5 Best Cool Shoes for Men: Your Buyer’s Guide (2018)


You’ve probably got at least one friend who wears a pair of what anybody would call “cool shoes for men.” The question we are here to answer is: when you gonna get yours?

When we talk about the what makes a shoe cool, we’re talking about a few things.

  • Quality
  • Reputation
  • Longevity

All the shoes on this list are top-quality pieces of work. As for reputation, you could sneak the word “popularity” in there, but that’s not what we mean. A shoe with a (good) reputation is bound to be popular, but popular things don’t always = reputation. By longevity, we mean a product — a shoe — that has stood the test of time. A shoe, or a brand, that’s been around awhile (because they make quality, popular stuff).

As you’ll see, the five shoes in the list are wildly different from each other. There are two sneakers. There are two boots. There’s an old school pair that’s become way new school lately.

Enough talk. Time to bring your cool up by getting down with a pair of these shoes. And p.s., if you have other ideas for cool shoes, hit me up. This list is a work in progress.

What are the Best Cool Shoes for Men?

1. Clarks Originals Men’s Weaver Moccasin – $101 and up (depending on size/color)

clarks mens weaver moccasin


I’ve got a soft spot for these KA, street smart shoes from the venerable Clarks Originals. If you want some cool new shoes, get on board with these.

The Clarks Originals Weaver is a beautiful shoe and it made a big splash earlier this year when streetwear giant Supreme collaborated with Clarks Originals on a great version of the Weavers. (That’s when I got mine.) This wasn’t the first time for a Supreme/Clarks collab. They previously worked together on Clarks Originals Wallabees. Unfortunately, you probably can’t get the collaboration pairs anywhere but after market sales, where they’ll set you back several hundred dollars. (Stadium Goods has one pair of Weavers, size 11.5, going for $350.)

You can get your hands — or feet — on the original Weavers, which feature all leather uppers with the famous Clarks Originals crepe sole. That’s the sole that was under the original Desert Boots, the iconic style that was created by Clarks Originals in the mid-20th Century.

I wore my Weavers a lot during a recent vacation in London (read: walking vacation), and they are super comfortable. (My other go-to pair on that vacation was the Chelseas lower in the list.) Besides the comfort, the pedigree and the look, there’s also the tiny detail of the fact that they’ve got just two eyelets so they’re very easy on, very easy off. Yes, that’s a small detail, but it’s cool.

We’re showing the Weavers in “peat suede” and they’re available in nine different colors (color options periodically change). They have an out-of-this-world customer rating average of 4.9 out of 5-stars.

For a company that got its start in 1825 in Somerset, England (where it’s still headquartered), Clarks Originals has definitely tapped into a very modern vibe.

Buy the Clarks Originals Men’s Weaver Moccasin here.

2. Air Jordan 1 Retro OG High Tops – $289 and up (depending on size)

air jordan 1 retro OG high tops


When you’re stepping into Air Jordan territory, you best bring a loaded wallet. When you step into a pair, you’re stepping into shoe history.

Jordans have been cited many times as the kickoff to the sneaker craze. It was a confluence of basketball legend Michael Jordan’s shoes, rap artists’ interest in them and sneakerheads’ worship of them that put the whole thing into motion back in the 80s.

The Air Jordan 1 is the original design in Chicago Bulls black and red. They’re often called the “banned Jordans” because the NBA said they didn’t meet the league’s uniform standards. It’s said that MJ was fined $5,000 every time he wore the shoes and that Nike happily paid the fine because of the publicity they gained.

These are the 2016 release of the Jordans. (They’ve been released many times over the years.) They’re an all leather upper with the Jordans logo on the ankle, the perforated toe box and, of course, the red Nike Swoosh.

You’ll note the price is high — as in above-the-rim high. The prices vary depending on size. By way of example, I wear size 13 and they check in at $449. Sigh.

While this list is about cool shoes for men, we realize that it’s not about cool shoes for rich men only. You can get Jordans in other styles and lower prices. The Nike Jordan 1 Flight 4 sneaks start at $70, as of this writing. (Note: It’s not always easy to find your size in the lower priced versions.)

Buy the Air Jordan 1’s here.

3. Timberland Men’s 6″ Premium Waterproof Boot – $63.17 and up (depending on size/color)

timberland mens 6 inch premium waterproof boots


In terms of popularity, this is a boot that hardly needs an introduction. Timberland 6″ boots were huge in the 90s and they’ve had a big resurgence over the past few years.

Like most every product that has a wide following, it’s the quality that leads the way. The Timbs are all leather with a padded collar. They’re waterproof and they feature 400 grams of Primaloft insulation for warmth and comfort.

Timberland was — and is — a brand that specializes in products for outdoor wear. Apparently DMX and other 90s rappers saw the stage as outdoorsy enough to require some great looking boots. That’s when the brand and the boots went en fuego.

But just because something is popular doesn’t mean you have to copy the style. That’s why it’s convenient that you can get Timberlands in as many as 42 (wha?!) different colors (color options change periodically).

Buy the Timberlands here.

4. Adidas Originals Men’s Stan Smith Shoes – $27.93 and up (depending on size/color)

adidas originals stan smith sneakers


The iconic Stan Smith shoes has been — and it’s safe to say, always will be — an…um…icon. Adidas made the shoe for tennis great Stan Smith back in 1973, when Stan (the tennis player) was ranked No. 1 in the world. His (the tennis player’s) endorsement of Stan Smiths (the shoes) is considered to be one of the top 15 most influential sneaker sponsorships in history.

Enough history.

The shoes are great looking. For a company known for its three stripes, it was a departure to not include three stripes on the Stan Smiths. Instead, the shoe was made with three lines of perforations (for venting) in place of three applied stripes. Since its first incarnation (if a shoe can be incarnate), Stan Smiths have been made in many different colorways.

We’re suggesting the original whites with the green heel tab and green logo (Stan, the guy’s, face) on the tongue. They’re full grain leather for the uppers and they feature Vulcanized rubber outsoles. The lace up closure is full, so you get a snug fit.

The shoes do come in other color combinations.

As an option, you might want to take a look at the Adidas Men’s Cloudfoam Advantage Clean Sneakers, which are very similar to the Stan Smiths, except with more perforations in place of the stripes.

P.S. I have two pairs of Stan Smiths. I had a third that I bought in the mid-2000s, and ended up using for yard work. I just was forced to give them up to ages. RIP, Stan Smiths (my shoes, not the tennis player).

Buy the Stan Smiths here.

5. Blundstone Chelsea Boots – $139 and up (depending on size)

blundstone eva rustic black chelsea boots


I have a pair of these Chelsea boots and I love them. Besides being great looking, they work fantastically. And by “work” I mean: they’re comfortable like you can’t believe. By “fantastically” I mean fantastic.

Any conversation about cool shoes for men has to include Chelseas. It’s a style that’s been around for a long time — invented in the mid-1800s by Queen Victoria’s cobbler…and, around the same time, by a company in Tasmania, Australia. Which brings me to what should become your next pair of cool new shoes.

Blundstone has a timeline about the evolution of its boots here. That’s why I’m giving credit to two different continents for the creation of the style. They’re called Chelsea boots because the hip crowd in 1960 England — in Chelsea — was wearing them all over the place. It was streetwear before streetwear was streetwear.

During my recent trip to London, these — along with a pair of Weavers, the first item in the list — were my go-to shoes for walking around the city. They were bloody brilliant.

These summer boots from Blundstone are the company’s lightest weight boots, with Blundstone’s Featherflex soles and a leather upper that features a reduced height through the ankle.

According to Blundstone, the new line of men’s summer boots “was designed for comfort and shock absorption, with added durability to the sole tread for improved wear and tear.” They’ve got two logoed pull tabs, one in front and one in back (the tabs are conveniently long, making the boots even easier to get on).

I learned of Chelseas when a representative for the company contacted me, suggesting I write about them as summer wear. It didn’t sound right — boots as summer wear — so she sent me a pair to try out. She was right, they are right and you’ll be all totally 100 percent right if you cop some. They go with just about everything, even shorts.

Buy the Blundstones here.

See Also:

Heavy, Inc. is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by linking to Amazon. Our product recommendations are guided solely by our editors. We have no relationship with manufacturers.
Would love your thoughts, please comment.x