Originating on the streets of New York, California and Tokyo, street wear has been around for almost 50 years. It has made a jump from subcultures around skateboarding, hip-hop and surfing to the mainstream.

The major difference between streetwear and major fashion labels was that it was the people dictating what they wore. Instead of labels or magazines telling people what to wear, the choice came from those cultures.

In more recent years, many designers have made a name taking those looks as inspiration. Some of these emerged from counterculture such as:

• Stüssy
• Undercover
• BAPE

Now, it’s worn by icons, from those who grew up within these cultures to those adopting it. Some of the main proponents of streetwear include:

• Jay-Z
• Rihanna
• Snoop Dogg
• Zendaya

Here we explore the different kinds of street styles, and which one might work best for you.

Different street wear styles

Although there are many varieties of street styles, they can be grouped under these three categories:

1. Menswear for all

Items that were traditionally seen as masculine are huge on the streetwear scene. These include:

• Jeans – once they were workwear, now whether dark denim or acid wash skinny jeans, they’re worn on the streets. The 1980s are back.
• Bomber jackets – look to female stars such as Cardi B and you’ll see them rocking a bomber.
• Oversize clothing, particularly sweatshirts. No longer just the preserve of rap stars like Eminem, now girls get in on the act.

Who it might suit: Those new to streetwear, looking to break in gently. If you’ve traditionally dressed in clothes that are considered feminine, this could be a dramatic change.

How to wear it: Streetwear is about your own self-expression but these items should be comfortable.

Don’t be afraid to add some color. If your jeans are black, then choose a bold oversize sweatshirt. Maybe get a vintage bomber to pair with your jeans?

2. Comfort

Streetwear became such a big hit with people of every class and generation because it is easy to wear. In fact, a recent study showed that 57% people like streetwear because of its comfort.

A rule of thumb is that if you can’t skate in it, it’s not really street wear. First up – your feet need to be supported. Trainers are a huge part of street style. Trainers are the key to your outfit, you can make them the main focus too with brands such as:

• Nike Air Max ’97 – the most sought-after streetwear trainers
• Adidas Superstars – made popular by Run DMC in the 1980s
• Vans – the skate shoe since the 1960s

T-shirts and hoodies became popular streetwear because they are easy to pull on and go. Brands like Supreme have dozens of lines of these items because they are comfortable and stylish. Think of leisurewear such as joggers too.

Who it might suit: Those who have a relaxed attitude and don’t like trying too hard with clothing.
How to wear it: The best thing is that you can simply throw these on in seconds. You don’t have to worry about styling them.

3. Contemporary art

Graffiti has always been a part of street wear; in fact, you could call them bed mates. Some designers borrow from contemporary art while others are inspired by classic pop art. Luxe fabrics paired with contemporary art are definitely in. The newer designers including:

• Kith
• Gosha Rubchinskiy

Will appeal in this area.

Who it might suit: If you’re bold and brash and like to make a statement with your clothing, grab these styles.

How to wear it: Clash, represent and own what you’re wearing. This style is made to be seen.

Wearing clothes that make you feel good

Street wear seems here to stay, but that doesn’t mean that you must adhere firmly to the trend. The whole point of the style is to be comfortable in your own skin.

For some, that’s displaying their culture in everything they wear. For you, it might be a vintage pair of trainers.

Mix and match brands if you feel like it, go low-key for days when you’re chill. Remember your swagger is individual to you.