In the realm of men’s fashion, one trend has been consistently held in the spotlight for the past couple of decades: streetwear. Defined by its bold and expressive aesthetics, streetwear has evolved from a niche subculture into a global phenomenon that continues to inspire and shape the way men dress in urban settings. 

The beauty of streetwear is that it is so versatile and pieces can be worn throughout the season, and once you invest in a few staples, your streetwear looks become immediately elevated and timeless. 

This guide explores the world of men’s streetwear, delving into its rich history, key style influences, and the latest trends that make it a beloved and dynamic part of contemporary fashion.

The Evolution of Streetwear

To understand the current state of men’s streetwear, you must first understand its roots. Streetwear, as we know it today, emerged in the 1980s and 1990s, largely shaped and mastered by the hip-hop and skateboarding scenes that brought this style to life. 

A lot of brands took inspiration from that and became pioneers for this movement by embracing the DIY spirit and adopting anti-establishment and countercultural ethos qualities. It truly resonated with multiple generations.

The hallmark of early streetwear was its emphasis on men’s graphic tees, baggy jeans, and bold, unique, attention-grabbing designs. Some of them were designed with their own logos to go on products and became an integral part of streetwear, serving as a means of self-expression and rebellion against mainstream fashion.

Over time, streetwear gained momentum, transcending into high-end fashion. You could say the rich do steal from the “poor,” or more accurately, the middle to lower class, in many ways and streetwear was one of them. Brands like Gucci and many others have dipped their toes into streetwear, creating the Avant Garde fusion and subgenre known as “luxury streetwear”.

Key Style Influences


Modern men’s streetwear has always drawn inspiration from various cultural, artistic, and subcultural influences. Where you can still find some original inspiration today, from the 90s to the early 2000s: 

Skateboarding Culture

Skateboarding has had an enduring impact on streetwear with their love for baggy pants, oversized tees, and functional sneakers, all thanks to the skateboarding scene.


The hip-hop music genre from the early 2000s to this day inspires men’s fashion choices and has played an integral role in shaping what we see as streetwear today, such as puffy coats and tracksuits. Iconic artists such as 50 Cent and Notorious B.I.G. were trailblazers, setting the stage for streetwear’s rise.

Japanese Street Style

Tokyo, in particular, has been a hotbed of streetwear innovations. Many premium and luxury brands have significantly contributed to the global reach of streetwear, and new innovations from this style are still being produced and loved.

Punk and Grunge

Elements of punk and grunge fashion, such as distressed and ripped clothes, band tees and combat boots, have been adopted by streetwear. It’s becoming more apparent that streetwear in modern settings is more of a collaboration of many other styles but on a minimal level.

DIY and Customisation

The ethos of DIY and self-expression remains a core element of streetwear. Customisation, including sewn patches, hand-painting, distressing and many more, allows wearers to create unique, one-of-a-kind pieces.

Trends in Men’s Streetwear

As streetwear continues to evolve, new trends and styles emerge each season with similarities to the past. Here are some recent trends in men’s streetwear that aren’t going anywhere:



A growing trend across this generation and around streetwear is minimalism. Clean lines, monochromatic colour schemes, and a simple brand are replacing the bold men’s graphic tees that were a staple of a real skateboarder.

Brands are taking inspiration from these eras and adapting them to a more rediscovered aesthetic to co-inside the ‘millennial grey’ and overall minimalism vibe a lot of people are on board with.

Utility Wear

Inspired by workwear and military clothing, utility wear has become increasingly popular with adaptations into cargo pants, vests, and tactical gear. They have now become staples in avid streetwear enthusiasts wardrobes.

 Vintage Revival

Vintage-inspired streetwear has officially surged. Nostalgic pieces from the 90s and early 2000s are being reimagined by modern brands and everyone is going crazy for them.

Gender-Fluid Fashion

Men’s streetwear is also becoming more inclusive, blurring the lines between male and female. Androgynous and gender-neutral styles are gaining prominence, reflecting the shifting cultural landscape.

Collaboration Culture

Streetwear is in full swing when it comes to collaborations. Brands often collaborate with artists, designers and other brands to create unique, limited-edition collections. These collaborations generate buzz and are highly sought-after by brand lovers and collectors.


Eco-conscious streetwear brands are on the rise, not to mention most people love original pieces from the 90s and early 2000s, so they are scouring vintage stalls, car boots and charity shops for them rather than buying the 2.0 modern versions, which saves clothes from reaching landfills but also supports charity.

Simple Ways To Incorporate Streetwear Into Your Style

If you’re looking for new ways to add some streetwear to your style, here are some tips for you:


Begin by adding some streetwear classics to your wardrobe, such as graphic tees, heavyweight hoodies and some versatile sneakers. These pieces can be mixed and matched, creating endless options while being extremely comfortable at the same time.


Essential for colder months is a fundamental technique in streetwear. Try combing your oversized tees under your hoodies and lightweight jackets to create a dynamic, warm and textured look.


Don’t sleep on the importance of accessorising; adding things such as a cap, beanie, rings and maybe some statement sunglasses can really elevate your look and bring it all together.


Footwear is a critical component of streetwear; high-top sneakers, adidas Gazelles, and classic vans are adding to streetwear history while still being extremely fashionable.


Customisation is a hallmark of streetwear; considering what unique designs to add to your clothes can be daunting but as long as it’s true to you and you have fun while creating your art, then you’re doing it right.

If you don’t fancy painting, try ironing on patches that you get from any retailer.


Men’s streetwear is more than just a fashion trend; it’s a culture that has evolved from its subculture origins to influence mainstream fashion. Its dynamic nature means that streetwear is continually changing, drawing inspiration from various influences and adapting to contemporary tastes.

Whether you’re an avid streetwear enthusiast or someone looking to dip their toes into this urban style, the key is to embrace comfort and self expression. From minimalist looks to vintage revivals, streetwear is a canvas upon which you can tell your own story.