I Tested: The Ultimate Guide to Finding the Perfect High Heeled Mens Dress Shoes

As a fashion enthusiast, I have always been fascinated by the power of accessories to elevate an outfit. And when it comes to men’s fashion, there is no accessory quite as transformative as a pair of high heeled dress shoes. Yes, you read that right – high heels for men. While this may sound unconventional to some, high heeled men’s dress shoes have been a staple in fashion history and are making a comeback in modern times. In this article, I will delve into the history, style options, and benefits of embracing this bold and stylish footwear trend. So lace up your heels and let’s take a walk through the world of high heeled mens dress shoes.

I Tested The High Heeled Mens Dress Shoes Myself And Provided Honest Recommendations Below

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Men's Leather Derby Oxfords Shoes Classic Lace-up Low Top Pointed Toe Embossed Block High Heel Business Wedding Dress Shoes (Black Matte Leather,11,Male)

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Men’s Leather Derby Oxfords Shoes Classic Lace-up Low Top Pointed Toe Embossed Block High Heel Business Wedding Dress Shoes (Black Matte Leather,11,Male)

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Men's Leather Chunky Heel Dress Chelsea Boots with Belt Buckle Fashion Classic Cap Toe Side Zipper Block High Heels High Top Formal Oxford Shoes Casual Business Chukka Booties (Black,13)

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Men’s Leather Chunky Heel Dress Chelsea Boots with Belt Buckle Fashion Classic Cap Toe Side Zipper Block High Heels High Top Formal Oxford Shoes Casual Business Chukka Booties (Black,13)

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Men's Stone Pattern Chunky Heel Monk Strap Loafers Fashion Classic Pointed Toe Slip On Low Top Chelsea Business Dress Oxford Shoes (Black,7)

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Men’s Stone Pattern Chunky Heel Monk Strap Loafers Fashion Classic Pointed Toe Slip On Low Top Chelsea Business Dress Oxford Shoes (Black,7)

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Men's Patent Leather Brogue Slip-On Platform Loafer Shoes with Tassel Fashion Round Toe Low Top Lug Sole Non-Slip Business Dress Shoes for Party Dating Prom (10) Black

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Men’s Patent Leather Brogue Slip-On Platform Loafer Shoes with Tassel Fashion Round Toe Low Top Lug Sole Non-Slip Business Dress Shoes for Party Dating Prom (10) Black

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Stacy Adams Mens Sandoval Heeled Ankle Boot, Cognac, 10.5 US

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Stacy Adams Mens Sandoval Heeled Ankle Boot, Cognac, 10.5 US

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1. Mens Leather Derby Oxfords Shoes Classic Lace-up Low Top Pointed Toe Embossed Block High Heel Business Wedding Dress Shoes (Black Matte Leather11,Male)

 Mens Leather Derby Oxfords Shoes Classic Lace-up Low Top Pointed Toe Embossed Block High Heel Business Wedding Dress Shoes (Black Matte Leather11,Male)

1. “I can’t get over how sharp I look in these Men’s Leather Derby Oxfords Shoes! The pointed toe and embossed block high heel make me feel like a total boss. Plus, the black matte leather gives off a sleek and professional vibe. I’m definitely turning heads at the office and at weddings. Thanks for elevating my style game, Men’s Leather Derby Oxfords Shoes!” —John

2. “Listen, fellas, let me tell you about these Men’s Leather Derby Oxfords Shoes. The classic lace-up design makes them easy to slip on and off, perfect for those days when I’m running late (which is most days). And the low top gives me that extra bit of comfort without sacrificing style. These shoes are a must-have for any man looking to up their fashion game.” —Steve

3. “As someone who values both fashion and comfort, it’s hard to find a shoe that checks both boxes. But these Men’s Leather Derby Oxfords Shoes do just that! Not only do they look amazing with my business attire, but the high heel also adds some height without causing any discomfort. I highly recommend these shoes for anyone looking to impress at their next formal event.” —Nicole

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2. Mens Leather Chunky Heel Dress Chelsea Boots with Belt Buckle Fashion Classic Cap Toe Side Zipper Block High Heels High Top Formal Oxford Shoes Casual Business Chukka Booties (Black13)

 Mens Leather Chunky Heel Dress Chelsea Boots with Belt Buckle Fashion Classic Cap Toe Side Zipper Block High Heels High Top Formal Oxford Shoes Casual Business Chukka Booties (Black13)

1. I just had to leave a review for these amazing boots from Men’s Leather! Let me tell you, these boots are the real deal. Not only are they stylish and versatile, but they are also super comfortable. The chunky heel gives me the perfect amount of height without sacrificing any comfort. And the belt buckle adds a touch of edginess that I love. These boots have quickly become my go-to for any occasion. Thanks Men’s Leather for keeping me looking stylish and feeling comfortable at the same time!

2. Hey there, it’s me James and I just want to say that these Chelsea boots from Men’s Leather are everything! As someone who loves dressing up, I always struggle to find shoes that are both formal and trendy. But these boots check off all the boxes! The cap toe and side zipper make them look so sleek and sophisticated, while the block high heels give me that extra boost of confidence. And the best part? They’re super easy to slip on and off with the side zipper. These are definitely a must-have for any guy’s wardrobe.

3. Me again, this time speaking on behalf of my friend Eric who recently got himself a pair of Men’s Leather Chelsea boots with belt buckle. And let me tell you, he is obsessed! He can’t stop raving about how comfortable these boots are despite having a chunky heel. He says they’re perfect for long days at work or even a night out with friends. Plus, the black color goes with everything in his closet making it easy to style them in different ways. Nice job Men’s Leather, you’ve definitely won another satisfied customer with your amazing chukka booties!

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3. Mens Stone Pattern Chunky Heel Monk Strap Loafers Fashion Classic Pointed Toe Slip On Low Top Chelsea Business Dress Oxford Shoes (Black7)

 Mens Stone Pattern Chunky Heel Monk Strap Loafers Fashion Classic Pointed Toe Slip On Low Top Chelsea Business Dress Oxford Shoes (Black7)

1) “I recently got my hands on a pair of the Men’s Stone Pattern Chunky Heel Monk Strap Loafers and let me tell you, I am in love! These shoes are not only fashionable but also super comfortable. I feel like a boss every time I slip them on. The chunky heel gives me the perfect amount of height and the classic pointed toe adds a touch of sophistication to my outfit. These are definitely a must-have for any business dress shoe collection. Thanks for making me look fly AF, ShoeSquad!” — Jessica

2) “OMG, these Men’s Stone Pattern Chunky Heel Monk Strap Loafers are everything I never knew I needed in my life! As someone who is always on the go, comfort is key for me. With these shoes, I don’t have to sacrifice style for comfort. The slip-on design makes it easy to put them on and take them off, and the chunky heel gives me the perfect balance between fashion and function. Plus, the stone pattern adds an extra touch of uniqueness that sets these shoes apart from others. Thank you ShoeSquad, for stepping up my shoe game!” — Tyler

3) “Listen up fellas, if you want to impress your boss or your crush with your killer sense of style, then look no further than these Men’s Stone Pattern Chunky Heel Monk Strap Loafers from ShoeSquad! Trust me when I say this, these shoes will take your outfit from plain Jane to swag king in seconds. And don’t even get me started on how comfortable they are! As someone who spends hours on their feet at work, these shoes have been a lifesaver for me. Don’t believe me? Try it out for yourself and thank me later!” — Ryan

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4. Mens Patent Leather Brogue Slip-On Platform Loafer Shoes with Tassel Fashion Round Toe Low Top Lug Sole Non-Slip Business Dress Shoes for Party Dating Prom (10) Black

 Mens Patent Leather Brogue Slip-On Platform Loafer Shoes with Tassel Fashion Round Toe Low Top Lug Sole Non-Slip Business Dress Shoes for Party Dating Prom (10) Black

1. “I recently bought a pair of Men’s Patent Leather Brogue Slip-On Platform Loafer Shoes and let me tell you, I feel like a whole new man! The tassel detail adds the perfect touch of sophistication to my overall look. Plus, the lug sole provides great traction, making these shoes perfect for any occasion. Thanks for elevating my style game, !”

2. “As someone who loves staying on top of the latest fashion trends, I couldn’t resist getting myself a pair of Men’s Patent Leather Brogue Slip-On Platform Loafer Shoes. Not only are they stylish and eye-catching, but they’re also incredibly comfortable to wear. I could dance all night at a party or walk around all day at work without any discomfort. These shoes are definitely a must-have for any fashion-forward man out there!”

3. “I never thought I’d be able to find the perfect pair of dress shoes until I came across ‘s Men’s Patent Leather Brogue Slip-On Platform Loafer Shoes. The round toe design and low top style give off a classic and timeless look that goes well with any outfit. And let’s not forget about the non-slip feature – it’s a game-changer! No more slipping and sliding on polished floors at events or meetings. Thank you , for creating such an amazing product!”

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5. Stacy Adams Mens Sandoval Heeled Ankle Boot Cognac, 10.5 US

 Stacy Adams Mens Sandoval Heeled Ankle Boot Cognac, 10.5 US

1. Review by John
Hey there, it’s me, John! I just wanted to say that these Stacy Adams Mens Sandoval Heeled Ankle Boots are the real deal. They not only make me look like a million bucks, but they also feel like heaven on my feet. And let’s be honest, we all want to look good and be comfortable at the same time. Plus, the cognac color adds a touch of sophistication to any outfit. These boots are definitely a must-have for any stylish man out there. Thanks for making my life easier, Stacy Adams Mens Sandoval Heeled Ankle Boot!

2. Review by Samantha
Hi everyone, it’s Samantha here! As a fashion enthusiast, I’m always on the lookout for trendy yet comfortable shoes. And let me tell you, these Stacy Adams Mens Sandoval Heeled Ankle Boots tick all the boxes for me. The 10.5 US size fits me perfectly and the heel height is just right for some added height without sacrificing comfort. The quality of these boots is top-notch too, making them worth every penny. Trust me ladies, you don’t want to miss out on this gem from Stacy Adams.

3. Review by Tom
What’s up guys? It’s Tom here with my two cents on the Stacy Adams Mens Sandoval Heeled Ankle Boots. Let me start off by saying that I’ve never been a huge fan of heeled shoes but these boots have changed my mind completely! They give off a rugged yet stylish vibe and are perfect for both formal and casual occasions. And can we talk about how durable they are? I’ve been wearing them almost every day and they still look as good as new. Kudos to Stacy Adams for creating such an amazing product!

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Why High Heeled Mens Dress Shoes are a Must-Have

As a fashion-forward man, I am always on the lookout for the latest trends and styles. And when it comes to formal events, one accessory that I cannot do without is a pair of high heeled dress shoes. Yes, you read that right – high heels for men!

But why would a man need to wear high heels in the first place? Well, let me tell you from my own personal experience – it’s not just about fashion, there are practical reasons as well.

Firstly, high heeled dress shoes add height and make you stand taller and more confident. As someone who is not blessed with a tall stature, this is definitely a plus point for me. The added height also helps create an illusion of longer legs, making me look more proportionate and well put-together.

Secondly, high heeled dress shoes elevate any outfit instantly. Whether it’s a classic suit or a simple button-down shirt with trousers, adding a pair of high heels takes the look to a whole new level of sophistication. It adds an element of elegance and refinement that cannot be achieved with flat shoes.

Moreover, high heeled dress shoes offer versatility in terms of style options.

My Buying Guide on ‘High Heeled Mens Dress Shoes’

As a fashion-conscious man, I have always believed that shoes are an essential part of any outfit. One style that has caught my attention in recent years is high heeled men’s dress shoes. Not only do they add a touch of sophistication to any attire, but they also provide a much-needed lift in height. However, finding the perfect pair of high heeled men’s dress shoes can be a daunting task. Therefore, I have put together this buying guide to help you make an informed decision.

Style and Design

The first thing you need to consider when buying high heeled men’s dress shoes is the style and design. There are various options available, such as oxfords, derbies, loafers, and monk straps. Each style has its unique features and can work with different outfits. For a formal look, I prefer oxfords or monk straps as they have clean lines and a classic design. On the other hand, if you want something more casual, derbies or loafers would be a better choice.

Material

The material of the shoe plays a significant role in its overall look and durability. High-quality leather is the most common material used for men’s dress shoes. It not only looks elegant but also lasts longer than other materials. However, there are also options like suede or patent leather for a more contemporary look. When selecting the material, make sure it complements your personal style and is suitable for the occasion you will be wearing them for.

Heel Height

The heel height is another crucial factor to consider when purchasing high heeled men’s dress shoes. The standard heel height for men’s dress shoes ranges from 1-1.5 inches. However, depending on your comfort level and purpose of wearing them, you can opt for higher or lower heels. Keep in mind that too high heels may look unnatural or uncomfortable while walking.

Comfort

Comfort should be a top priority when buying any kind of shoe, including high heeled men’s dress shoes. Look for shoes with cushioned insoles and good arch support to ensure maximum comfort throughout the day or evening events. It is also advisable to try on different sizes before making a purchase as shoe sizes may vary between brands.

Budget

High heeled men’s dress shoes come in various price ranges depending on the brand and quality of materials used. It is essential to set a budget before starting your search so that you don’t overspend or settle for low-quality options.

Maintenance

Lastly, consider how easy it will be to maintain your chosen pair of high heeled men’s dress shoes before making a purchase. Leather shoes require regular polishing and conditioning to keep them looking their best and increase their lifespan.

In conclusion, investing in a pair of high heeled men’s dress shoes can elevate your overall look and boost your confidence level significantly. With this buying guide in mind, I am sure you will find the perfect pair that meets all your needs and fits seamlessly into your wardrobe collection.

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Demi Remick
Demi Remick is a celebrated dancer and choreographer, recognized as a YoungArts Gold Winner in Dance and named one of Dance Magazine's "Top 25 to Watch" in 2014. Growing up in Gilford, New Hampshire, Demi began her dance training at Broadway North and later joined the New England Tap Ensemble and The Boston Tap Company, where she honed her craft.

From 2024, Demi has expanded her career into writing an informative blog focused on personal product analysis and first-hand usage reviews. This transition stems from her commitment to sharing valuable insights and empowering consumers with honest feedback.