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Best Men’s Chunky Loafers

When I told my Dad I was looking for a good pair of Penny Loafers, he was surprised and confused. He said he used to wear them all the time when he worked in an office in the 1970s and 80s. Some of the pairs he had were very high quality, think Ferragamo loafers. But unfortunately for me (since we are the same size) he got rid of them many years ago. 

Why do you even want them? He asked me. 

It’s a valid question. I’m approaching 30 and am generally getting tired of the hype culture around sneakers. And Nike/Jordan is constantly raising their prices to the point where it becomes ridiculous to pay $200 for subpar quality. So as far as footwear goes, I thought loafers would be a good step for the spring to fall when boots feel a bit overkill. 

But not just any loafers. I wanted loafers that could be dressed up or down. A pair that still gives the comfort and aesthetic that a nice pair of sneakers do. Fortunately, I realized that chunky loafers which women have been wearing for decades, are now crossing into men’s fashion. 

But why is a chunky sole appealing to me. Generally, these chunky soles are rubber soles, specifically lug soles. Lug soles are traditionally used in workwear footwear for their grip/traction. But the look it gives a loafer, is simply flattering.

So you’re interested in chunky loafers. Now what?

Buying loafers can be a pain. The sizing is not the same as sneakers, I wear a 10 in Jordan 1 lows, but in loafers, I am usually a 9. But with loafers the brand variability in sizing is quite high. For luxury brands, I can be as low as an 8, and for more narrow cuts I can go up to a 9.5. There unfortunately is a lot of trial and error, and you may need to return a few pairs to get the sizing just right. You definitely don’t want the loafer to be too big as your heel will constantly pop out. I prefer a very snug fit, but the material will need to have some give. 

Some tips to keep in mind:

  1. Loafers can be worn with or without socks. A very snug fit with socks is preferred if you plan to wear them often without socks. 
  2. 100% leather has more give than synthetic materials. Leather will mold to your feet and the snug feeling will dissipate over time. 
  3. Generally, loafers with a moccasin toe have a wider footbed so they are naturally wide compared to dress shoes or some sneakers. If you think you have a wide foot, just be careful if you’re considering wide or super-wide sizing.

So you’re ready to go out and find a nice pair of loafers…

Brands like Clarks and Steve Madden don’t use the highest quality materials. But a main benefit is that they are available in many malls across the country. Therefore, we’ve included them at the top of the list, since they are beginner-friendly for people trying to get the right size. Some of these brands are online only, so we recommend contacting their customer service teams to find the correct sizing.

Clarks Badell

Introducing the Badell Step: the quintessential loafer that redefines smart-casual dressing for year-round elegance. Drawing inspiration from the timeless preppy style, this footwear masterpiece marries classic Clarks heritage with the modernity of an oversized EXTRALIGHT® sole. Crafted with a luxurious nubuck upper in a versatile black, it’s the epitome of wearable sophistication. At its heart, the groundbreaking Contour Cushion footbed promises unparalleled comfort with every stride, ensuring you’re stylishly equipped for wherever your adventures lead.

Price: $130

Where to buy: Clarks

Steve Madden Centro Black Leather

A fusion of boldness, modernity, and dynamic design. This loafer reimagines the classic penny silhouette with an audacious twist, featuring chunky squared treads that command attention and elevate the look with a boosted platform.

Price: $159.95 (Sale price: $109.97)

Where to buy: Steve Madden

Vagabond Cameron

Cameron is a nod to traditional elegance while firmly planted in contemporary style. It features a rounded toe shape, intricate moc-toe detailing, and the timeless penny slot adorning the vamp.

Price: $200

Where to buy: Vagabond

Velasca Milano Baüscia

The Baüscia is a testament to timeless craftsmanship and enduring style, brought to life with the renowned Vibram Lug Sole. Crafted by Velasca, an emblem of Italian high-quality footwear, Baüscia is a declaration of artisanal excellence.

Brent Fiore did an amazing review on this model

Price: $360

Where to buy: Velasca

Camper Walden

Walden’s aesthetic is deeply inspired by the beauty of nature and the pursuit of simplicity. Crafted from premium materials to ensure the highest quality, each piece is designed with unparalleled comfort in mind.

Price: $199

Where to buy: Camper

Johnston & Murphy Baldwin

The Baldwin Lug Sole Penny Loafer features handsewn moccasin construction and artisan-stitched detailing for timeless elegance. It’s equipped with a leather-covered cushioned footbed and an XL Extralight® high-abrasion EVA lug sole, ensuring both unparalleled comfort and durability.

Price: $195

Where to by: Zappos or Johnston & Murphy

G.H. Bass Larson Weejuns

The Larson Super Lug penny loafer combines effortless chic with unmatched comfort, making it the ultimate statement shoe. Its chunky super lug sole not only adds height but also ensures enhanced comfort and distinctive flair. Expertly crafted in El Salvador, this classic loafer features traditional moc stitching, positioning it as a fresh essential for your wardrobe.

Price: $175

Where to buy: G.H. Bass

Sebago Dan Lug

Price: $250

Where to buy: Sebago

Dr. Martens Adrian

Price: $150

Where to buy: Dr. Martens

Hugo Black Contrast Loafers

Price: $265

Where to buy: SSENSE

Vinny’s Richee

Price: $370

Where to buy: Vinny’s

ADIEU Type 182 Loafers

Price: $460

Where to buy: SSENSE

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