Adidas Stan Smith
Hipsters, sneakerheads, and regular Joes alike have all welcomed back the almighty Stan Smith into their daily rotation with open arms since they were released back into the wild a few years back. The Stans embody minimalist design, going so far as to replace the iconic three stripes trademark with ventilation holes for the sweaty-footed people out there. The shoe market might be flooded right now with different variations of Stans, but the white/fairway green or white/navy models should always be your first choice. Boasting better leather some of the other kicks on this list, they also won't crush your wallet if you need to re-up after a rough weekend. For almost any casual occasion, the cornerstone of the adidas Originals line fits the bill. Roll up your pants legs to show off some sock style, or take advantage of what's left of the Summer to pair them with no show socks, chino shorts and a button up, polo, or popover.
Nike Air Force 1
This shoe was such a staple among hip hoppers worldwide that a pre-Real Husbands of Hollywood Nelly even dropped a hit song about them. They go by many names: Forces, Uptowns, AF1s, and so on, but they all serve the same purpose as the go-to retro basketball shoe respected by sneakerheads the world over. Air Force 1s are defined by their super chunky sole and no-nonsense design, and have been resurrected in recent years after a dip in relative inactivity. Thanks to deep roots in hip hop, to rock the Forces just right, your streetwear game should be razor sharp. Because of their relative bulkiness, it's best to wear the low tops with straight fit denim or chinos. Buyer beware, a tapered leg with low top sneakers can make your feet look like canoes, not to mention reveal yourself to be a man who doesn’t respect proportions. While that might be ideal in conveying to the ladies that you're packing a third leg, it's a sartorial no-no. The high tops on the other hand, are way more forgiving when it comes to a skinnier leg opening. Stacking on your pants/denim will naturally increase, but so long as the stacks aren't folding over, you're in good shape. The highs are also a little more adaptable to non-streetwear 'fits, so if you've got to choose between lows or highs, stick with highs.
The Minimal Sneaker
Thanks to high end brands like Common Projects, the clean, simple leather sneaker is has ascended to next-level classic status. Gaining most of it’s cred from the trickle down effect from the high-fashion runways and the growth of athleisure, everyone from sneakerheads to style noobs are rocking a simple white or black leather sneaker. Owing a lot of it’s value to its sheer versatility (it works with pretty much everything in your closet, including your suits on a night out), the minimal sneaker is now an absolute must-own. Thanks to it's popularity you can find them at many price points but the key is to make sure you keep it simple, the minimal vibe should be just that, minimal. A clean leather upper in white, black, or primary color, some high-quality leather, and an icy white sole are all you need.
Shoutout to Vans, the inventors of timeless, casual skateboard kicks. It was a struggle choosing between the Classic Slip-On and Authentic, but the latter wins based on the versatility. The presence of laces rather than elastic stays dresses up the Authentics just a tiny bit more and making them more acceptable to rock during various occasions. They're best as everyday wear and work with pretty much everything from shorts, to denim, to chinos. Seeing as these particular Vans have a very low profile, a more tapered leg is definitely the move. Take your authentics as casual as you like, t-shirts, flannels, and oxfords are easy matches with denim or chinos. And always cop the Authentics in twos, aside from limited releases, doubling up shouldn't run much more than a night out on the town and that way you’ll always have a fresh pair ready.
From it’s first incarnation as the first OG basketball kicks to the runways of fashion designers like John Varvatos, best believe they'll stand the test of time decades from now. A general style principle is leather Chucks can be dressed up and kept clean, whereas canvas chucks look a little better with some visible wear and tear. Everyone from punk rockers to gangsters wear them proudly, so chances are you fit somewhere in between that spectrum, so you're good to go. Finding a color you like is not a problem here, there's a little something for everyone. The timeless style makes for easy pairing with all your casual fits. If there’s a better match with denim and a t-shirt, we don’t know what it is. Even if they look good a little beat up, keep some shoe deodorizer in case you love wearing them a little too much, the grunge smell doesn't have to match the grunge look.