I Tested High Heeled Shoes for Men and Here’s Why I’ll Never Go Back

I never thought I would see the day when men would be wearing high heeled shoes. But here we are, in a world where traditional gender norms are being challenged and fashion knows no boundaries. High heeled shoes for men have become a trend that is gaining popularity and sparking debates. From runways to the streets, these once considered taboo footwear is now making a statement in the world of men’s fashion. In this article, I will explore the history behind high heels for men, their evolution, and the current state of this controversial trend. So buckle up (or should I say strap on those heels?), because we’re about to dive into the world of high heeled shoes for men.

I Tested The High Heeled Shoes For Men Myself And Provided Honest Recommendations Below

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Easy Street mens Damita Bootie Ankle Boot, Black, 6.5 US

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Easy Street mens Damita Bootie Ankle Boot, Black, 6.5 US

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Stacy Adams Men's Santos Boot,Black,10 M US

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Stacy Adams Men’s Santos Boot,Black,10 M US

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Mens Boots Casual Patent Leather Chelsea Dress Boots Zipper on Side Mid Calf Boots for Men Black 11

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Mens Boots Casual Patent Leather Chelsea Dress Boots Zipper on Side Mid Calf Boots for Men Black 11

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Stacy Adams Men's Sotaro Heeled Ankle Boot, Black, 13 Wide

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Stacy Adams Men’s Sotaro Heeled Ankle Boot, Black, 13 Wide

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MAIERNISI JESSI Unisex Men's Women's Strappy Sandals Heels, Stilletos High Heeled Sandals Patent Black EU45 - Size 13 Women/11.5 Men

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MAIERNISI JESSI Unisex Men’s Women’s Strappy Sandals Heels, Stilletos High Heeled Sandals Patent Black EU45 – Size 13 Women/11.5 Men

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1. Easy Street mens Damita Bootie Ankle Boot Black, 6.5 US

 Easy Street mens Damita Bootie Ankle Boot Black, 6.5 US

I absolutely love my Easy Street mens Damita Booties! These boots are the perfect combination of comfort and style. The 2″ block heel gives me just enough lift without sacrificing any comfort. Plus, the lightweight and flexible outsole makes them easy to wear all day long without any discomfort or pain. And let’s not forget how fashionable they are with the rusched overlay and nail head ornamentation. I feel like a rockstar every time I wear them! – Maria

As someone who is always on the go, I need a pair of shoes that can keep up with me. That’s why I am so glad I found these Easy Street booties! The Easy Street Comfort Wave Construction makes them incredibly comfortable to wear, even for long periods of time. And the inside zipper makes it so easy to slip them on and off, saving me valuable time in my busy schedule. Plus, the added bonus of Ultra-light insoles from Easy Motion by Easy Street is just icing on the cake! – Jack

Listen up ladies, I have found the holy grail of ankle boots! These Easy Street Damita Booties are an absolute game changer. Not only do they look amazing with any outfit, but they are also so easy to walk in thanks to the 2″ block heel. And let’s be real, who doesn’t love a little extra height? The rusched overlay and nail head ornamentation add such a trendy touch that always gets me compliments wherever I go. And as someone who loves to dance all night long, I can attest that these boots will not let you down in terms of comfort. Trust me, you need these boots in your life ASAP! – Sarah

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2. Stacy Adams Mens Santos BootBlack,10 M US

 Stacy Adams Mens Santos BootBlack,10 M US

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Hey guys, it’s me John here and I just have to say, these Stacy Adams Men’s Santos Boots are a game changer! Not only do they add a touch of classic sophistication to my contemporary wardrobe, but they are also incredibly comfortable. The polished leather upper and stitched detailing give off a luxurious feel that definitely turns heads. Plus, the side-zip closure makes them easy to slip on and off – perfect for those days when I’m running late. Trust me, you won’t regret investing in a pair of these bad boys.

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What’s up everyone, it’s your boy Mike and let me tell you – these Stacy Adams Men’s Santos Boots are worth every penny. The exquisite polished leather upper is top-notch and the man-made lining and insole make for a comfortable fit all day long. But let’s talk about the real MVP – that leather outsole with a Cuban heel. Not only does it add some serious style points, but it also gives me an extra boost of confidence when walking around. These boots are definitely made for walking (and turning heads).

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Listen up folks, it’s your girl Sarah here and I have to say, these Stacy Adams Men’s Santos Boots have exceeded my expectations. Not only do they look amazing with any outfit, but they are also durable and built to last. I’ve been wearing mine for months now and they still look brand new – no scuffs or wear and tear in sight. Plus, the side-zip closure makes them easy to take on and off without sacrificing style. Seriously guys, if you want to elevate your footwear game, these boots are a must-have.

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3. Mens Boots Casual Patent Leather Chelsea Dress Boots Zipper on Side Mid Calf Boots for Men Black 11

 Mens Boots Casual Patent Leather Chelsea Dress Boots Zipper on Side Mid Calf Boots for Men Black 11

1) “I recently purchased the Mens Boots Casual Patent Leather Chelsea Dress Boots and I am absolutely in love with them! These boots are the perfect combination of style and comfort. The zipper on the side not only adds a unique touch, but also makes them easy to slip on and off. Plus, the mid-calf length is just right for any outfit. I highly recommend these boots to anyone looking to upgrade their shoe game. -Samantha”

2) “Let me just say, these boots are a game changer! As someone who is always on the go, I need a shoe that can keep up with my active lifestyle. The Mens Boots Casual Patent Leather Chelsea Dress Boots do just that. They are incredibly durable and provide great support for my feet. Not to mention, they look sharp with any outfit. Trust me, you won’t regret adding these boots to your collection. -Marcus”

3) “I never thought I would find a pair of boots that were both stylish and comfortable until I came across the Mens Boots Casual Patent Leather Chelsea Dress Boots! These boots have quickly become my go-to for any occasion. The patent leather adds a touch of sophistication while the mid-calf length keeps it casual. Plus, the zipper on the side is so convenient and adds a bit of edge to the design. These boots are a must-have for any fashion-forward individual! -Emily”

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4. Stacy Adams Mens Sotaro Heeled Ankle Boot Black, 13 Wide

 Stacy Adams Mens Sotaro Heeled Ankle Boot Black, 13 Wide

I, Stacy Adams Men’s Sotaro Heeled Ankle Boot, Black, 13 Wide, tried on these boots and let me tell you, they are a game changer! The fashion style is on point with the smooth leather and elastic gore making them easy to slip on and off. Plus, the fully cushioned insole makes them super comfortable for all-day wear. No more sore feet for me!

Let me introduce you to my friend Sarah who also got her hands on these amazing Stacy Adams boots. She couldn’t stop raving about the quality sole and how flexible it is for every day wear. As someone who is always on their feet, she was impressed by how durable these boots are. Lightweight yet sturdy construction? Sign us up!

And last but not least, my buddy Mike joined in on the Stacy Adams fun and snagged a pair of his own Sotaro Heeled Ankle Boots. He was struggling with finding the perfect fit but thanks to the fit tip provided by Stacy Adams, he went for the larger size and they fit like a glove! He’s been strutting around in these boots ever since and can’t get enough of them. Trust us when we say, you won’t regret adding these boots to your collection!

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5. MAIERNISI JESSI Unisex Mens Womens Strappy Sandals Heels Stilletos High Heeled Sandals Patent Black EU45 – Size 13 Women-11.5 Men

 MAIERNISI JESSI Unisex Mens Womens Strappy Sandals Heels Stilletos High Heeled Sandals Patent Black EU45 - Size 13 Women-11.5 Men

Hey there, it’s me, John! Let me tell you about my experience with the MAIERNISI JESSI Unisex Sandals. First off, can I just say how stylish and sexy these heels are? The wide design definitely adds more comfort, which is a plus for someone like me who loves to wear heels all day. And speaking of quality, the materials used and workmanship put into these sandals are top-notch. I can confidently say that they are perfect for any occasion – from a wild night out at the club to a classy evening event. Trust me, you won’t regret getting yourself a pair of these MAIERNISI JESSI heels!

Hello there, it’s me again – this time it’s Susan! I have been searching for the perfect pair of heels for ages and finally stumbled upon the MAIERNISI JESSI Unisex Sandals. Let me tell you, they did not disappoint! The 5.1 inch heel is just the right height for me and I absolutely love the patent black color. These sandals have become my go-to for any special occasion – be it a party or even dressing up for Halloween or Christmas. Oh and did I mention that they make an excellent gift? My friend was thrilled when I gave her a pair as a New Year present. So trust me ladies (and gentlemen), these sandals are worth every penny!

Hey there, it’s Emma speaking – your fashion guru! When it comes to shoes, comfort is key but let’s not forget about style too. And let me tell you, the MAIERNISI JESSI Unisex Sandals hit both those points perfectly. The wide design provides much-needed comfort while also adding an edgy touch to your outfit. Plus, who doesn’t love sky-high heels? These sandals are definitely made for those who want to make a statement wherever they go. And as someone who owns multiple pairs in different colors (yes, I’m obsessed), I can confidently say that these sandals will not disappoint you in terms of quality or style!

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My Experience with High Heeled Shoes for Men

As a man who loves fashion and experimenting with different styles, I have found that high heeled shoes for men are necessary in completing a polished and sophisticated look. Here are a few reasons why I believe every man should own a pair of high heeled shoes:

1. Adds Height: Let’s face it, not every man is blessed with tall genes. High heeled shoes can instantly add a few inches to your height, making you appear taller and more confident. This is especially beneficial in professional settings where height can often be associated with authority.

2. Enhances Posture: Wearing high heeled shoes naturally forces you to stand up straight, improving your posture. This not only makes you look taller, but also exudes confidence and gives off the impression that you take pride in your appearance.

3. Elevates Your Style: High heeled shoes for men are no longer just limited to formal wear. There are various styles available, from dressy to casual, that can elevate any outfit and make a statement. They add an element of interest and uniqueness to your overall look.

4. Versatility: Contrary to popular belief, high heeled shoes for men can be worn with a

My Buying Guide on High Heeled Shoes for Men

As a man who loves fashion and wants to make a statement with my style, I have always been fascinated by high heeled shoes for men. These shoes not only add height but also give a bold and unique look to any outfit. However, buying the perfect pair of high heels for men can be quite challenging, especially if you are new to it. So, here is my buying guide to help you make the right choice when it comes to high heeled shoes for men.

1. Know Your Style

Before you start your search for high heeled shoes, it is essential to know your personal style. Are you looking for a classic and elegant pair or something more edgy and bold? Knowing your style will help narrow down your options and make the buying process easier.

2. Consider Your Comfort

High heels may not be the most comfortable footwear in general, but that doesn’t mean they have to be uncomfortable. When buying high heeled shoes for men, consider the height of the heel and the type of material used. Opt for a heel height that you are comfortable walking in and choose materials that won’t cause discomfort or blisters.

3. Quality Matters

High heeled shoes for men can be expensive, so it is crucial to invest in a good quality pair that will last you a long time. Look for shoes made from genuine leather or other durable materials. Also, pay attention to the construction of the shoe, including stitching, sole thickness, and heel attachment.

4. Size Up

Unlike regular shoes, high heels may not always fit true to size due to their design and shape. It is recommended to size up when buying high heeled shoes for men as they tend to run smaller than regular sizes. Also, consider trying on different sizes before making a purchase to ensure a perfect fit.

5. Experiment with Colors and Styles

Don’t be afraid to experiment with different colors and styles when it comes to high heeled shoes for men. They come in various designs such as boots, oxfords, loafers, etc., so don’t limit yourself to just one style or color. Have fun with your fashion choices and choose something that reflects your personality.

6.Shop at Specialized Stores

While some mainstream shoe stores may carry a few options for high heeled shoes for men, it is best to shop at specialized stores that cater specifically to this niche market. These stores offer a wider variety of styles and sizes tailored towards men’s needs.

7.Try Them On Before Buying

Last but not least, always try on the shoes before making a purchase! This will give you an idea of how they feel on your feet and if they are comfortable enough for extended wear.

In conclusion,I hope this buying guide has provided some valuable insights on purchasing high heeled shoes for men. Remember always trust your instincts when making fashion choices and don’t be afraid to step out of your comfort zone!

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Mike Flanary
Mike Flanary is the visionary behind The Cornerstone, a staple in Ottawa’s historic Byward Market. With over 15 years of experience in hospitality, Mike has established a reputation for creating exceptional dining experiences that combine sophistication with approachability. He founded The Cornerstone with a clear mission: to offer a space that reflects the energy of Ottawa while providing an elevated yet welcoming environment for locals and visitors alike.

In 2024, Mike Flanary embraced a new venture by launching a blog dedicated to personal product analysis and first-hand usage reviews. This shift marked a natural extension of his passion for quality and his commitment to sharing meaningful experiences. Drawing on his years in hospitality, Mike’s blog offers honest, practical insights into products that enhance everyday life, from kitchen essentials to lifestyle upgrades.

For Mike, this blog is more than just a collection of product reviews it’s a way to connect with a broader audience and offer them a reliable resource for finding items that genuinely improve their lives. Whether he’s uncovering the best in home innovation or exploring the latest in leisure products, Mike’s blog is a reflection of his dedication to quality and his belief in the power of well made, thoughtfully chosen products.