Man Wearing Street Clothes

Men’s Street Style Guide

Street style is an undeniable force in fashion to be reckoned with, a sartorial language that just about everyone now speaks in some way, shape, or form.


Understanding Street Style

Man wearing All black Streetwear

Menswear has been steadily moving towards street culture as its popularity has increased, and for men looking to make a definitive style statement, it is a genre to be respected and embraced once and for all for its innovation.


What is Street Style?

Man sitting on a concreet ledge wearing a pink pullover hoodie and black jeans

Centered on individualism through personal sartorial personalization, street style made its presence known unapologetically in the 80s and 90s, eschewing the fashion trends of the moment and veering towards styles that had previously been relegated to the background. The trend featured a multitude of cultural references and intersectionalities of the mainstream, ultimately becoming an important part of concrete jungles everywhere that continues to this day.


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Where Did Street Style Come From?

Street style is just that – from the streets, direct to your door and in your face, a creative tour de force, an easily recognizable previous sliver of the fashion world that now stakes its claim as one of the most dominant forces within the industry. Men that appreciate street style and would like to further incorporate it into their wardrobe should first respect its long and storied journey into the mainstream with a brief overview that covers where it emanated from, how it has evolved, and the best ways to adapt to your personal aesthetic.


How Street Style Has Evolved

Man Wearing Street Clothes walking down a cobblestone road

Over the years, street style has transformed and reshaped the traditional menswear landscape, adding new layers and facets to fashion that have become generally accepted and incorporated by men en masse. One of the identifying characteristics of street style is how it rapidly changes with the times and pop culture, challenging true enthusiasts to stay up to date on the complexities and creativity behind the aesthetic.


Men’s Street Style: 2021

In 2021, men’s street style has evolved considerably to include many styles from other eras and genres that intersect, collide, and merge with seemingly no rhyme or reason, but ultimately to make for a stylish vibe. Street fashion in 2021 celebrates the grassroots perspective of the trend and is currently embracing its earlier iterations while combining the latest looks that can be seen on concrete jungles around the world.

One misconception regarding street style is that it involves oversized, sloppy clothing that ignores silhouettes. The truth is that street style encompasses layering and achieving the right fit for your specific body type as well as comfort level, the cornerstones to confidently pulling off the look. The rules are not as steadfast when it comes to street style, and the beauty of the look comes in creating a fresh, singular look that speaks to your individualism and sartorial spirit. Men’s street fashion takes a bit more insight and thought than other looks, but therein lies the beauty – men can take inventory of their shirts, pants, and shoe collection to create outfits that are stylish, comfortable, and ready for wherever the day – or night – takes you! Let's cover the basics of achieving the perfect look to match your personality.



The Shirt

Man wearing a printed button up shirt looking over his shoulder

Men that want to incorporate street style should be ready to go big and bold or stay off the concrete jungle. That translates to block colors, bold prints, and even shackets – the combination of shirts, hoodies, and jackets. Since street style also lends itself to less stringent rules compared to other trends, men have carte blanche to be more aggressive visually than usual, with inspired selections currently revisiting trends from the 80s and 90s, including neon and pastel colors. Cuban collared shirts are also big on the scene now, from the more fitted variety to the oversized if that is your preference.

Block colors, military camo, prints, and patchwork designs are back in fashion, and the more aggressive or unusual, the better. Take inspiration from the past and channel the Fresh Prince era with 90s neon and pastel chic – pared down with blue jeans and neutral separates. Cropped bomber jackets, parkas, oversized blazers, and shackets are another popular trend that men can layer with fitted jeans for a balanced streetwear look.


The Pants

Man wearing brown overcoat,  brown pants and

Street style has transitioned from its heydays of oversized, baggy jeans with multiple pockets to straight-leg and more form-fitting jeans that accentuate a man’s silhouette. Men should consider their choice of pants as the base or background of their overall street style look, which typically means – although not set in stone – pants that are more muted in tone or hue compared to your shirts or sneakers. The most important aspect here is comfort and how well your pants pair with your outfit.


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The Shoes

Floating sneakers

The shoes make the man is an adage that is pushed to the forefront in street style, with sneakers having the power to make or break a look. The approach to your kicks can run the gamut as there are a slew of brands and styles offered in shoewear for men, and this is where a man’s personal aesthetic will truly come into play. With the blurred lines that currently exist between streetwear and mainstream luxury fashion, sneakers can be as subdued or as blinged out as a man is confident to venture towards. Men that want to get more mileage from their shoes should opt for styles that are versatile enough to work with a variety of streetwear looks. Hi-tops, raised soles from Nike and Reebok are currently collections that are popular at the moment, but there are many others that produce distinct lines that can be worn with a broad range of street styles.


Man wearing camo pullover hoodie, black pants and white tennis shoes

Fashion inevitably changes and this mantra applies to men’s street styles as well. The beauty of wearing streetwear is that you have the ability to combine the best of many worlds to procure a look that showcases your singular style and personality. Men that adopt street style are directly inviting sartorial possibilities into their wardrobe that are meant to make a scene.

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