Dean | Men's Chunky Leather Penny Loafers
Dean | Men's Chunky Leather Penny Loafers
Dean | Men's Chunky Leather Penny Loafers
Dean | Men's Chunky Leather Penny Loafers
Dean | Men's Chunky Leather Penny Loafers
Dean | Men's Chunky Leather Penny Loafers
Dean | Men's Chunky Leather Penny Loafers
Dean | Men's Chunky Leather Penny Loafers
Linda T.
Linda T. verified and 35,000+ others love our clothing

Dean | Men's Chunky Leather Penny Loafers

$190.00 $94.95 Save $95.05
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UPDATE: Limited Stock Alert! 5 pieces available due to high demand during the SALE. If you can still click "Add to Cart," it is still available.

Timeless Style, Modern Comfort

Step into versatile sophistication with the Dean Men's Chunky Leather Penny Loafers, a pair of chunky slip-on shoes that blend classic design with everyday ease. These penny loafers feature a rich leather upper, a comfortable moccasin-style toe, and a distinctive horizontal strap for timeless appeal. Built with soft, waterproof leather and a thick non-slip rubber sole, they offer durable comfort and reliable traction for all-day wear.

Why You'll Love It

  • Easy Slip-On Design: The classic loafer style allows for quick, hassle-free wear while maintaining a polished, put-together look.

  • Comfortable & Breathable Leather: The high-quality soft leather molds to your foot over time, providing a comfortable, breathable fit that stays fresh.

  • Durable & Secure Grip: The thick rubber sole offers excellent wear resistance, flexibility, and non-slip traction on various surfaces.

  • Versatile Smart-Casual Style: These loafers pair effortlessly with jeans, chinos, or tailored trousers, making them suitable for both casual outings and dressed-up occasions.

Add reliable comfort and enduring style to your footwear collection—get the Dean Loafers today

We offer FREE USPS Shipping on all orders shipped within the United States.
Check our Shipping Policy for more

We’re confident you’ll love your purchase — but if it’s not quite right, you have 90 days to return it for a full refund.

Read our full Return and Refund Policy

Customer Services Hours:
Monday to Saturday: 9:00 AM – 6:00 PM EST

Email: support@orion-newyork.com
Phone:+1 302 612 0409
Contact Form: Available online on our Contact Us page

Loved by Customers Across the U.S.

Helen P.

Looks better in real life

I was a bit unsure ordering online, but it actually looks better than the photos. The fit is flattering and the fabric feels really nice.
Helen P.
Marianne L.

Warm without feeling bulky

Very comfortable to wear and surprisingly warm. I like that it doesn’t feel heavy or stiff. I’ve worn it almost every day since it arrived.
Marianne L.
Michael H.

Warm and looks good

Wore this during cold morning walks and it keeps me warm without feeling heavy. The fit is comfortable and still looks neat. I like clothing that feels natural to wear!
Michael H.
Susan M.

Easy to style

It goes with almost everything I already own. Jeans, boots, scarf, it just works. I like clothing that doesn’t need much thinking.
Susan M.
Carol W.

Just feels right

From the moment I put on this dress it felt right. Not stiff, not too loose. I’ve had a few compliments already which is always nice.
Carol W.
Robert K.

Perfect for winter walks

Bought this for everyday use and I’m very happy with it. Keeps me warm on walks and still looks neat enough to wear into town. Would buy again.
Robert K.
Laura S.

Perfect summer dress

Such a nice dress for warm days. The fabric feels light and comfortable and it fits really well. I wore it on holiday and felt dressed up without trying too hard
Laura S.
Elaine T.

Warm and flattering

Very happy with this purchase. The cut is flattering without being tight and it feels soft on the skin. Definitely recommend.
Elaine T.
Denise W.

Easy and flattering

I’m very happy with this dress. It’s easy to wear, not tight, and very flattering. Got a few compliments the first day I wore it. Will probably order another color.
Denise W.

Where It Began

Orion New York began long before it became a brand.

In a small workshop, their grandmother Margaret Orion spent years creating garments focused on comfort, fit, and longevity. For her, clothing was never about trends, but about how it felt throughout the day and how long it truly lasted.

Those values became the foundation of Orion.

A New Generation

Years later, siblings Elena and Marcus Orion carried those principles forward. They refined them for today, with modern silhouettes, thoughtful materials, and a clear focus on wearability.

Clothing was never about trends, but about how it felt, how it moved, and how long it lasted. Those values became the foundation of Orion.

Craft, Comfort, and Continuity

Orion New York stands for quiet quality. Carefully selected fabrics. Considered construction. Pieces made to be worn often, trusted daily, and appreciated over time.

This is clothing shaped by experience. Built to last. Designed to feel right from the first wear, and even better as time goes on.

COMBINE & GET EXTRA % OFF!

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Behind the scenes

CRAFTED BY EXPERIENCE

Every piece is shaped with experience, patience, and respect for the craft. From the first cut to the final stitch, nothing is rushed. This is clothing made with intention, designed to feel right, wear well, and last over time.

In a world of mass production, choose something real.

Free Shipping

We offer FREE USPS Shipping on all orders shipped within the United States.

Shipping Policy

90-Day Money Back Guarantee

You can request a return or refund within 90 days of delivery.

Return and Refund Policy

Customer Service

Customer Services Hours:
Monday to Saturday: 9:00 AM – 6:00 PM EST

Contact Us