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25 Best Penny Loafers For Men

Best Penny Loafers Men

With a name as demure as ‘penny,’ you’d expect the shoe to be cheap in cost and construction. Contrary to popular belief, its money moniker tells an ancient tale of payphones rather than shoddy craftsmanship. 

In the 1930s, people had to manually pay for extra call time using coins. This type of shoe offered a discreet and convenient spot to store a single cent—and so, the penny loafer was born. 

Over the years, the penny loafer quickly evolved from a convenient cash storage spot into a symbol of Ivy league finesse. Its vintage silhouette paired with its collegiate design blends well with various core aesthetics, which include traditional formalwear and academia. 

If the 1930s vintage, classy style speaks to you, then perhaps it’s time to purchase a pair of penny loafers for men. I’ve gathered 25 of the best designs that are sure to cater to your inner gentleman. 

What Makes A Good Pair Of Penny Loafers For Men? 

Like any pair of shoes, there are four things to consider when shopping for penny loafers: fit, design, material quality, and comfort.

In terms of the materials used, brands utilize a common blend of leather and suede. Sturdy in construction, a well-made pair should last for years of use. 

It’s worth noting that these two textiles are quite stiff in nature, but they’ll slowly conform to the shape of your foot if they’re regularly worn. Of course, this doesn’t mean you should suffer from blisters and sore feet if the fit isn’t exactly on-point. 

There are thousands of penny loafers for men on the market. So there are several designs to choose from, including those with different colors, silhouettes, and embellishments. If you’re looking to cop a pair, it’s important to find loafers that align with your current aesthetic

Finding The Best Penny Loafers For Men 

Online shopping has its disadvantages. For one, it doesn’t come with the convenience of in-person try-ons.

If you’re looking to invest in a $500 pair of loafers, I recommend visiting a shoe boutique to get a sense of how they fit. Trust me, there’s nothing more annoying than dealing with time-sensitive return policies. 

Obviously, finding the best penny loafers for men depends on your current aesthetic. For instance, do you prefer traditional black or creamy beige?

With thousands of expensive designs to choose from, to make sure they choose the right pair, it’s imperative that customers sit back and think before heading to checkout. 

The 25 Best Penny Loafers For Men

Shopping for a special event? If not, no worries. Penny loafers for men are one of the most versatile shoes on the market. They aren’t exclusive to formal wear, as they can be donned on any occasion.

Whether they’re paired with jeans, chinos, or an elegant pair of tuxedo pants, I’ll share some of the best designs for trendsetters to consider. 

#1: Eastland Patricia Penny Loafer Driving Moc



Brand: Eastland
Retailer: QVC
Price: $90
Color:

Hit the road in comfortable style when you slip on the Patricia driving moccasin, with a rich leather upper and an insole that keeps feet happy mile after mile. From Eastland.


#2: Santoni Pet Penny Loafer in Dk Brown



Brand: Santoni
Retailer: Nordstrom
Price: $650
Color: Dk Brown

Elevate your business-casual look with this refined Italian-crafted penny loafer made of soft, burnished calfskin leather and set on a flexible rubber sole. Leather upper and lining/rubber sole Made in Italy


#3: Donald Pliner Casual Penny Loafer in Denim



Brand: Donald Pliner
Retailer: Nordstrom
Price: $265
Color: Denim

Hardy canvas is surrounded by gentle suede accents on this casual-cool loafer boasting plush memory foam cushioning and a lightweight sole. Memory foam cushioning Textile and leather upper/leather lining/rubber sole Made in Italy


#4: Cole Haan GrandPro Ralley Penny Loafer in Riverstone Suede/Birch



Brand: Cole Haan
Retailer: Nordstrom
Price: $140
Color: Riverstone Suede/ Birch

A breathable OrthoLite(R) footbed adds cushioned comfort to a sporty loafer pairing a velvety suede upper with a sneaker-inspired rubber sole. OrthoLite footbed Leather upper/textile lining/rubber sole Imported


#5: Sandro Moscoloni Jayson Penny Loafer in Brown



Brand: Sandro Moscoloni
Retailer: Nordstrom
Price: $112
Color: Brown

Richly textured leather defines a smart Spanish loafer in a clean, classic silhouette. Leather upper, lining and sole Made in Spain Men's Shoes


#6: Cole Haan GrandPro Ralley Penny Loafer in Black Suede/Mortar



Brand: Cole Haan
Retailer: Nordstrom
Price: $140
Color: Black Suede/ Mortar

A breathable OrthoLite(R) footbed adds cushioned comfort to a sporty loafer pairing a velvety suede upper with a sneaker-inspired rubber sole. OrthoLite footbed Leather upper/textile lining/rubber sole Imported


#7: Rockport Keaton Penny Loafer in Black



Brand: Rockport
Retailer: Nordstrom
Price: $115
Color: Black

A moisture-wicking lining keeps feet cool in this classic leather penny loafer cushioned with a shock absorbing footbed. Leather upper/textile lining/synthetic sole Imported


#8: Steve Madden Levon Penny Loafer in Cognac Suede



Brand: Steve Madden
Retailer: Nordstrom
Price: $94
Color:

A clean, classic silhouette defines a charming loafer fashioned from creamy suede. Unlined Leather upper/rubber sole Imported Men's Shoes


#9: Salvatore Ferragamo Lord Penny Loafer in Nero Nude Espresso



Brand: Salvatore Ferragamo
Retailer: Nordstrom
Price: $850
Color: Nero Nude Espresso

Impeccable Ferragamo craftmanship shines though on this suave penny loafer made of burnished calfskin leather and outlined with tonal topstitching. Leather upper, lining and sole Made in Italy Men's Designer Shoes


#10: VINNYS Townee Penny Loafer in Brown



Brand: VINNYS
Retailer: Nordstrom
Price: $349
Color: Brown

Smooth calfskin leather shapes this classic penny loafer featuring a soft, comfort-focused footbed. Leather upper, lining and sole Imported


#11: Prada Saffiano Leather Penny Loafer in Black



Brand: Prada
Retailer: Nordstrom
Price: $775
Color: Black

Etched Saffiano leather marks a rich Italian penny loafer crafted with a slim, refined profile. Leather upper and lining/rubber sole Made in Italy Men's Shoes


#12: Swims Breeze Hybrid Penny Loafer in Brown



Brand: Swims
Retailer: Nordstrom
Price: $268
Color: Brown

Stay light on your feet with this city-ready loafer featuring bubble cushioning and a grippy traction sole. Textile and leather upper and lining/synthetic sole Imported


#13: Swims Breeze Hybrid Penny Loafer in Black



Brand: Swims
Retailer: Nordstrom
Price: $268
Color: Black

Stay light on your feet with this city-ready loafer featuring bubble cushioning and a grippy traction sole. Textile and leather upper and lining/synthetic sole Imported


#14: Swims Washable Penny Loafer in Brown Fabric



Brand: Swims
Retailer: Nordstrom
Price: $160
Color: Brown Fabric

Breathable ventilation gills punctuate the sides of a machine-washable penny loafer lined with lightweight mesh and set on a classic segmented driver sole. Removable cushioned insole Textile and synthetic upper and lining/rubber sole Machine washable Imported Men's Shoes


#15: Johnston & Murphy Melton Penny Loafer in Tan Calfskin



Brand: Johnston & Murphy
Retailer: Nordstrom
Price: $179
Color: Tan Calfskin

Sleek full-grain leather elevates this slip-on penny loafer expertly welted to a lightweight leather sole. Memory foam cushioning Leather upper, lining and sole Imported


#16: J AND M COLLECTION Johnston & Murphy Baldwin Penny Loafer in Snuff



Brand: J AND M COLLECTION
Retailer: Nordstrom
Price: $195
Color: Snuff

Waxed English suede enriches a classic penny loafer with a smart memory-foam footbed for all-day support. Leather upper and lining/rubber sole Imported Men's Shoes


#17: Tod's Croc Embossed Penny Loafer in Burgundy



Brand: Tod's
Retailer: Nordstrom
Price: $172
Color: Burgundy

Croc-embossing richly textures an Italian-crafted penny loafer with classic detailing, from moc-stitching at the toe to a leather welt at the heel. 1 1/4" (31mm) heel; 3/4" platform (size 38.5) Leather upper and lining/synthetic sole Made in Italy Women's Designer Shoes


#18: Cole Haan Grand Ambition Penny Loafer in Navy Ink



Brand: Cole Haan
Retailer: Nordstrom
Price: $150
Color: Navy Ink

Cushioned with GrandOS energy foam, this penny loafer crafted from smooth leather brings easy comfort to your casual and work looks. Cushioned footbed Leather upper/textile and leather lining/rubber sole Imported


#19: Italeau Luciana Waterproof Penny Loafer in Nut



Brand: Italeau
Retailer: Nordstrom
Price: $245
Color:

A contoured penny strap and sleek apron toe bring timeless detailing to a loafer crafted from waterproofed leather that stands up to puddles and stains. An elastic-inset topline keeps the fit comfortable, while the grippy rubber tread puts traction underfoot on wet or dry surfaces. Waterproof: protects against rain, puddles and slush to keep your feet dry in wet conditions Support: enhances the fit with targeted contouring and cushioning in the


#20: Kelsi Dagger Brooklyn Lens Penny Loafer in Coconut



Brand: Kelsi Dagger Brooklyn
Retailer: Nordstrom
Price: $130
Color: Coconut

Crochet detailing at the vamp and a classic penny keeper lend contemporary dimension to a sophisticated loafer set on a mini stacked heel. Leather and textile upper/textile lining/recycled rubber sole Imported


#21: Kelsi Dagger Brooklyn Lens Penny Loafer in Spice



Brand: Kelsi Dagger Brooklyn
Retailer: Nordstrom
Price: $130
Color: Spice

A supple suede finish and classic penny keeper lend contemporary sophistication to a luxe loafer set on a mini stacked heel. Leather upper/textile lining/recycled rubber sole Imported


#22: Steve Madden Normin Canvas Penny Loafer in Navy Fabric



Brand: Steve Madden
Retailer: Nordstrom
Price: $80
Color: Navy Fabric

A dapper mix of canvas and suede brings laid-back vintage vibes to a penny loafer that's right at home from boat shows to garden parties. Textile and leather upper/textile lining/rubber sole Imported


#23: Pas de Rouge Classic Penny Loafer in Black Patent Leather



Brand: Pas de Rouge
Retailer: Nordstrom
Price: $320
Color: Black Patent Leather

A classic penny loafer crafted in Italy is supported with a lightweight lugged sole and detailed with red stitching at the keeper and a bold red lining. 1 1/4" heel (size 39EU) Patent leather upper and lining/synthetic sole Made in Italy Women's Shoes


#24: Santoni Doting Penny Loafer in Dark Brown



Brand: Santoni
Retailer: Nordstrom
Price: $1350
Color: Dark Brown

A classic penny loafer is updated with an intricately woven profile that lends texture to your formal ensembles. Leather upper, lining and sole Made in Italy


#25: Burberry Broadbrook Check Penny Loafer in Archive Beige Chk



Brand: Burberry
Retailer: Nordstrom
Price: $770
Color: Archive Beige Chk

Durable nylon is woven with the iconic exploded check pattern in this runway-featured penny loafer topped with engraved hardware. 1" (25mm) heel (size 38.5) Textile upper/leather lining and sole Made in Italy Women's Designer Shoes


What Are The Most Popular Penny Loafers For Men?

From department store brands to designer styles, the market for penny loafers continues to grow every year. We’re spoiled with countless options, which doesn’t bode well for the novice dresser who frequently experiences shopping frustration.

To keep things clear and concise, I’ll share some of the most popular penny loafers for men on my shortlist. 

  • The Jack Erwin Carmine Penny Loafer 
  • The Sanders Edwin Penny Loafer 
  • The To Boot New York Berle Leather Penny Loafer 
  • The Sperry Gold Cup Cabo PLUSHWAVE Penny Loafer 

Do Penny Loafers For Men Run Big Or Small?

According to some customers online, penny loafers for men tend to run a little big. So most of them advise purchasing a half-a-size down to ensure an optimal fit.

Of course, sizes may vary from brand to brand. As a result, it’s best to reference the company’s measurements chart before purchasing a pair. 

Are Penny Loafers Comfortable?

Penny loafers offer a commendable degree of comfort, as long as they’re worn appropriately. Hiking, long city walks, and other high-performance activities require additional support, as formal shoes are usually designed specifically for special events. 

It’s worth noting that some penny loafers for men feature orthopedic inserts, which is great for those who suffer from foot pain.

How To Style Penny Loafers For Men

Penny loafers are the literal embodiment of sophistication. If you want to exude style and class, perhaps it’s time to cop a pair. For those in need of fashion tips, I’ll show you how to wear penny loafers for men. 

Suit trousers aren’t the most wearable pair of pants. If you’re looking to wear your penny loafers out more often, I suggest swapping your trousers with camo bottoms.

Ideally worn with matching socks, this streetwear look offers a blend of modern finesse with vintage academia. 

Featuring a white long-sleeve top, a pair of tweed pants, and some black penny loafers, this stylish look strikes an even balance between streetwear edge and contemporary class

Floral button-downs are the best way to jazz up an outfit. But, if it’s too cheesy for your liking, I suggest mellowing it down with black pants and a pair of espresso penny loafers. 


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