11 Comfortable Mens Slip-Ons and Loafers

Men’s Loafers and slip-on shoes tend to be some of the most comfortable designs of shoes around, they come in all kinds of styles from casual to dress, so they can be worn with pretty much any type of clothing. The most popular styles include the latest comfort technology that will keep your feet feeling great, whether you are on your feet all day or are just out running errands. The main selling feature of a loafer is that it is easy to get on and off, which makes them a good option for travel or if you have difficulty bending over to tie laces. Slip-on styles of shoes can’t be beat for convenience, and they are also very stylish and on trend. The following are some of the most popular styles for comfortable currently on the market.

Rockport Men’s Style Leader 2 Bike Slip-On Loafer


One of the best all-around, top-selling loafers is the Rockport Men’s Style Leader 2 Bike Slip-On Loafer. This is a great style that can be dressed up or down, as it works really well as a work shoe whether your office is business casual or you need to wear a suit. Rockport are one of the best walking shoe brands due to their excellent shock absorbing rubber soles. The Leader 2 requires no breaking in period and will feel great on your feet as soon as you put them on. As long as you get the right size, they will hold up well when you are walking and not slip off. If they are a little snug when you first get them, you don’t need to worry too much as the leather will stretch out a little bit the more you wear them. The design is bike toed, so that means that there is a seam on each side extending forward towards the toe. Overall, it is a fairly stylish looking shoe, that is lightweight, flexible, easy to wear, and looks good in different types of situations.

Available from Amazon

Bostonian Men’s Mendon Dress Slip-On

The Bostonian Men’s Mendon Dress Slip-On is a comfy and inexpensive design that is great for those who are constantly on their feet or busy moving. These shoes are reportedly very durable and should hold up well to frequent wear as long as you spend a little bit of time keeping them clean and polishing them occasionally, as you would with any men’s dress shoe. The Mendon is a good option for formal and business casual wear as they are extremely lightweight, flexible, look clean and have no logos. They aren’t overly shiny or overly distressed, but rather they have the right amount of shine for a work shoe. The padding on the Mendon is very cushioned, so they are easy to wear for long periods of time. The only downside is that the grip is minimal and they can be slippery when facing wet or snow like conditions, despite having rubber soles. This is a great quality option for the price, that is versatile enough to work well with most men’s wardrobes.

Available from Amazon

Clarks Unstructured Men’s Un.Sheridan Slip-On

Clarks Unstructured Men’s Un.Sheridan Slip-On are a perfect example of the Clarks tradition of high quality, long-lasting shoes. This design is a best seller not only because of the great style, but they also are cushioned in a way that you feel like you are walking on air. Clarks usually don’t have much of a break in period and the soles are very light for a dress shoe. The Sheridan feature air vents, that can help if you have trouble with your feet overheating in leather shoes. This is another design that can be worn with business casual or more formal dress, and will work well for either situation. They are comfortable, they look great, and they are easy to get on and off for security when traveling.

If you love Clarks and are looking for a style that is slightly more casual than the Un.Sheridan, check out Clarks Men’s Escalade Step Slip-On Loafer.

ECCO Men’s New Jersey Slip-On Loafer


ECCO Men’s New Jersey Slip-On Loafer are one of Ecco’s most popular men’s dress shoes that are perfect for the office. Since they are ECCO, they’re extremely comfortable and incredibly lightweight. The soles a quiet, lightweight rubber that won’t make any noise when you are walking on hard floor, even if the soles are wet. ECCO shoes last forever and the New Jersey slip-on is no exception as it has the same great quality and good workmanship as other ECCO products.  Like the other styles listed above, this design goes just as well with jeans as with a suit, and everything in between. The New Jersey Loafer has almost no breaking in period and they will feel great right out of the box, they are comfortable with no inner seams to rub against your foot. The quality of leather is excellent, as it is thick premium grade leather. The rubber soles provide great traction even in rain and snow. The high quality interior lining and insole make the shoe very breathable and won’t cause your feet to sweat.

Available from Zappos

Dockers Men’s Agent Slip-On Loafer

Dockers are usually a pretty good brand for all things business casual, no it isn’t surprising that they have some decent slip-on styles that are great for the office. Dockers Men’s Agent Slip-On Loafer are an inexpensive option that offer a good level of comfort. Since these are a budget option, they may not last as long or wear as well as some of the more expensive brands. They are still a good style to consider if you are looking for something that is comfortable, looks modern and is appropriate for the office. If you clean and condition the leather, you can make the shoe last longer especially if it is getting exposed to inclement weather.

Available from Dockers

Sperry Men’s Hampden Venetian Driver



The Sperry Men’s Hampden Venetian Driver is the most casual looking shoe on our list. This style has a feel that is fairly similar to a slipper, but you can easily wear them to the office or out and about. These are a bit too casual to be worn with a suit, but they are great with jeans and khakis. This style has a lot of cushioning for comfort, but they don’t have much in the way of arch support. The soles are very flexible and lightweight. If you don’t like to wear socks with your shoes, Hampden may be a good option for you, as they are comfy enough to be worn with or without socks. Sperry’s are known for their high quality, traction of the sole, and they will usually last for years.

Available from Macy’s

Cole Haan ‘Tucker Venetian’ Loafer

Cole Haan ‘Tucker Venetian’ Loafer are just one of the many loafers that Cole Haan offer.  If you love penny loafers, Cole Haan is also a great brand to look through. The Tucker Venetian is a good style if you want a shoe that is high quality, but also super comfy. Part of the reason for the comfort of this shoe is that it has a good padded insole and flexible rubber sole. It comes in your basic brown and black, which are fine for most workplaces. The leather is high quality, and the shoe itself is very well made and durable. You can slide them on and off really easily and they fit well on most men’s feet. In the picture they look a little casual, but when they are being worn they are fine for most offices. The sole has great traction, so you can wear them in inclement weather without worrying about slipping. This is another popular choice for travel due to the versatility of the style and the comfort and the fact that they are so easy to wear. Cole Haan have also introduced a new, more expensive loafer called the Men’s GrandEvølution Venetian Loafer, that uses the same kind of Signature Grand.OS cushioning technology that is used in the super popular Zerogrand Oxfords that everyone loves.

Available from ColeHaan.com

Samuel Hubbard ‘Frequent Traveler’ Slip-On

The Samuel Hubbard ‘Frequent Traveler’ Slip-On are a fantastic shoe if you are looking to get a style that is a little bit more unique and fashionable. As you can probably tell from the name, this style is built for traveling. It is designed in California and then handcrafted in Portugal using full-grain cowhide leathers. The Samuel Hubbard brand claims to make the world’s most comfortable shoe and they could very well be right. This style has triple-density memory foam insoles that will conform to the shape of your foot. The insoles are removable if you need to add orthotics. The sole of the Frequent Traveler can be replaced through the companies Resole Program if it wears down.The founder of Samuel Hubbard started the Rockport Shoe company with his father in 1973, so this family has a long history in the shoe making business.

Reviews say the Frequent Traveler is comfortable right away upon first wearing. In person they are very stylish and sleek with a bit of shine to them. Most men seem to find them comfortable, with a great fit and easy to get on and off.

Available from Nordstrom

Mephisto Edlef’ Slip-On

Mephisto are known as a brand that makes very comfortable shoes and Edlef’ Slip-On is a perfect example of this. They will fit most men well, are comfortable beyond belief and are very stylish. They are long, streamlined design that can be dressed up or down. In person they look well made and high quality. Mephisto use something called Soft-Air technology so they are guaranteed to be super-soft and comfortable, even if you are walking long distances. Mephisto shoes can be somewhat pricey, but they have a reputation for being long-lasting and there is little to no break in period with this style. The key features of this shoe are the high quality leather that will mold to your feet, the style that works for both casual and dress situations, and the comfort level.

Available from Nordstrom

Skechers Men’s Segment The Search Slip-On Loafer



Skechers Men’s Segment The Search Slip-On Loafer are an affordable, office appropriate slip-on that are a little more casual than some of the other options on this list. They are made with an oiled Mohawk leather upper, and it has prominent stitching accents that adds a little bit of nice detailing. It also has a Relaxed Fit® design, so this isn’t intended as a snug fit. It is quite a big shoe with a very rugged shock absorbing sole. The insole is the standard Memory Foam Cushioned comfort insole that Sketchers are known for, and the tread on the bottom is very good for gripping the ground, even the tough weather conditions. They can definitely be worn as business casual, but perhaps not a great style if you are looking for a design for more formal wear.

Available from Amazon

 Hush Puppies Men’s Slip-On Loafer


Hush Puppies have so many good options for slip-on styles that I had a hard time choosing just one. The Rainmaker(pictured) and the Leverage are both good designs if you are looking for a versatile business casual look that could also work with a suit. If you want a more everyday, less formal look they have a lot of other options to choose from. Hush Puppies are known for the everyday comfort of the brand, so they are well worth a look if you need functional shoes that look and feel good for all day wear. They use a bunch of different types of technologies to help improve the comfort of their shoes, you can find out more about that here.

Shop loafers and slip-ons at HushPuppies.com

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