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Street fashion decoded: A breakdown of the styles you need to know

Clock out for the height of street fashion

Man walking up stairs wearing jeans and white sneakers outside concrete
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We spend a lot of time on the subject of how to dress — wearing the best suits and getting them to fit the right way, making a great first impression by having the highest-quality garments and the best grooming products. But one thing we don’t always talk about is taking who you are inside and letting it shine through. Sure, almost every piece of style advice we give here carries with it an element of personal messaging. But there is one way that you can do that without having to overthink it. You can embrace street fashion.

Sneakerheads. Surfers. Skaters. Ballers. There are so many versions of street fashion, or streetwear, depending on how you want to refer to it, that it can get hard to keep them straight. But the crux is that this is defined as anything worn by people in a casual setting, usually representing a subculture they belong to, be it punk rock, hip-hop, skaters and surfers, or athletics. Typically, those who embrace this clothing category are younger (in their 20s) and live in urban areas more than rural ones. But now that social media has taken off, these looks and these subcultures are reaching every corner of the globe.

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If you don’t know what streetwear is or if it is right for your aesthetic, we will break it down the best we can.

The differences between street and high fashion

Jacket shopping
Antoni Shkraba / Pexels

First things first, let’s talk about the difference between the two extremes of the fashion industry. While street fashion is on one side of the spectrum, high fashion is on the other. You will see a lot of the same people and brands try their hands at both, but there are some key differences between the two that you should be aware of:

  • The origins of high fashion are almost always in the big fashion houses you see on the runway. Names like Gucci, Armani, Versace, and Tom Ford are mainstays in the fashion weeks in New York, Paris, and Milan. Streetwear sees an origin in the everyday wear on urban streets. Influences from sports, music, and movies play a much bigger role in streetwear than high fashion.
  • The accessibility of streetwear is much more varied. While high fashion is known mostly for its exclusivity and being developed for the more affluent of our society, streetwear is seen as something for every person. From shoes and jeans to hoodies and hats, this is what the everyday man wears.
  • The focus of the two ends of the spectrum is also different. While the high fashion side of the industry tends to lean hard into craftsmanship, luxury, and timeless staples you can wear for years to come, street fashion is much more ingrained in comfort, practicality, and the message of the day.

The four types of street fashion

Man on couch in black pants and shoes
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Just like workwear has sub-categories focused on weather, industry, and function, street fashion has four different types that comprise the broad structure of their spectrum. Of course, there are always outliers, but these are the four significant sub-categories within the streetwear world:

  • Original – These are offerings from the brands that started it all, like Supreme, Hurly, and FUBU. While streetwear is now a $300+ billion industry today, these offerings came in on the ground floor and have deep ties to music, culture, and sport. These are not always the most popular brands anymore, but they are the most iconic and are the finds of the decade in the thrift store.
  • Sportswear – Now you are looking at the offerings that took those items made for the field, court, or gym and were adapted to live in the street. Jerseys, shorts, joggers, and sneakers that have the aesthetic and function of gym or sportswear but were designed to elevate your everyday outfit.
  • Adopted – Now we get to the result of anything doing really well; the rest of the industry jumps on board and gives it a shot. Brands will develop their own streetwear collections to grab a piece of that enormous pie, and these pieces are from those fashion houses that didn’t start with street fashion but adopted the category.
  • Luxury – Finally, no category in men’s style is complete without luxury options. This is where you will find the kind of streetwear the ultra-rich will elect. While you may see the guy on the street wearing the same outfit as his favorite musician, athlete, or actor, the brand it comes from will likely be different. This is the closest you will get to bridging the gap between streetwear and high fashion since accessibility starts to slip away.

How to implement it in your style

Man in all black walking
Samuel Lopes / Unsplash

Finally, we can talk about how to implement streetwear into your wardrobe and let it speak for you. Plainly speaking, this is the freest of free your wardrobe can get. While we will never tell you to wear sweatpants in public (those are loungewear and gym wear meant for the house or the iron paradise), you can mostly go all out with this look to let your personality show through. If you are always dressed to the nines and have difficulty dressing down, start slowly — one thing at a time. Swap out your sport coat or overcoat with a denim jacket. Swap your chelsea boots with elevated sneakers. Look at your favorite characters or figures in your entertainment and see what they wear. Take inspiration from them to recreate their looks in your own way. Remember, emulate, don’t imitate. Jack Reacher wears a t-shirt and jeans, but you’re likely not going to fill them out the way he does, so do the t-shirt and jeans your way.

Mark McKee
Mark is a full-time freelance writer and men's coach. He spent time as a style consultant and bespoke suit salesman before…
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