Classic men's sneakers are one of the most solid investments you can make. And these are the shoes that will always look good, no matter what. For extra style points, pick one of these styles and just go with it consistently. Be the guy who rocks the All-stars or the Blazers or the Sambas for 10 years straight.
I've owned almost every shoe on this list, so I can speak to the overall comfort and versatility of them all.
The Converse All-Star is the great equalizer. It is truly a pillar of style. It pairs with anything and everything. Black, white, colors, whatever. High-top, low-top, it's all good. If you want to be a no-fuss minimalist, you can just start right here.
Chucks are fertile ground for excellent collaborations. One of my favorites from years past was the Converse John Varvatos with the crazy laces, which lo and behold are actually called "Converse Crazy Laces."
These days, there are all kinds of variations of the shoe. If you want to branch out but not overdo it, may I recommend the Commes De Garcon Play version, and the 1970s Chuck Taylor with the more visible seams.
Want to know more about the history of this glorious shoe? Check out this article from Molly Isabella Smith on mrporter.com
If you want the versatility of the Converse All-Star, but in a Nike with the signature swoosh, this is your shoe. The Blazer goes with everything, but best with your casual getup.
I love the big swoosh on this shoe. Any color will do. And this is a great Unisex shoe, like many others on this list.
The Samba is a solid, no-nonsense shoe. Its cultural popularity ebbs and flows (according to GQ, the Samba is currently experiencing yet another "moment".) However, it's been around long enough to be called a true classic.
No offense to anyone who fancies themselves prone to take offense based on random sneaker rankings, but I prefer this shoe to the Stan Smith, with the bulky rubber toe.
The Sambas are durable and well suited to pair with most casual wear. They excel with shorts, without socks, and in a pinch, you can play some playground hoops in these things and not feel like your foot is going to explode.
Nike Air Max 1990
The Air Max 1990 is probably the most versatile of this bunch from a performance standpoint. Many of the Air Max iterations have enjoyed moments in the sun, but although the popularity of these shoes was retroactively built upon the success of the Air Max 95, retaining the classic Nike look (with the swoosh and all) puts these ahead of the pack.
Vans Old Skool
Although I don't have a ton of personal affinity for these shoes (didn't see them a ton growing up in New Egland and maybe I just don't have the nostalgia factor), I recognize that these are one of the classics that people love.
The Old Skool is a versatile staple that you can wear with anything. Wear yours with pride, Vans folks.
New Balance 1400
To be honest, New Balance was considered kind of lame when I was a kid. But that was a long time ago, and boy am I glad that New Balance found life as a streetwear giant because they make shoes that go with anything and are probably the best in terms of actually supporting your feet. Which is what shoes are supposed to do, right?
In general, these are some of the best sneakers you can buy, especially if you non-hype-loving dad who wants to make sure his shoes support his quest for good posture.
Similar in style to the New Balance, the Jazz doesn't carry as much baggage either as streetwear/dadwear.
Where these shoes excel: they are light and comfortable. While maybe not quite as versatile as some of the others shoes on this list, the Saucony stands out as a shoe with no pretensions. They aren't fancy, they are just solid and great as a sneaker, just doing sneaker things.
Like a good friend, a longtime lover, or free filtered water at Starbucks, I'm just plain glad to have the Saucony Jazz around.
What's your favorite classic sneaker? Let me know.