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7 Best Men’s Loafers That Are Comfortable & Look Terrific

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There’s nothing quite like a quality pair of loafers and what they can add to a man’s wardrobe. The loafer is versatile enough to be worn in a variety of settings and occasions, but also more comfortable than a lot of other footwear.

We’re here to take a look at the best loafers for men in 2019, including our No. 1 pick, the Cole Haan’s Men’s Howland Penny Loafer as well as things to look for when buying loafers, the different types of loafers, and how to wear loafers in way that enhance a man’s overall look. 

First, some buying tips.

CONTENTS:

Before You Buy: 5 Things to Consider When Purchasing Loafers

One thing you won’t have to worry about when buying loafers is having enough choices. From style, to the material, to color, to brand name – you shouldn’t have much problem finding a loafer that suits you, fits your foot, and is appropriate for the occasion.

1. Fit

There’s a reason we list fit first among things you should consider when purchasing loafers. The fit is everything, no matter what type of shoe you buy, and wearing a loafer that’s the wrong size – even just slightly the wrong size – isn’t going to make you or your feet happy.

Some important factors to consider when finding the right fit include having your feet sized by a professional whenever possible. This obviously entails buying shoes from a retail outlet, but it’s something you should do every time you visit a shoe store.

In many cases, the size may vary between each of your feet. Also, the size of your feet can change as you get older, because they flatten over time because of a loss of elasticity in tendons and ligaments.

Here’s something else: a shoe’s fit often varies by the time of day; a person’s feet naturally swell throughout the day and a shoe that fits snug in the morning may fit too tightly in the evening. That said, it’s best to try on shoes in the late afternoon or early evening when you’ll get a more “true” fit.

A shoe’s fit often varies from brand to brand, as well. For instance, a size 8 penny loafer from one manufacturer may fit entirely different than a size 8 constructed by another company.

You may or may not wear socks with your loafers (or you may choose to do both) and whatever option you choose affects the fit. If you do plan to wear socks, bring a pair with you for trying on shoes.

Buying shoes online can be something of a gamble for getting the right fit, but knowing the true measurement of your feet, consulting the size guide often included on a product’s web page, and reading the reviews of others will help alleviate much of the guesswork.

2. Occasion

Consider the occasions in which you’ll wear your loafers – what’s their function? Are you going to wear a suit? Will you wear them on a semi-casual date, or for a night of hanging out with friends? Many men also choose to wear loafers with shorts. We’ll talk more about pairing loafers with the proper clothes later on, but for now know that how you plan to wear them is an important consideration when buying loafers.

3. Material

Most loafers come in leather or suede. Both types of material have their strengths and weaknesses and can affect your overall look. Leather loafers have a sleek, gleaming finish that works well with smarter looks (such as with a suit), while suede works best for spring and summer wear. Suede shoes tend to have more of a casual feel than leather loafers, but that doesn’t mean you can’t wear them with more formal clothing.

Not to confuse, but suede is a type of leather. The difference is that suede comes from the underside of animal skin and regular leather from the outer side. Suede has a velvety, matte finish that’s softer than regular leather.

If you need a loafer for formal occasions, then check out those made from patent leather – a type of coated leather with a high-gloss finish.

4. Color

Black and brown are the classic loafer colors but loafers cover a wide color palette. Navy is another color to consider, while burgundy is favorite of many wearers who like its versatility and how it brightens a wardrobe. Neutral colors, such as beige, help to complement a nice suntan.

5. Type

Penny loafers, tasseled loafers, horsebit loafers – all are types of loafers you may buy. We’ll cover each type in a bit more detail later.

Let’s move on to our reviews of the best loafers for men in 2019.

The 7 Best Loafers For Men 2019

1. Cole Haan Men’s Howland Penny Loafer

Cole Haan Men's Howland Penny Loafer

“Upscale” is a word that gets tossed around a lot when describing Cole Haan’s line of footwear. Or, as the company itself puts it, Cole Haan “caters to the well-heeled.” So be it.

No matter how you attempt to describe Cole Haan’s line of shoes, including its men’s Howland Penny Loafer, it comes down to quality – and CH has a strong reputation for developing stylish, comfortable shoes that fit a variety of occasions.

The Howland Penny Loafer is often referred to as a perennially “preppy” favorite, although it by no means is restricted only for prepster use. Any man can enhance their casual to semi-casual wardrobe with a pair of Howland penny loafers thanks to their timeless style that features a vintage leather finish.

The Howland comes with a traditional monk strap and penny slot and features classic moccasin stitching and a split-pod sole. In a split-pod sole, support is most dense in the front of the shoe; the front part of the sole is separate from the heel.

It also comes with perforated arch support, as well as a calfskin upper. The heel is considered a “driving” shoe in that it provides maximum grip when you press on the accelerator or brake. No matter how you use and wear it, however, it has a sophisticated style that looks good in almost every setting.

Reviewers like the overall classiness of the Howland, with some referring to it as a “dress” shoe and others remarking how well they fit narrower feet. No matter how you characterize it, however, we think it rates at the top of a list of the best penny loafers.

Pros

  • Classic penny loafer design
  • Suitable for wear during most occasions
  • Sole provides firm grip and traction

Cons

  • May need some time to break in

Bottom Line

The Howland is a cut above most other penny loafers and features a classic look that will serve you well for a wide range of work and casual outings. It’s yet another strong product from Cole Haan.

2. Dockers Men’s Sinclair Leather Casual Tassel Loafer

Dockers Men’s Sinclair Leather Casual Tassel Loafer

Dockers built its reputation at the beginning of its now-iconic khaki pants, but many customers also choose Dockers for footwear. Dockers shoes lean toward the casual, including their Sinclair Leather Tassel Loafer Shoe – although the latter is ideal for enhancing your work wardrobe.

Whether its pants or shoes, however, Dockers is known for comfort and the Sinclair is no exception. It features a cushioned footbed and microsuede cover to provide the ultimate in comfort and softness throughout the day.

There’s also a padded collar and insole to contribute further comfort, while the rubber outsole is durable and provides the right amount of traction and stability.

We also like its classic tassel loafer design and how it pairs well with a wide variety of wardrobe choices. You can wear the Sinclair with casual slacks, jeans, and – as you’d expect – khakis while creating a look that fits many occasions, including a work environment in which business casual is the norm. All in all, it’s a truly versatile loafer.

The Sinclair also comes at a reasonable price, which means you can create a smart, appropriate-for-the-occasion look without having to break the bank.

Pros

  • Elegant and versatile
  • Comfortable for all-day wear
  • Stylish design

Cons

  • Sizing may be difficult when buying online

Bottom Line

The Dockers Sinclair combines a stylish design with superior comfort to make it one of the best men’s casual loafers around. You can wear it with a variety of wardrobe choices and not feel a bit out of place.

3. ECCO Men’s Classic Moc 2.0 Slip-On Loafer

ECCO Men’s Classic Moc 2.0 Slip-On Loafer

A shoe’s overall comfort includes how it fits. Seems obvious enough, but some wearers sacrifice fit in choosing a shoe they fall in love with and then regret the decision after a few days of pinched toes and walking around gingerly.

ECCO is all about the fit and offers its unique Freedom Fit to back it up. Unlike conventional shoes, which ECCO say restrict the way a person’s toes spread when walking, the Freedom Fit feature offers a roomy toebox while fitting more narrowly from heel to instep. In turn, your toes spread naturally to support your weight and to create a more comfortable walking experience.

As the folks at ECCO put it, you should get a comfortable fit from the first time you try on your new shoes after pulling them from the box – including with their highly-popular Classic Moc 2.0 Slip-On Loafer.

ECCO is unique in a lot of ways, including that it’s one of the few footwear manufacturers that has its own tanneries, and where it processes its hides and leathers. Their tanneries use highly-advanced processes and treatments, and use vegetable-tanned leather in various stages of the shoe construction, including in its exclusive inlay sole.

ECCO places a soft layer of moisture absorbent foam under an inlay sole treated with Agion – an antimicrobial technology that controls bacteria and odor. The foam also has tiny holes in it in which air is pushed out during walking to create more comfortable circulation around the foot.

The Classic Moc 2.0 outsole consists of Polyurethane, which is said to last longer – perhaps two times longer – than traditional material. Its flexible and shock absorbing, and requires little breaking in, if at all.

ECCO also incorporates the Direct Inject Production process in its sole technology to help create the instant-fit quality of its shoes. DIP is a process in which the shoe’s upper is placed into a mold and injected with polyurethane to shape the midsole and outsole for anatomical correctness.

All of the above makes for a well-constructed, comfortable shoe, but the Classic Moc 2.0 also provides a sophisticated style that’s versatile enough to be worn with a variety of clothing. It has a rich leather look with a clean moccasin silhouette, but also – as mentioned – a breathable lining that keeps your foot cool, dry and comfortable throughout the day.

Pros

  • Freedom Fit construction
  • Anti-microbial technology helps control odor
  • Breathable lining

Cons

  • Sizing may run a bit large

Bottom Line

Anyone seeking a flexible, slip-on leather loafer should consider ECCO’s Moc 2.0. From fit to solid construction, it’s an excellent loafer in many ways.

4. Calvin Klein Men’s Magnus Slip-On Loafer

Calvin Klein Men’s Magnus Slip-On Loafer

Global lifestyle and apparel giant Calvin Klein earns a spot in our reviews of the best loafers brands with its Magnus Slip-On Loafer. We like it for a lot of reasons, including that it aptly meets CK’s reputation for innovative, striking designs.

Its design also makes it highly-versatile and suitable for casual weekend activities or when paired with work attire. Made from 100% leather, the Magnus Slip-On loafer comes in extended sizes and widths, which makes it easier to find a pair that fits your foot’s unique shape.

The Magnus design also includes a cushioned foam insole for superior comfort that makes them comfortable for all-day wear. It’s also a very flexible and gives your foot enough room to move comfortably, but not too much room that the fit is annoyingly loose.

The man-made outsoles look good and, most importantly, provide more than enough traction, stability, and shock absorption.

But, getting back to a previous point, one of the reasons we included this loafer on our list is its versatility. Whether you’re out on the town with friends or working in an office, the Magnus loafer is right for the occasion.

Pros

  • Flexible construction and comfortable fit
  • Versatile
  • Crafted with soft leather

Cons

  • Sizing may run small

Bottom Line

The Calvin Klein Magnus loafer is comfortable, classy-looking, and durable. You can wear it for a variety of occasions without sacrificing style.

5. Rockport Men’s Classic Lite Penny Loafer

Rockport Men’s Classic Lite Penny Loafer

It seems that the folks at Rockport are in a state of continuous dissatisfaction – but in a good way. It’s all because Rockport believes that the perfect shoe doesn’t exist, so they’ve made it their mission – through continuous research and new technology – to build one.

Rockport is moving in the right direction, and their Classic Lite Penny Loafer is proof, and that’s good news from a company that was the first to use advanced athletic technologies in casual shoes several decades ago.

Like other shoes in the Rockport line, the Classic Lite Penny Loafer provides lightweight comfort thanks to engineering that gives the shoe flex in all directions. You’ll like how your feet feel in these shoes, even if you spend long portions of your day on your feet.

The Classic Lite has a classic slip-on, penny loafer look, that’s appropriate for casual and business settings and pairs well with a lot of different wardrobe choices. You can wear it with socks or barefoot, and it has an air-blown outsole and unique lining that wicks away moisture to help keep your feet dry.

The Classic Lite’s polyurethane outsole serves as an excellent shock absorber while its footbed conforms to the shape of the wearer’s foot while offering a personalized fit and enhanced comfort.

Made of 100% leather, the Classic Lite also has a 1-inch heel. Overall, it’s a stable shoe that adapts ideally to regular walking and unexpected movements. The shoe comes in the classic brown color but you can also get it in black, cognac, and other hues.

Pros

  • Engineered for lightweight comfort
  • Versatile enough to wear for a variety of occasions
  • Lining wicks away moisture

Cons

  • May discolor if wet

Bottom Line

The Classic Lite Penny Loafer is a versatile shoe that you can wear comfortably in a variety of settings, and the emphasis is on comfort. It’s lightweight, stable, and keeps your feet from becoming overly fatigued.

6. JIONS Men’s Driving Suede Moccasins Slip-On Casual Shoes

JIONS Men’s Driving Suede Moccasins Slip-On Casual Shoes

 

There are plenty of options when it comes to suede loafers and we think JIONS Driving Penny Loafers are the best of the bunch. We like it for a lot of reasons, including a rubber-studded sole that delivers great foot-to-pedal sensitivity whether you’re driving on the open road or in a more urban environment.

It also has a stylish look and design that comes in several colors, including the go-to blue, and there’s more:

  • It’s constructed with handmade Italian stitching that includes excellent detailing both on the vamp and throughout the shoe.
  • Their slip-on design makes them easy to take on and off.
  • The EVA shock-proof insole is soft and helps ward off foot fatigue.
  • The studded sole is excellent for driving, as mentioned, but also provides needed stability and support when walking or standing.
  • It’s easy to pair the JIONS loafers with different types of clothing, whether they’re jeans, suits, shorts, khakis, etc. Besides blue, you can also buy them in khaki, grey, red, and black.
  • We also like the breathable and antimicrobial insole that keeps feet comfortable whether you’re driving or mingling with others at a social event.

Pros

  • Excellent for driving
  • Several color options
  • Handmade craftsmanship

Cons

  • Check sizing carefully

Bottom Line

The JIONS Suede Moccasin Slip-On is a great shoe to wear when you’re behind the wheel but look good in many different settings and for many occasions. They’re among the best suede loafers you can buy.

7. Cole Haan Men’s Pinch Tassel Loafer

Cole Haan Men’s Pinch Tassel Loafer

Another Cole Haan entry on our list is their Men’s Pinch Tassel Loafer, which helps uphold the company’s reputation for creating quality footwear that’s stylish and versatile. It also fits nicely into Cole Haan’s lineup of the best luxury men’s loafers.

There’s a lot to love about the Pinch Tassel Loafer, from its tasseled detailing – which is second to none – to its hand-sewn construction. You can wear them with socks, or without, thanks to their padded 100% leather lining that offers excellent comfort. It also has a stacked heel that measures approximately 1-inch, as well as a sole made of leather.

The shoe also features Cole Haan’s Grand/OS technology that utilizes cushioning foam for further comfort. All in all, it’s a well-crafted shoe that should give you plenty of use with the proper care.

Pros

  • Classic styling and design that follows Cole Haan tradition
  • Comfortable leather lining
  • Good for casual and formal wear

Cons

  • Sizing runs big

Bottom Line

With a luxury feel and design, the Cole Haan Pinch Tassel Loafer adds something extra to any man’s wardrobe without sacrificing comfort or durability.

6 Tips For Wearing Loafers With Class & Comfort

There’s a right way and wrong way to wear any clothing or footwear, loafers included. Some rules are obvious – you shouldn’t wear running shoes with a business suit, or steel-toed work boots to your daughter’s wedding – while others require a bit more fashion sense.

1. Wearing loafers for different occasions

Casual

It’s interesting what a pair of loafers, when used to replace running shoes or trainers, can do to spruce up a casual outfit. You don’t want to look overly dressed-up or formal for an occasion such as a backyard barbecue, but suedes and lightweight-textured loafers adapt easily to casual looks while adding a bit more style.

Semi-formal

Many loafers are versatile enough to give you a “dressier” look that’s more relaxed and simplistic than, say, an Oxford brogue or another type of traditional dress shoe. Some rules to follow when wearing loafer for semi-formal occasions include:

  • The tones of your clothes should be in the same color palette as your shoes.
  • Suede is a great option for workplaces in which the dress code isn’t as strict.
  • Loafers with brighter colors pair well with pants and shirts of more subdued tones, such as navy and white.
  • Classic colors provide an excellent complement to your staple trousers and shirts.
  • In general, loafers give you a dressier look than many other types of footwear and, for that reason, usually work well with more ambiguous dress codes.

Formal

Should you wear loafers for more formal occasions? Maybe not, but if you do, patent leather is your material of choice. Black patent leather is a timeless option and offers a classic look, although textured loafers will also stand out, but not an obnoxious way. A loafer made of high-quality velvet suede for instance, has a dressy look that adds a touch of luxury to your look.

The length of the pant leg is the most important factor when wearing loafers with a suit. There should be a slight break at the bottom that allows you to see the shoe’s detail and design.

2. To wear socks, or not wear socks – that is the question

Many men prefer to wear loafer without socks for many reasons. For one, it’s comfortable. For another, wearing socks with loafers may result in some curiously bad fashion choices, such as the calf-high sock, loafer, and shorts-look favored by the proverbial weird uncle at the annual family reunion.

If you decide to wear loafers sans socks, pants of shorter length will complement the loafer style better than trousers that hang over your ankle and beyond. On the other hand, going sockless while wearing loafers at a more formal occasion isn’t the wisest choice either, so choosing when to wear loafers, rather than a traditional dress shoe, is always an important consideration.

Thanks to no-show socks, you can even wear socks while maintaining the sockless look.

And, if your feet sweat a lot, sprinkle some talcum powder into the bottom of your loafers, or on your feet, every time you wear them.

3. How to wear different types of loafers

Penny loafers are a more casual choice of footwear but can add some vibrancy to your look that you won’t get with running shoes or sneakers. They pair well with denim, khakis, corduroys, or even with a linen suit in the summer. You can even wear them to complement that preppy blazer you like to pull from the closet now and again.

Tassel loafers rate slightly above penny loafers regarding formality, and many businessmen, particularly in the U.S., wear tassel loafers with business suits or sport coats and slacks. As a general rule, however, pair your tasseled loafers with casual suits and blazers.

Gucci loafers, or Gucci Horsebit loafers, which we’ll discuss in a bit, work well with a variety of outfits and represent are more formal than penny and tassel loafers. Still, a loafer is a loafer, and even a Gucci loafer isn’t the best choice of footwear for the classic three-piece business suit.

4. Loafers with jeans

Loafers pair well with jeans, but not jeans that are excessively long or baggy. The length of your jeans needs to be on the shorter side (why hide the look and design of your loafers?), while you can wear loafers and jeans of contrasting color as long as your shirt complements your lower half.

5. Loafers with shorts

There’s nothing wrong with wearing loafers with shorts but you can look like something of a geek if you don’t combine the look the right away. Your shorts should be tailored, for one, and reach to just above your knee, while you’ll also need a belt and a tailored shirt. Otherwise you risk appearing like too much of a preppy, which isn’t a good thing in most cases.

6. Loafers with a suit

Loafers do pair well with a suit but your pant length is, again, important. The proper trouser length when wearing loafers and a suit is to the ankle. It’s your choice whether to wear socks or not – and the sockless trend is nothing new – but consider the occasion and the weather before you leave your socks at home.

The Different Types of Loafers, Explained

A loafer is a loafer is a loafer, right? Not so fast. Loafers come in a variety of styles and designs, just like dress shoes, sneakers, casual shoes – you get the picture.

Penny Loafer

Many people think “penny loafer” when the subject of loafer styles comes up. It’s an iconic type of footwear with a history dating to the 19th century. The modern version, designed by a bootmaker in Maine in 1934, was initially called a “Weejun” and featured the now-distinctive strip of leather across the front with a diamond cutout – the compartment where you can stash a penny or a dime.

One of the many pluses of a penny loafer is its versatility; you can wear it with a variety of wardrobe styles (casual and more formal), and it’s a great option for summer wear, although it’s not limited by season.

Tassel Loafer

The Tassel loafer has an interesting history that includes an Oscar-winning actor, which not every shoe style can claim. Paul Lukas, a popular actor in the 1930s and 40s, asked several American shoemakers if they could design a variation of the tasseled Oxford shoe made in Europe.

The Alden Shoe Company, one of America’s leading shoemakers at the time, took the bait and subsequently released the first tasseled loafer in 1950. Soon, high-society apparel and footwear companies stocked their shelves with the new loafer style, which included distinctive raised stitching at the back of the shoe.

The definition of a tassel loafer is fairly simple: it’s a laceless shoe with decorative tassels typically made from the ends of leather laces hung from the shoe’s vamp. Many tassel loafers include a 360-degree lacing system and have a true loafer construction, i.e., a moccasin upper stitched to a separate sole and heel.

AurlandLoafer

“Aurland” refers to a town in Norway where its namesake loafer was introduced at the turn of the 20th century. An updated version, called the “Aurland moccasin,” included heels and hit the market in 1930.

No matter what you call it, however, the Aurland loafer – inspired by moccasins worn by Native Americans and shoes favored by Norwegian fishermen – is simply a penny loafer. It comes in many designs and colors and has the distinctive cutout that can house a penny, if not a dime. But a true Aurland loafer comes from the Aurland Shoe Factory.

Belgian Loafer

Like the Aurland, the Belgian loafer is characterized, in part, by locale: in this case, Belgium, thanks to the original design of shoemaker Henri Bendel. It soon became popular in the U.S., and has a few unique characteristics, including a small, easy-recognizable bow, soft-sole construction, and unique colors and materials.

Interestingly, only one retail outlet in the U.S. carries Belgian loafers (located in New York City), although they’re available to everyone online.

HorsebitLoafer

Think “Gucci” if you’re confused as to what qualifies as a horsebit loafer. Gucci, after all, capitalized on the popularity of the loafer in the 1950s and came out with its hand-sewn moccasin style with a “horsebit” – usually made of gold (the Gucci version), silver, or brass – included on the upper where the diamond cut would be in a penny loafer.

The horsebit is a dressier style of a loafer and indicates, in many cases, a certain level of class, or least a bit of preppiness. The Gucci horsebit costs several hundred dollars, so it may also reveal something about the wearer’s bank account.

How We Selected Our Best Men’s Loafers For 2019

A lot of men’s loafers look good but not all of them feel good or feature quality construction. In choosing the best loafers for our list, the shoe had to deliver in all categories, including comfort and durability.

The design and appearance certainly had some impact on our decision making, and we looked for loafers that are versatile enough for a variety of casual, semi-casual, and even formal settings. Last, but not least, we carefully considered the reviews of others, particularly the reviews of customers.


We’d love your input, too. Do you have a favorite brand or pair of loafers? If so, why? Have you worn any of the loafers on our list? We always welcome your feedback and suggestions.

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