your foot. There are many types of platforms available, from platform pumps to wedges and sandals, offering both style and comfort. Exploring different styles of heels and flats can help you find the best fit for your needs and preferences. Pay attention to the point of the shoe, as pointy-toed shoes can impact comfort, especially if you have foot issues. Certain shoe designs, like block heels and platforms, help distribute weight more evenly across your foot, making them more comfortable for long wear. Cushioning under the ball of the foot is important to prevent pain and discomfort, and supporting the balls of your feet with insoles or gel inserts can make a significant difference. The position of the heel is also key—having the heel slightly forward can improve balance and support. Be aware of the risk of wearing high heels, such as instability or foot strain, and choose designs that help mitigate these risks. Slip in and out of your shoes for relief during long events, and look for shoes with non-slip soles to prevent slipping. Insoles and inserts for added comfort can be found at most pharmacies, making it easy to enhance your shoe comfort. Some retailers offer easy returns and exchanges on orders, so you can try different shoe options with confidence.

For quick relief after wearing heels, keep a small massage ball or tennis ball in your bag to roll under your heel and release tension or reduce inflammation. Stretch your ankles and arches to alleviate discomfort, and try a seated toe stretch to restore mobility and reduce pain in the ball of your foot. Rolling a frozen water bottle under your foot can numb pain and further reduce inflammation. Incorporating natural anti-inflammatory foods into your diet can help with recovery from foot pain. Targeted exercises can also build the muscular support needed to handle high-heel stress.

I have learned how to manage my foot problem and I am happy to say, I no longer wear flats! As well, I think a styled shoe shows the personality of a woman…her flair; her style; her joie de vivre. So, my darling, my philosophy is:

• Do try and continue to buy glamorous and stylish shoes! It will give you a ‘lift’ in more ways than one.
• Be determined to solve your foot problems. Use your will and you can find solutions.
• Do not be shy in asking experts for help.
• As well, be a good listener, and then, follow advice.

Motivate yourself into action and wear high heels after the age of 50! A woman’s shoes are an important part of her style.

Are you still strutting your stuff? Or have you had to overcome foot problems so that you can feel glamorous? I’d love to hear your stories! LET’S TALK in the comments at the bottom of this page or on Facebook! 

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