The Converse Chuck Taylor High Street Mid makes the subject of our sneaker review section this week. Being around for over 100 years, the Chuck Taylor sneaker is undeniably one of the most iconic silhouettes on the market. The Converse brand has come a long way since its conception with many more styles that derive from its beginning concepts. The Converse Street Mid is one of these new versions of the classic sneaker that was released in 2018. Following Converse takeover by Nike in 2003 there has been a trend of modernizing the Chucks and equally important, make it more comfortable. The Street Mid was a result of this effort, being a mix of classic Chucks with an Aero Jam flair. 

How They Fit

We got our hands on a pair in navy, black and white that came out in 2022. Out of the box the shoes are lightweight and look like they were made to last. Like the classic Chucks, they run large so you want to go down at least 1/2 size smaller than what you normally wear. Overall they feel comfortable but it looks like they may require you to wear them a few times to get even better, especially in the rubber toe area where they get a bit narrow. Check out our Converse Chuck Taylor size chart if still in doubt about your size. 

Converse Street Hi Top Navy White 1

Converse Street Hi Top Navy White 2


The Converse Chuck Taylor All Star Street comes in all canvas as well as leather upper which makes them a good fit for any season. Compared to the classic Chucks these have the back sectioned from the rest of the shoe with a stylish sewing line. Combined with the midsection and the iconic rubber toe these rock a pretty stylish look. The mid silhouette is enhanced by a generous padding around the ankles which adds support for various activities on the “street” but even keeps your feet warmer during cold days. The tongue, which is kept in place by 2 side straps, features an equal amount of padding which adds comfort and versatility to the shoe. The ankle area has an elongation to the top where an extra pair of eyelets were added; you can either leave it unused and stick the tongue out for some street looks or secure it in place and get ready for some street balling. When we made this Converse Chuck Taylor Hi Street review we tried it in several instances and the shoe proved to be a versatile one with good performance in the gym, basketball, skateboarding and of course every day wear.

Sole Unit 

The sole unit is closer to the original Chucks as not much was changed. The removable insole made of EVA is the main source of cushioning for these sneakers. This makes them as comfortable as Chucks has always been when it comes to long hours of wearing them. It all depends on each one’s need for arch support, one department where this shoe does not do that well. If you’re planning on standing up for all day in these and you normally need some support these will not do it for you. The rubber midsole adds some more cushioning but again it’s limited. Along with the rubber toe and the diamond patterned outsole it does add a lot of durability to this shoe, one feature that Chucks are known for. It’s also worth noting that the Street sneaker runs a bit narrow especially in the toe area so if you have a wide foot you’re a bit out of luck, much like with the other retro sneakers. These  run true to size , however , if you are not sure what size to get you can check the Converse shoes size chart here

Converse Street Hi Top Navy White 3

Converse Street Hi Top Navy White 4

Bottom Line

To conclude our Converse Chuck Taylor Hi Street review, these are a nice twist to the classic sneaker by offering more comfort, especially in the upper area. This makes them a versatile shoe that makes them a viable choice for casual wear at school or on the streets, light gym, basketball and skateboarding. At the $60 price tag they are surely a sneaker worth trying. They are only available in men’s sizes and in various colors. Among high top sneakers for men these provide one of the best deals at this price tag. 

Update: In 2023 Converse released an updated version of this model, the Converse Malden Street sneaker.