I. Sneakers In general, you should look for sneakers that are classic and simple. There’s always a risk of looking juvenile in sneakers, but you can minimize it by wearing the right ones. I recommend avoiding sneakers with more than two colors and anything that was made to play a specific sport (unless that sport was tennis in the 1950s). If you’re in high school, you’ve got a lot more leeway here.

• Canvas sneakers/plimsolls – Very simple footwear that’s more appropriate for spring/summer than fall/winter (although that depends on where you live, of course). Solid colors like white, navy, tan and gray are the most versatile. Vans, Chuck Taylors, Jack Purcells and Keds are the easiest to find, but less common brands like SeaVees, Spring Court, Superga, PF Flyers, Tretorn and Feiyue are worth hunting down if you want something more unique.
• Low-top athletic shoes – This is a tough category, because it’s easy to go wrong. If you stick to classic shoes in simple colors and avoid over-detailing and technical features, you’re on the right track. J.Crew carries some New Balance and Adidas options, but you also can’t go wrong with simple Nikes, New Balance 574s, Onitsuka Tigers, or Sambas. At the high end, Common Projects and MMM GATs 
  

  are fantastic, but if you know what those are, you don’t need this guide.

• High-tops – Out of all the sneaker categories, these are the most likely to look juvenile, so I’d say avoid unless you’re already sure they fit your style. Nike Blazers 
  

  and Supra mid-tops 

  
  
  

  in solid colors are the most versatile choices (high-top Chucks too, but that’s really a different style than most people associate with high-tops.) I’m also a fan of the mid-top hikers that New Balance has been doing the last couple years (J.Crew pairs here, classic gray 

  

  ). There’s an entire sneakerhead culture built around Dunks, Raf and RO, and this intro guide isn’t meant for any of that. Check out Kicksonfire, slamxhype, hypebeast, or the SF Official Baller Sneaker Thread for more on that style.

• Avoid – Actual running shoes and Vibram Five-fingers toe-shoes – unless actually running! To preempt a backlash, no one is telling you not to wear athletic shoes for sports, but wearing shoes like this 
  

  with jeans or chinos is a style disaster. Be wary of fashion sneakers 

  

  from places like Diesel and Lacoste too – they’re often flashy and way overpriced for the quality. There are so many good, simple shoes that there’s no reason to pay for the fashion company markup. I’m sure someone will point out some reasonable ones, but they’re the exception. Unless you’re at the beach (or CA/FL), avoid sandals. Additionally – and I realize this is probably a controversial opinion – I’d avoid black sneakers completely, unless you already know that they fit your style. Black isn’t a versatile color, despite what most people think – it doesn’t match dark indigo denim, for example, which is what you’d probably be wearing with sneakers most often. Additionally, in menswear, black is associated with evening and formal events, which makes it a poor match for sneakers.