10 of the Most Comfortable Men’s Flip Flops

The best men’s flip flops are those that look great, are durable, and are above all comfortable.  If you are the type of person who lives in flip flops all summer (or even all year long), we have come up with the definitive list of the best brands and styles on the market for men.

Read More: The Most Comfortable Women’s Flip-Flops with Arch Support

OluKai ‘Ohana Sandal

The OluKai ‘Ohana Sandals are a great option if you want a high quality, versatile sandal that has good arch support that looks great. The strap on the ‘Ohana is made of a water-resistant synthetic material, so they look like a slightly dressier shoe, but their functionality makes them great for the beach, since they can get wet or covered in sand without being ruined. The footbed is an anatomical ICEVA drop-in footbed with a compression-molded EVA midsole, so you know they are going to be super comfortable. They are a bit of an investment, but they will outlast many other brands, so you won’t have to spend as much money buying new footwear every year.

Available from Zappos 

Rainbow Sandals

Rainbow sandals have a pretty devoted following. They are kind of an interesting flip flop because they actually have a long and difficult break-in period that some wearers can’t get through. If you manage to break them in, Rainbow sandals will mold to your feet and are one of the most comfortable footwear that you can find. On the plus side, they do look great and will last for years. Rainbow has a lot of different flip flops to choose from, with their most popular styles having a nubuck leather y-strap, and a nylon toe piece. The leather styles are very versatile and will work well either dressed up or down.   If you need a good amount of arch support you can get their Double Layer Premier Leather with Arch Support , or if arch support isn’t too big of an issue, you can stick with their single layer options. Rainbows used to be made in the U.S, but most designs are now made overseas. If you are looking for made in the USA, try their line of made in America flip flops.  One other problem that you may find with some Rainbow designs is that they don’t have the best grip, so if you wear them when it is raining you need to be very careful.

They are a little pricey and aren’t a good option if you are planning on getting them wet, but they do look fantastic and are great in terms of comfort level (once they are broken in).

Check pricing on Amazon

Crocs Unisex MODI Sport Flip-Flop

If you need a comfy sandal that you can get wet, check out the Crocs Unisex MODI Sport Flip-Flop. They are great for the pool or waterside activities, since you don’t have to worry about fabric getting wet or ruined. The footbed is way softer than the standard Crocs Clog that most people are familiar with. The Modi also has a good amount of arch support, so you can wear them all day and they will still feel comfortable. They come in a lot of different colors, including some pretty bright options if that is your thing.

Available from Crocs and Zappos

Teva Men’s Mush II Flip-Flop

If you want a classic beach sandal you can’t go wrong with the Teva Mush II. This design is great for the pool, the beach, or just hanging around. The footbed is super soft and squishy and manages to mold to the shape of your feet pretty quickly without having to deal with a long break-in period. It comes with a nice looking fabric thong strap that has a few cool patterned color options. The outsole also has a little bit of grip, so they won’t slip as much as some of the other options if you are walking on wet floor. Overall the Mush II is good quality for a relatively low price.

Available from Amazon

Reef Men’s Rover Sandal

Reef flip flops are super popular and you can find their many styles all over the place pretty easily. You have probably heard of their Fanning design that has the bottle opener on the bottom of the outsole, which is cool and everything, but as far as comfort the better design to go for is the Rover. The Rover is great because not only does it have excellent arch support, but it is a great all-rounder sandal. It is water friendly, but doesn’t look too beachy, so you can wear it almost anywhere. It’s also very durable and has great traction so you don’t have to worry about slipping on wet surfaces. The Rover comes in multiple colors and requires very little break-in, since they have a contoured foam deck that makes them feel great almost right away.

Available from Reef and Amazon

Vionic Unisex Wave Toe Post Sandal

If you need some serious arch support you may want to look at the Vionic Unisex Wave Toe Post Sandal. This is more of an orthotic design than other options, they are a little expensive but that is usually the case with orthotic designs. Regardless, this is a super comfortable, supportive, and very durable shoe. The outsole is pretty solid and firm, which is helpful for support. If you want a flexible sole, this isn’t the option for you. Since it is a unisex style, you should be careful with sizing if you are ordering online. One really great features of the Wave is that it is easy to clean, since all you have to do is wipe them with a damp cloth and leave them to air dry.

Available from Amazon

KEEN Men’s Waimea H2 Sandal

As you may expect, the Keen’s flip flop offering is not your standard beach style, the Waimea definitely falls on the sporty side of things. They have that toe protection thing that Keen loves, which really changes the look from other brands. The Waimea has an EVA midsole, which provides a nice amount of cushion and helps to absorb shock. They are washable and water friendly, with a lightweight rubber outsole that has some traction, although it isn’t meant for hiking. This style is intended as a casual beach sandal not for hiking or anything like that.

Available from Keen and Zappos

Sanuk Men’s Fraid Not Flip-Flop

Sanuk make a lot of really comfy sandals, one of their best the Men’s Fraid Not Flip flop is particular favorite of many. It has a soft EVA footbed with suede lining, which is great for absorbing sweat and helping to stop your feet from slipping off the footbed. The strap is a frayed canvas that has a terry cloth liner that is notable for its worn in look. Sanuk’s are generally known for being pretty good quality, so you should be able to get a number of years out of this design.

Available from Amazon 

Chaco Men’s Flip Ecotread Flip-Flop Sandal

Chaco’s is another long-time favorite for a number of flip flop wearing men that I know. The Ecotread is one of their most popular styles, its popularity stems from it’s great design and the functionality of the shoe. The design is a little distinctive in person and may not be the best option if you are fashion conscious. The Ecotread’s are very durable overall (even the tread won’t wear out) and are actually designed to last a number of years. They have great arch support if you get the right fit, although they do require a bit of a break period so you may find them a bit uncomfortable at first. In case you were wondering about the name, they are called EcoTread because the outsole is made with 25% recycled rubber.

Find at Amazon

Sperry Top-Sider Men’s Baitfish Thong Sandal

If you like a classic style, look no further than the Sperry Top-Sider Baitfish Thong. You can find these sandals all over the place, they are particularly popular with sailors and people who enjoying boating because of nautical-inspired design and non-slip rubber footbed. For comfort they have a lightweight EVA midsole and the strap is full grain leather that is comfortable right from the start.

Find at Zappos

 

Flip Flop Fundamentals

Support– Support and comfort pretty much go hand in hand. If footwear has no support most people will find that their feet start to hurt fairly quickly. If you are young and have healthy feet, you can probably get away with wearing cheap drug store flip flops that have no support, but you may find that you pay for it later on with foot issues down the line. For most of us though, it is a good idea to have at least some level of support, especially if you are wearing sandals for long periods. Higher quality brands with good support are usually fine to wear all day long.

Style– There isn’t a lot of room to get super stylish when you are looking for a flip-flip, most are your basic y-strap, thong design. You can get sporty styles that will work well if you are super active in the summer like the Keen. If you want something that looks a little more upscale, you can try a leather strap design (i.e. Rainbow) or just a leather look-alike style (OluKai ‘Ohana). If you just want a nice design for the beach, you can’t go wrong with Teva or the Reef styles.

Material– Depending on when you are planning on wearing your footwear, it is worth considering what type of strap material will work best for you. Leather looks amazing, but you don’t want to get it wet, so it’s best to avoid leather strapped sandals if you are going to the beach. If you want a strap that will dry quickly you can’t beat rubber. The most comfortable straps are often those made of fabric, but in a summer shoe you will need to make sure the fabric is fast drying.

Versatility-If you wear flip flops all day, every day in the summer it is handy to have one that will not only  be comfortable wearing for long periods, but also adaptable to different situations or places that you may find yourself in. One of the most versatile styles that can get you through the summer from the beach to somewhere a little fancy is the OluKai ‘Ohana. They can take you from an unexpected hike to a more formal activity with no problem.

Break-in period– Trying to break-in some brands of flip flops can be an unpleasant experience. The brands to watch out for are Rainbow and Chaco’s,  as they tend to be notorious for long break-in periods. Unfortunately they are also two brands that are known for being the most comfortable once the break-in period is over and the sandal has molded to your foot.

Durability– If you are spending $50 on a flip flop most people are going to want to get multiple years use out of them. Of the brands we listed above, you should be able to get a minimum of 2 plus years out of most of the different options.

Water- In the summer you never quite know when you may find yourself around water, so it great to have footwear that you can get wet and it will dry off quickly and not be ruined. Some of the best styles for water use are Crocs, Keen, Reef and the Teva styles. You can get all of these styles wet and either towel dry them or leave them to dry in the sun and they will dry really quickly

Budget – To get a good quality, pain-free, non-slip sandal that you can wear all the time, expect to pay somewhere from $40-$70. Everyone obviously has different needs, but in this price range you have a lot of great options.

Fit– The fit of any style that you choose is going to be very important. When trying sandals on make sure the footbed is able to contain your entire foot, so you don’t get a lot of side-to-side movement. Your heel should be centered and aligned with the footbed. The toe bed should have enough room so your toes are able to spread naturally without hanging over the sides.

 

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