Here's what I wish for you; pick one of these styles and just go with it. Be the guy who rocks the all-stars or the blazers or the Sambas for 10 years.
If my wish doesn't match up with your desires, try them all.
I've owned almost every shoe on this list, so I can speak to overall comfort, style, and versatility of them all.
Converse All Stars
This shoe is the great equalizer. It is truly a pillar of style. It's so accessible. It is a beautiful thing. It pairs with anything and everything. Black, white, colors, whatever. High, low, it's all good. If you want to be an insanely stylish minimalist, you can just start right here.
Chucks are fertile ground for excellent collborations. One of my favorites from years past was the Converse John Varvatos with the crazy laces. (After writing this, I relized that they were indeed officially and serindipitiously 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 seamier seams.
Want to know more about the history of this glorious shoe? Check out this articel from Molly Isabella Smith on mrporter.com
The Blazer is for those who don't give a shit about the Ramones. Or for fans of The Iceman (no, not the pilot from Top Gun).
Or skaters from a certain era.
If you want the versatility of the Converse All-Star, but in a Nike, this is your shoe. The Blazer goes with everything, but best with your casual getup.
I love the big-arse 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. It's 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 a true classic.
No offense to anyone who fancies themselves prone to offense based on random sneaker rankings, I prefer this shoe to the Stan Smith, with its rubber toe.
The Samba are durable and well suited to pair with most casual wear. They actually 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 the bunch. Many of the Air Max interations have enjoyed a moment 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.
Also, let's be honest, one some of the Air Max iterations, the giant air bags are comfy but have always looked kind of overkillish. The 90 gives us a nice peek into that generation-defining tech without showing us the entire balloon— and even in the most bizzarre colorways, the shoe retains it's charm.
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 do recognize that these are one of the classics that people really gravitate towards, and very wearable as a general rule.
I do feel like these shoes go with anything, are affordable, and are great as a staple pair you can wear with anything.
Wear your Old Skool with pride, Vans folks.
New Balance 1400
New Balance makes super-versatile shoes, which to be honest were considered pretty frigging lame when I was a kid. But boy am I glad that turned around and New Balance found life as a streetwear stalwart, because they make shoes that go with anything are are probably the best in terms of atually supporting your feet, which is what shoes are supposed to do, right?
In my adult years I've had a few pair of New Balance, including those amazing Horween Artist Pack 998's that I somehow lost during a move. But my favorites where the Made in the USA J. Crew New Balance 1400s– if you can get ahold of a pair of those or something similar, I really do think those are some of the best sneakers you can buy, especially if you are a normal, non-hype-loving dad who wants to make sure his shoes support his good posture.
Update: Here's a link to a similar pair on SSENSE.)
The Jazz strike me as a unique shoe, inasmuch as they are similar in style to the New Balance shoes but don't carry as much of a reputation, either as streetwear or 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 stand out as a shoe with no pretentions and not a lot of baggage. They aren't fancy, they aren't going to be confused with the latest hyped-up-drop, 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.