The Complete Men’s Guide | How to Look Stylish in StreetWear

The whole world seems to love streetwear. It’s comfortable, effortlessly cool, and will inject edge into every outfit you put together.

Streetwear is incredibly easy and straightforward to wear, but it is less easy to make it look both smart and stylish. Wondering how you can interpret streetwear into your smart-casual wardrobe, or even use it to inject an urban edge to your office wear? We show you how:


What is Streetwear?

Unsure about what streetwear actually is? Here’s a quick lowdown about the style, and why it seems to be dominating the fashion industry right now.

Streetwear is a style of street fashion that has an urban feel at its heart. The streetwear concept is rooted in Californian surf and skate culture, where it originated. Since then, the streetwear aesthetic has been adopted by the hip hop subculture, and has a youthful and urban feel.

The Complete Men's Guide | How to Look Stylish in StreetWear : Fashion | https://www.royalfashionist.comTraditional streetwear is loose and baggy, incorporating elements such as oversized hooded tops and graphic tees. In terms of accessories, baseball caps and sneakers are also an important part of the trend.

For many, the sneakers that you choose are considered the most important aspect of getting this trend right. They should be chunky, leather, and have a retro or vintage feel. White soles are essential, whilst the body of the shoe can be almost any colour of the rainbow; the only real limit is your imagination.

When asked how he would define streetwear, one of the most famous purveyors of the streetwear concept, Tommy Hilfiger, replied that “The aesthetic has to be a bit sporty, a bit athletic…It’s skate and hip-hop, but it’s not exclusively any one of these things.”

The Complete Men's Guide | How to Look Stylish in StreetWear : Fashion |

So how can you take all of these traditional streetwear elements and incorporate them to your current wardrobe? You’ll probably be surprised by just how easy it is! When you add streetwear to traditional and more formal looks, the two contradictory styles will compliment each other.

Experiment with Proportion 

Given that the traditional streetwear look involves wearing big baggy clothes, incorporating elements of this oversized style into your outfit will immediately give it a street style feel.

The Complete Men's Guide | How to Look Stylish in StreetWear : Fashion | https://www.royalfashionist.comTo keep things smart only choose one piece to be oversized, whilst keeping everything else close-fitting. Pair an oversized hooded top with a skinny jean or slim fit pair of chinos, for example. Or if you are looking for something suitable for a smart casual day in the office wear a close fitting suit with a slightly looser and more oversized shirt: wear this open without a tie to achieve a slouchy and casual feel.

The Complete Men's Guide | How to Look Stylish in StreetWear : Fashion | https://www.royalfashionist.comExperiment with different proportions until you find the style best suited to you, and your body type: some men look better in baggy tops with skinny pants, whilst others prefer a wide-legged skater style jean paired with a more closely fitted shirt or sweater.

The Complete Men's Guide | How to Look Stylish in StreetWear : Fashion |

The Complete Men's Guide | How to Look Stylish in StreetWear : Fashion | Axe Necklace

One of the most important aspects of streetwear is choosing the pieces you love and using your clothes to express your individuality.

This gives you incredible freedom to really think about what suits you, and what pieces you feel happy putting on each morning. As long as you think about both these elements when choosing an outfit, you’re sure to find something that suits you perfectly.

Add a Formal Coat or Jacket

One of the quickest and easiest way to inject a smart edge into any outfit is to add a formal blazer or jacket with a button fastening and slim lapels. This will immediately create a structured tailored feel reminiscent of suiting, and therefore give your overall look a more formal feel.

Now is the perfect time of year to experiment with this look, as it is quickly becoming impossible to leave the house without a warm overcoat thrown over every outfit! Use yours to cover hooded tops, graphic tees, and even a brushed cotton lumberjack shirt tied around your waist.

These iconic elements will immediately set your outfit apart and lend it a streetstyle appeal, without alienating you from the more formal, smart-casual crowd.

The Complete Men's Guide | How to Look Stylish in StreetWear : Fashion |

The Crombie coat, as demonstrated so stylishly above, is a great choice. It fits closely to the body which, combined with its long-line style, is incredibly flattering, but it is neutral enough to perfectly compliment more modern and fashion-forward streetwear pieces.

If you’re yet to purchase your new season coat then there’s no time to loose! The sooner you hit the shops the more choice of styles, designer and sizes you will have. Here are some of our favourite Crombie coats at a range of price points, ideal for recreating this look:

The Complete Men's Guide | How to Look Stylish in StreetWear : Fashion |

Choose Dark Colours

Traditional streetwear brands embrace all the colours of the wheel within their designs. However, if you want to look as formal as possible whilst still wearing your favourite streetwear pieces then look for dark colours.

The Complete Men's Guide | How to Look Stylish in StreetWear : Fashion |

The Complete Men's Guide | How to Look Stylish in StreetWear : Fashion |

Dark pieces have an immediately formal feel: it’s the reason that most men choose to wear a black or grey suit to the office. Whilst colour is fun and expresses your personality, an absence of colour shows that you are serious about what you do and helps to detract attention away from your outfit.

If you can’t wear black from head to toe then choose one iconic and statement-making black piece (such as a tee or jacket) and then add black accessories. These pieces will compliment each other and give an overall sense of the colour to your outfit.

Wearing black shouldn’t be confused with looking boring. One of the main reasons why the fashion pack wear black so often is because it allows the all-important details of your outfit to really shine through.

Why not make the decision to go back to black and let the structure, style, and proportion of your outfit really shine through and help you stand out in the crowd.

The Complete Men's Guide | How to Look Stylish in StreetWear : Fashion |

Love to Layer

Layering is a huge part of wearing streetwear, and you don’t have to let this element of the trend go just because you’re trying to smarten up! As long as you choose the right pieces, it is very easy to incorporate layering into a formal look.

The Complete Men's Guide | How to Look Stylish in StreetWear : Fashion | https://www.royalfashionist.comTry wearing a striped button down shirt open over a plain white tee. Alternatively, inverse this by wearing a patterned tee with a plain shirt. Top this with a bomber jacket or, for a more formal feel, a blazer and you will immediately be layering three separate pieces together like a pro.

The right streetwear look is all about choosing the best brand: the pieces that will earn you the most respect within urban circles are those from underground and subversive brands that reject the mainstream. A great example of this is Supreme, who create iconic logo tees with oversized prints and vibrant colour flashes.

Other great streetwear brands to look out for include Japanese manufacturer Bape, who have collaborated with big brands from Converse to Pepsi.

If you want something a little more out of left field then look to Huf. Huf started life as a skatewear brand in 2002 before entering the mainsteam: now their tees are worn by celebrities, and they have a host of A-list endorsements.

Sometimes though, branding just doesn’t matter. If you can find a fitted black hooded top without any branding or logos on it then buy it immediately and never let it go: this is the golden chalice of the smart streetwear look, because it is both neutral and a statement piece simultaneously, and it can be worn with anything. It is ingredient number one in the recipe for effortless cool.

The Complete Men's Guide | How to Look Stylish in StreetWear : Fashion |


Looking stylish in streetwear is much easier than you might think; simply pair an iconic streetwear piece with the classics you already have in your wardrobe and watch as the two conflicting genres work together and compliment each other.

The key to perfecting this look is to pick just one stand out brand piece per outfit and let that do the talking, whilst the rest of your outfit remains minimalist.

The key to feeling comfortable in this look is to find a statement piece that you love, and that suits your personality. Letting your personality shine through is the best thing about choosing to be part of a subversive fashion movement such as streetwear.

Finally, make sure you choose the right shoes. It doesn’t matter whether you call them sneakers, kicks, or trainers, the fact is that the shoes you have on your feet will be an incredibly important part of getting this look right.

Keep abreast of the latest athletic shoe trends, choose a brand that has good standing, and leave your tired old sneakers at home. You’ll soon be looking like a streetwear pro!

Tor Brierley is a writer and editor from the UK whose love of writing about fashion has taken her all over the world. With a passion for tailoring, Tor often looks to menswear for inspiration, and believes that fashion should be accessible to everyone. Tor has three main obsessions: red lipstick, her kids, and finding the perfect leather jacket.

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