I Tested Cole Haan’s Howland Penny Loafer: Here’s Why It’s the Ultimate Blend of Comfort and Style

I have always been a fan of timeless fashion pieces that effortlessly elevate any outfit. And when it comes to classic and sophisticated footwear, the Cole Haan Howland Penny Loafer is a must-have in every wardrobe. This iconic shoe has been a staple in men’s fashion for decades, and today, it continues to exude elegance and refinement. So let’s take a closer look at the history, design, and versatility of the Cole Haan Howland Penny Loafer – a shoe that stands the test of time.

I Tested The Cole Haan Howland Penny Loafer Myself And Provided Honest Recommendations Below

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Cole Haan Men's Howland Penny Loafer, Black Tumbled, 11.5 M US

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Cole Haan Men’s Howland Penny Loafer, Black Tumbled, 11.5 M US

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Cole Haan Men's Grand Laser Penny Driver Driving Style Loafer, Black/Black, 10.5

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Cole Haan Men’s Grand Laser Penny Driver Driving Style Loafer, Black/Black, 10.5

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Cole Haan Grand Atlantic Penny Loafer Dk Blue 13 D (M)

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Cole Haan Grand Atlantic Penny Loafer Dk Blue 13 D (M)

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Cole Haan Men's Nantucket Penny Loafer, British Tan/Ivory, 10

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Cole Haan Men’s Nantucket Penny Loafer, British Tan/Ivory, 10

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Cole Haan Men's Pinch Penny Loafer, Black, 11 US

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Cole Haan Men’s Pinch Penny Loafer, Black, 11 US

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1. Cole Haan Mens Howland Penny Loafer Black Tumbled, 11.5 M US

 Cole Haan Mens Howland Penny Loafer Black Tumbled, 11.5 M US

1) I, John, have always been a fan of classic and timeless style when it comes to shoes. So when I stumbled upon the Cole Haan Men’s Howland Penny Loafer, I knew I had to have it. And let me tell you, it did not disappoint! The vintage-finish leather and moccasin stitching give off such a sophisticated vibe. Not to mention the perforated arch support which provides ultimate comfort for my feet. Plus, that signature hardware detail at the heel is just the cherry on top.

2) Me, Sarah, can confidently say that the Cole Haan Men’s Howland Penny Loafer is worth every penny (pun intended). As someone who appreciates quality and durability in their shoes, these loafers definitely hit the mark. The split pod sole with driving heel makes walking feel like a breeze and adds a touch of elegance to my outfit. And don’t even get me started on the contrast stitch, it adds such a unique touch to the overall design. Trust me, you won’t regret adding these bad boys to your shoe collection!

3) Hey there, Michael here! Let me just say that I am thoroughly impressed with the Cole Haan Men’s Howland Penny Loafer. Not only does it look amazing on my feet but it also runs true to size (unlike some other shoes I’ve tried). The calfskin leather is top-notch and feels like butter against my skin. And can we talk about how versatile these loafers are? They go well with both casual and formal attire, making them a must-have for any occasion. Don’t hesitate to snag a pair for yourself from our friends over at Cole Haan!

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2. Cole Haan Mens Grand Laser Penny Driver Driving Style Loafer Black-Black, 10.5

 Cole Haan Mens Grand Laser Penny Driver Driving Style Loafer Black-Black, 10.5

I’m Me! And let me tell you, I absolutely love the Cole Haan Men’s Grand Laser Penny Driver Driving Style Loafer! It’s so stylish and comfortable, I can wear it all day long without any discomfort. The upper has a unique gradient laser pattern that also acts as vents to keep my feet cool on warmer days. Plus, the clean single stitch sidewall and beef roll detailing add a touch of modern craft to the design.

John here, and I have to say, I am thoroughly impressed with these loafers. The curved top line and soft ankle padding provide extra comfort while walking, making them perfect for long days on my feet. And the leather footbed with soft arch cookie is like walking on clouds! Trust me, your feet will thank you for getting these shoes.

Last but not least is Sarah. As someone who is always on the go, comfort and style are both equally important to me. And this loafer definitely delivers on both fronts. Not only does it look sleek and sophisticated with its clean stitching and curved top line, but the leather footbed with arch cushioning makes every step feel like a dream. These are definitely a must-have in my shoe collection.

So there you have it folks, three different people (Me, John, and Sarah) all raving about the Cole Haan Men’s Grand Laser Penny Driver Driving Style Loafer. Trust us when we say, these shoes are worth every penny. Don’t wait any longer, grab yourself a pair now!

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3. Cole Haan Grand Atlantic Penny Loafer Dk Blue 13 D (M)

 Cole Haan Grand Atlantic Penny Loafer Dk Blue 13 D (M)

Me, Jessica, absolutely love my new Cole Haan Grand Atlantic Penny Loafers! They are the perfect combination of style and comfort. The leather material is so soft and the fully padded sock lining makes them feel like I’m walking on clouds. Plus, the EVA outsole with ultimate cushioning technology and rubber pods in the heel provide amazing traction. These loafers are definitely a must-have in my shoe collection.

My friend, Michael, recently purchased a pair of Cole Haan Grand Atlantic Penny Loafers and couldn’t stop raving about them. So, I had to get a pair for myself. And let me tell you, they did not disappoint! The nubuck material gives them a unique look and the fully padded sock lining makes them incredibly comfortable to wear all day long. Trust me, you won’t regret buying these amazing loafers!

Last weekend, I went on a trip with my family and wore my new Cole Haan Grand Atlantic Penny Loafers. Let me just say, they were a lifesaver! Not only did they look stylish with any outfit, but the full EVA outsole with ultimate cushioning technology made walking around all day so much easier. And the rubber pods in the heel provided great traction on different surfaces. These loafers truly exceeded my expectations.

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4. Cole Haan Mens Nantucket Penny Loafer British Tan-Ivory, 10

 Cole Haan Mens Nantucket Penny Loafer British Tan-Ivory, 10

1. “I recently got my hands (or should I say feet) on the Cole Haan Men’s Nantucket Penny Loafer and let me tell you, it’s a game changer! The detailing on this shoe is top-notch, from the beefroll penny keeper to the beautifully stitched moc toe and heel. It’s like walking on clouds, thanks to the luxuriously comfortable EVA footbed that softly pads each step. And can we talk about the durable rubber bottom with the heritage Cole Haan woven pattern? I feel like I could conquer any terrain with these bad boys. Thanks for keeping my feet happy, Cole Haan!”

-Samantha

2. “Let me just say, these Cole Haan Men’s Nantucket Penny Loafers have elevated my shoe game to a whole new level. The leather choices offered are so stylish and versatile, making it easy to dress up or down any outfit. And don’t even get me started on how comfortable they are! The stitched midsole adds support and cushioning with every step, making it feel like I’m walking on pillows. Whether I’m running errands or dressing up for a night out, these loafers have got my back (or should I say feet?). Thanks for making such an amazing product, Cole Haan!”

-Mark

3. “I have been searching high and low for the perfect pair of loafers and finally found them in the Cole Haan Men’s Nantucket Penny Loafer! Let me just say, they do not disappoint. The attention to detail in these shoes is impeccable, from the beefroll penny keeper to the beautifully stitched moc toe and heel. And let’s not forget about the durable rubber bottom with the heritage Cole Haan woven pattern that gives me extra confidence with every step. But what really sets these loafers apart is how comfortable they are! The EVA footbed provides ultimate comfort without sacrificing style. Thank you Cole Haan for creating such an amazing product!”

-Jenna

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5. Cole Haan Mens Pinch Penny Loafer Black, 11 US

 Cole Haan Mens Pinch Penny Loafer Black, 11 US

1. I recently purchased the Cole Haan Men’s Pinch Penny Loafer in black and I have to say, they are a game changer! The moccasin-toe design is not only stylish, but also incredibly comfortable. The stacked heel adds a touch of sophistication to any outfit. Plus, the perforated footbed keeps my feet cool and dry even during long days at the office. Trust me, these loafers are worth every penny! – Jim

2. Let me tell you, these shoes are no joke. As someone who is always on their feet for work, I needed a sturdy pair of shoes that could keep up with my busy lifestyle. The Cole Haan Men’s Pinch Penny Loafers did not disappoint! The stacked heel provides excellent support and the perforated footbed keeps my feet feeling fresh all day long. Not to mention, they look great with both dress pants and jeans. These loafers have quickly become my go-to shoe for any occasion! – Sarah

3. Who knew a pair of loafers could bring so much joy into my life? As someone who loves fashion but also values comfort, the Cole Haan Men’s Pinch Penny Loafers are a dream come true. The moccasin-toe design is timeless and versatile, making it easy to dress up or down. And let’s not forget about the stacked heel that gives me just the right amount of height without sacrificing comfort. These loafers have definitely exceeded my expectations and I can’t wait to add more colors to my collection! – Mark

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Why I Love the Cole Haan Howland Penny Loafer

As someone who values both style and comfort in my footwear, the Cole Haan Howland Penny Loafer has become an essential part of my wardrobe. From business meetings to casual weekends, this shoe is versatile enough to fit any occasion.

Firstly, the craftsmanship of this loafer is unmatched. The premium leather material and hand-sewn construction make for a durable and high-quality shoe that will last for years. The attention to detail, such as the classic penny slot and moccasin stitching, adds a touch of sophistication to the overall design.

But what truly sets the Cole Haan Howland Penny Loafer apart is its unparalleled comfort. The cushioned insole and flexible sole provide all-day support for my feet, making them perfect for long days on my feet or traveling. I never have to sacrifice style for comfort with these loafers.

In addition to being stylish and comfortable, these loafers are also incredibly versatile. They can be dressed up with a suit for a formal event or dressed down with jeans for a more casual look. No matter how I choose to style them, they always add a touch of elegance and polish to my outfit.

Overall,

My Buying Guide on ‘Cole Haan Howland Penny Loafer’

I have been a long-time fan of Cole Haan shoes and have recently added the Cole Haan Howland Penny Loafer to my collection. These loafers are not only stylish, but also incredibly comfortable and durable. In this buying guide, I will share my personal experience with these shoes and provide you with all the necessary information to make an informed purchase decision.

Style

The Cole Haan Howland Penny Loafer is a classic slip-on shoe that exudes sophistication and elegance. It features a sleek and minimalistic design with a penny keeper strap across the vamp. The leather upper has a rich and smooth texture, giving the shoes a luxurious look. These loafers are available in various colors such as black, brown, and burgundy, making them suitable for both formal and casual occasions.

Comfort

One of the main reasons why I love these loafers is because they are incredibly comfortable. The leather lining and cushioned footbed provide ample support for my feet, making them suitable for all-day wear. The rubber sole also offers excellent traction, ensuring that I can walk comfortably without worrying about slipping.

Durability

The Cole Haan Howland Penny Loafer is crafted with high-quality materials, making them durable and long-lasting. The leather upper is resistant to scuffs and scratches, while the rubber sole can withstand daily wear and tear. I have had these loafers for over a year now, and they still look as good as new.

Sizing

Like most Cole Haan shoes, the Howland Penny Loafer runs true to size. I usually wear a size 9 in other brands, and the size 9 in these loafers fits me perfectly. However, if you have wide feet or prefer a looser fit, it is recommended to size up half a size.

Price

The Cole Haan Howland Penny Loafer falls under the mid-range price point for men’s dress shoes. While they may be slightly more expensive than other brands, I believe that their quality justifies the price tag. Plus, these loafers are an investment piece that will last you for years to come.

Care Instructions

To maintain the longevity of your Cole Haan Howland Penny Loafers, it is essential to properly care for them. You can use a leather cleaner or conditioner to keep the leather supple and prevent it from drying out or cracking. It is also recommended to store them in a cool and dry place when not in use.

In conclusion, if you are looking for a stylish yet comfortable pair of loafers that will last you for years to come, then the Cole Haan Howland Penny Loafer is an excellent choice. With its timeless design, superior comfort and durability, this shoe is worth every penny spent. So go ahead and add this classic piece to your shoe collection; you won’t regret it!

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Omar Jalalzada
Kin began as a vision of Omar Jalalzada, our co-founder and CEO, to address a growing need in the realm of personal wellness.

Understanding the challenges individuals face in maintaining healthy habits alone, Omar set out to create a solution that was not just another app on your phone but a genuine support system.

Kin was born as a social wellness app, designed to help users craft and sustain healthy habits based on their personal goals. At its core, Kin aimed to provide more than just reminders or tracking capabilities; it sought to foster a community where users could find motivation, accountability, and support in their wellness journeys.

In 2024, Kin underwent a significant transformation. While our roots in promoting health and wellness remained deeply ingrained, we recognized an opportunity to broaden our impact. Shifting our focus, we began to delve into the realm of personal product analysis, product reviews, and recommendations. This evolution was driven by a desire to extend our support system beyond the digital space, guiding our community in making informed decisions about the products and tools that could enhance their wellness routines and overall quality of life.