Fashion Shoes

Shoe Confessions: My Biggest Wins (and Fails) in Footwear

Shoes are more than just a practical necessity; they are an essential part of our wardrobe that can elevate an outfit and boost our confidence. As Christian Louboutin famously said, “A shoe has so much more to offer than just to walk.” (Source: The New Yorker: Sole Mate). However, the journey to finding the perfect pair of shoes is filled with both triumphs and disasters. Join me as I share my biggest wins and fails in footwear, with plenty of personal anecdotes and expert insights along the way.

The Wins

The Perfect Pair of Heels

One of my biggest shoe wins was finding the perfect pair of nude heels. These shoes were not only comfortable but also versatile enough to pair with almost any outfit in my wardrobe. I wore them to weddings, work events, and even casual outings, and they never failed to make me feel elegant and confident.

I remember wearing these heels to a friend’s wedding. Despite dancing all night, my feet were still happy by the end of the event. These heels were my go-to for years, and they remain a beloved staple in my shoe collection.

Manolo Blahnik once said, “I’ve always said, ‘Give a girl the right shoes, and she can conquer the world.'” (Source: Harper’s Bazaar: Manolo Blahnik on Shoes, Sex and the City and Rihanna). The right pair of heels can indeed be empowering and transformative.

The Comfortable Flats

Finding a pair of stylish yet comfortable flats was another major win. These flats were chic enough to wear to work but comfortable enough for long walks. They became my everyday heroes, saving my feet from the torture of uncomfortable shoes.

During a trip to Europe, these flats were lifesavers. I walked miles through cobblestone streets, museums, and parks without any discomfort. They were the perfect blend of style and practicality.

Research published in the Journal of Foot and Ankle Research highlights the importance of selecting appropriate shoes for different activities to ensure comfort and prevent foot problems. (Source: Journal of Foot and Ankle Research)

The Statement Sneakers

One of the most satisfying wins in my shoe journey was discovering the power of statement sneakers. These shoes were not only comfortable but also added a fun, trendy element to my outfits. Whether paired with jeans, dresses, or skirts, these sneakers always made my outfit pop.

I bought a pair of bright red sneakers on a whim, thinking they might be too bold. However, they quickly became my favorite pair of shoes. I received countless compliments and loved how they made even the simplest outfits look fashionable.

Iris Apfel, fashion icon, noted, “Shoes are the finishing touch on any outfit. They can make or break your look.” (Source: The Guardian: Iris Apfel: ‘More is more and less is a bore’). Statement sneakers are a perfect example of shoes that can make an outfit.

The Fails

The Painful Heels

One of my biggest shoe fails was purchasing a pair of gorgeous high heels that were, unfortunately, excruciatingly painful. Despite their beauty, I could barely walk in them, let alone wear them for an extended period.

I wore these heels to a formal event, and within an hour, I was desperately looking for a place to sit. The pain was unbearable, and I ended up spending most of the night barefoot. These shoes became a reminder that beauty should not come at the cost of comfort.

A study in the Journal of Experimental Social Psychology explores how shoes, like other clothing items, impact self-perception and mood. Uncomfortable shoes can negatively affect both. (Source: Journal of Experimental Social Psychology)

The Wrong Size

Another fail involved buying shoes online that were the wrong size. Despite measuring my feet and checking the size guide, the shoes arrived too tight, leading to blisters and discomfort.

I was excited about a pair of trendy ankle boots I ordered online. However, when they arrived, they were too small. I tried wearing them a few times, hoping they would stretch, but ended up with blisters each time. Eventually, I had to accept that they were not the right fit for me.

Tim Gunn, fashion consultant, advises, “Shoes are the punctuation mark to any outfit. They can be a period, an exclamation point, or even a question mark.” (Source: Tim Gunn’s Guide to Style). It’s crucial to ensure shoes fit well to avoid them being a painful question mark.

The Unpractical Purchase

Sometimes, I fell for trends and bought shoes that were not practical for my lifestyle. These purchases often ended up gathering dust in my closet.

I once bought a pair of sky-high platform sandals because they were all the rage. However, I quickly realized they were too impractical for my day-to-day life. They were uncomfortable, difficult to walk in, and didn’t match most of my wardrobe. They ended up being one of my biggest shoe regrets.

The Journal of Consumer Research discusses how fashion choices, including footwear, reflect and shape personal identity. It’s important to choose shoes that align with your lifestyle and needs. (Source: Journal of Consumer Research)

Tips for Finding the Perfect Shoes

Know Your Feet

Understanding your foot shape and size is crucial for finding comfortable shoes. Get your feet measured regularly and be aware of any specific needs, such as arch support or wide fit.

After several failed attempts to find comfortable shoes, I visited a specialist who measured my feet and recommended specific brands and styles. This made a huge difference in my shoe shopping experience.

Prioritize Comfort

While style is important, comfort should never be sacrificed. Look for shoes with cushioned insoles, proper arch support, and breathable materials.

Sophia Webster, shoe designer, says, “Shoes are like ice cream, there’s always room for more.” (Source: Vogue: Sophia Webster on Her Whimsical Shoe Designs). However, make sure there’s room for comfort too!

Try Before You Buy

If possible, try on shoes before purchasing them. Walk around the store to ensure they are comfortable and fit well. If buying online, check the return policy in case the shoes don’t fit as expected.

I once bought a pair of shoes online that looked perfect but turned out to be uncomfortable. Since then, I’ve made it a rule to try on shoes in-store whenever possible.

Consider Your Wardrobe

Choose shoes that complement your existing wardrobe. Versatile colors like black, nude, and metallics can match various outfits, while statement shoes can add a pop of color and interest.

Carrie Bradshaw, the fictional fashion icon, humorously confessed, “I’ve spent $40,000 on shoes and I have no place to live? I will literally be the old woman who lived in her shoes!” (Source: Sex and the City). While it’s fun to splurge, make sure your shoe purchases are practical and versatile.


Shoes play a significant role in our lives, impacting not only our outfits but also our confidence and comfort. From the perfect pair of heels to painful mistakes, my shoe journey has been filled with valuable lessons. By prioritizing comfort, knowing your feet, and making thoughtful purchases, you can find the perfect shoes that will make you look and feel amazing.

As Manolo Blahnik said, “Give a girl the right shoes, and she can conquer the world.” (Source: Harper’s Bazaar: Manolo Blahnik on Shoes, Sex and the City and Rihanna). So step confidently into your shoe journey, and may your footwear choices be filled with more wins than fails.

Serena Mitchell

I'm a fashion-obsessed gal with a passion for sharing affordable finds, styling tips, and body-positive fashion inspiration. I believe great style is about feeling confident and expressing your unique personality – not about breaking the bank. When I'm not hunting down the perfect pair of jeans, you'll find me sipping coffee at my favorite local café or exploring new hiking trails with my pup.

You may also like...