Men, it’s time to get serious about your style. If you pay attention to the word classic, it’s attached to simple styles, timeless looks, and evergreen wear that will only get better as time marches on. We’ve selected the very best classic sneakers for men, coming from both sides of the price scale, to help you outfit your walk-in like a true gentleman.
Your entire outfit starts from the ground up, just like anything else. Classic sneakers let you blend, twist and meld your fashions together, all tied up by your kicks. Simple styles, classic zeal, and the aesthetics that will make you look (and feel) like a million bucks.
The Best Classic Sneakers For Men
Vans Sk8 High-Top Classic Sneakers
You just don’t get more classic than Vans. We’re still mourning Warped Tour, but you can still feel like you’re part of the action with these classic streetwear sneakers. Slip into these high-tops and feel every layer of stitching wrap around your feet, keeping the shoe’s original shape, while proving to be supportive. Those stitches work all along the full canvas exterior to paint a fantastic image, working in sync with the white side stripe and pure white fabric laces.
When you get into the fine details, you’ll be walking on air with the durable rubber insole, perfectly cradling your feet as you walk. It isn’t enough to have a one-layer level of support, however; you also get Vans famous waffle bottom shoe design, aiding in absorbing impact and preventing fatigue. Just be sure to spot clean these Vans shoes and not immerse them completely in water, and you’ll be rocking this classic style for many years to come.
Reinforced stitching maintains shape throughout use
Available in over forty different color options
Full canvas outer
Durable rubber insole
Vans classic waffle bottom and textured outsole
- Weight2.87 pounds
Adidas Original Superstar Classic Sneakers
It’s almost impossible to look fresher than when you’re wearing a pair of Adidas shoes. Their original Superstar sneakers do more than just make you look excellent, they also cradle your feet in a soft interior for maximum comfort. Encased in the full grain leather outer, you get a durable rubber insole, adding another layer of support as you walk. You’ll find comfortable padding along the collar, as well as the inside of the tongue.
From there, you’ll note the classic triple stripe Adidas design, rolling down towards their standard textured outsole. If you flip these upside-down and take a look at where it all leads, you’ll see a weave pattern creating top-notch traction from top to bottom. The icing on the cake is the gold-colored Adidas logo on the outside of the tongue, adding a memorial touch of swagger to commemorate the original Adidas look that sparked a chapter in male style history.
Full leather outer
Comfortable and supportive rubber insole
Soft padding around the collar and tongue
Classic Adidas triple stripe exterior design
Weave pattern bottoms for excellent traction
- Weight12 ounces
Vans Slip-on Core Classic Sneakers
Vans are notorious for their low-tops and high-tops having a similar style to Converse shoes, but their slip-ons are a different story. Crafted from their design and a desire to make a better slip-on shoe, they built this full canvas model with a clean, linear look. You get two nylon stretch strips along each side of the tongue, letting you jump into these without having to pull your thumb against the heel.
No matter which of the fifteen unique styles you choose, you’re getting the same excellent support. Through the textured outsole and waffle bottom, you get superior traction and an excellent sense of stability. That point is driven home when you rest your heels on the footbed, and your ankles resting against the padded collar and tongue. Slip-ons are all about comfort, but durability shouldn’t be overlooked either. That’s why Vans ensured that these followed their standard for vulcanized construction, giving you more years out of every single pair.
Full canvas build
Classic textured outsole w/ waffle bottom design
Supportive and removable rubber insole
Vulcanized construction provides added durability
Padded collar and footbed
- Weight3 pounds
Nike Air Jordans Classic Sneakers
Everyone wanted a pair of Jordans. The iconic look that Nike helped develop is still as stylish today as it was back then, proving their ability to make a truly classic look. You start with the rubber and leather exterior, folding over one another to create this layered and glorious exterior. That trickles down to the rubber outsole, and the unique bottom with pressure-specific traction padding. Everything about Air Jordans are engineered for high performance, whether it’s basketball or parkour.
The magic of these Nike sneakers is inside. Once you get past the padded tongue and raised collar, providing stability and support for your ankles, you’ll find a breathable mesh interior. It’s not only completely removable, but the foam padding is as well, so you can keep your interior pristine after every single use. You get heel-to-toe shock absorption capabilities, helping you bounce back from every bit of stress you put on your feet. Jordans have remained a classic shoe for a reason; they perform, they appeal, and they hold nothing back.
Leather upper with primary rubber construction
Mesh lining is breathable for high performance sports
Textured rubber insole provides internal traction and support
Interior is removable for easy cleaning and care
Padded tongue and raised collar
- Weight2.65 pounds
Converse Unisex Chuck Taylor High-Tops Classic Sneakers
Converse has been one metric that classic men’s shoe style is defined by. Chuck Taylor’s work is always noticeable, especially when you take a peek down at the outsole. It’s constructed of high-density rubber, encapsulating the toe box area, and twisting into a split diamond bottom. These unique grips are pressure-activated, meaning they give you additional traction when you need it the most.
In the classic high-top design, you get an additional eyelet along the top, as well as a light strip of padding from the collar to the tongue. While it’s a bit tricky to get out, your insole is removable for cleaning, and provides a great deal of shock absorption. Every way you twist it, Chuck Taylor’s design is the epitome of a classic sneaker, an essential component to any wardrobe with a touch of streetwear. If you like one color sneakers, check out our guide to the best white sneakers.
Canvas exterior and upper
High-top design with extra eyelet
Rubber outsole and toe box
Durable rubber insole
Split diamond outsole for great traction
Converse All-Star Low Top Classic Sneakers
Converse isn’t going anywhere anytime soon, and neither is their All-Star low-top sneaker. Built on the basis of a style movement, the All-Star series it the most iconic streetwear sneaker that any man can own. You get over fifteen of their unique styles and colors to choose from, making this their most stylistically versatile pair yet. Slip into the padded collar, and sprawl your toes out across the synthetic insole. It is non-removable, but simple to clean when the time comes.
While the exterior and upper are made completely from canvas, your dual-layer outsole is created from a textured rubber. You get two different patterns, weaving together and into a blue stripe along the heel end of your outsole to add another dimension to your look. That outsole is vulcanized, ensuring a long lifespan, and maintaining shock absorption against whatever path you decide to walk on. Be sure to also check out our list of the best Asics shoes for more great items like this.
Available in over fifteen different designs
100% canvas construction
Textured rubber outsole w/ dual layers
Vulcanized construction provides added stability
- Weight12 ounces
Adidas Gazelle Classic Sneakers
Adidas shoes can be spotted from a mile away. Their Gazelle lineup marked one of their most versatile designs yet, available in over forty different colors and style options, so you can keep the shape and contour the look to blend in with your current wardrobe. Adidas crafted these out of 100% pigskin leather, which have been proven to withstand abrasions and warping better than standard calf leather that you find in most similar styled shoes.
The ankle dips down very low, but you’ll keep the padded heel cup to provide support. From the cushioned tongue to the footbed and insole, you’ll feel like you’re walking on air as the Gazelles encase your feet. Align these features with the non-marking outsole and synthetic lining, and there’s no path you can’t travel, no stone you can’t turn. For those detail-oriented gents out there, pay special attention to the classic Adidas triple stripe design, and gold-colored Gazelle above the top stripe. Our handy guide to the best skateboard shoes features more great products like this.
Over forty different styles to choose from
Crafted from 100% pigskin leather
Supportive rubber insole
- Weight3 pounds
Vans Unisex Old Skool Checkerboard Classic Sneakers
There’s no better way to relive the golden age of punk rock and skating. Even if it’s not a nostalgic look for you, it’s undeniably stylish. Checkerboard patterns have been one of those undying style choices since the 1950s, and the ways Vans weaves this pattern into their classic Old Skool unisex sneakers if fantastic. They went all-out with the collar, not just padding it, but actually cushioning it to allow you maximum comfort while staying supportive as can be.
Vans included their classic waffle bottom and textured outsole, resting beautifully beneath the canvas and suede upper section. One of the trademark features in these sneakers is the presence of anti-slip texture all along the insoles. If you were to actually use these to skate with, you’d need all the interior traction you could muster to maintain your footing. Love this shoes? Check out our review of the best Etnies shoes for our top picks.
Canvas and suede construction
Classic textured outsole w/ waffle bottom
Cushioned collar and tongue
- ModelU OLD SKOOL
- Weight3 pounds
Puma Smash V2 Classic Sneakers
You can’t deny the classic zeal that Puma brings to the table. Durable leather, synthetic materials, and a non-marking rubber outsole provide your feet with comfort and support from the minute you slip these on, until you kick them off at night. Puma includes a removable rubber insole to provide additional support, cradling your arch and building on the quality design of the bottom. Thanks to the diamond weave pattern, you’ll get near-perfect traction, which helps you keep your posture nice and straight.
Puma is famous for being true to size, meaning they have a very low percentage of returns based on improper sizing. When you’re ordering shoes online, that’s a blessing. Apart from the classic look, you also get even more support for your heel. From the padded collar and tongue to the extra strip of fabric in the back, comfort and support surround you at all times when wearing these Puma shoes.
Full leather and synthetic construction
Removable rubber insole
Additional fabric provides heel support
Diamond weave bottom provides fantastic traction
True to size fit
Reebok Royal Classic Sneakers
Last but not least, we have Reebok and their signature look from the Royal, their classic sneaker. While Reebok doesn’t allow it to reflect in the price, it feels like you’re slipping into a pair of luxury sneakers. Comfortable suede envelops your feet as you slip in, providing immediate warmth and comfort. That comfort is extended by the padded collar and tongue, aiding in your heel support. You’ll notice this Reebok shoe is a bit stiffer in the heel, and that’s due to a thicker build to ensure these will still look brand new in the years to come.
The support doesn’t end there. You’ll be wrapped in suede and nylon, but you’ll be walking on an EVA midsole. Between shock absorption and arch support, the EVA helps maintain your posture while walking, and reduces fatigue. Top it all off with the durable and removable rubber insole, and you’ve encased your feet in a sturdy pair of classic sneakers that are rated, on average, to last for four to six years. Now that’s getting your money’s worth.
Blend of suede leather and nylon
Forefoot flex grooves provide stabilization and top-notch traction
Supportive rubber insole
Padded tongue and collar
EVA midsole for enhanced shock resistance
- Weight4 pounds