Modern Fashion 101: The Basics of Streetwear

Streetwear is one of those easily misconstrued fashion trends that people think it’s easy: just slap on any old pair of jeans, a tee, a hoodie, and some trainers, and you’re just a regular hype beast aren’t you?

Well, not quite.

Streetwear, both for men and women, is more than just the latest release from your favorite IG influencer; high-end street fashion requires melding complex designs with pop culture savvy, the latest trends in haute couture, and of course, self-awareness.

As with fashion in general, Streetwear is all about matching the right pieces and brand with one another, all of which require a lot of smart judgment calls. But aside from making informed decisions, great Streetwear relies on reaching into some staple outfits and pieces. If you can create a base of some Streetwear regulars, you can expand it further and create a wardrobe that is fashion forward and definitely better curated than some ‘luxury’ influencers out there.

The basics of Streetwear, however, are less about specific pieces and more about looking for certain characteristics, such as:

Fabrics: In Streetwear, cotton is number one. This means finding pieces that utilize classic cotton styles and textiles: chambray, jersey, twill, and oxford cloth are just a few choices to keep in mind. Decorative cotton fabrics, like seersucker, are great and all, but they’re more in the territory of classic mens wear than actual street fashion, which is something to keep in mind.

On Shape: There are 2 schools of thought regarding the shape of street fashion: the classic approach is to lean more on loose-fit: loose chinos, baggy shirts, beanies, basically classic 90’s RL. The modern approach, on the other hand, leans towards a melding of loose fits, like drop crotch pants (a go-to, if you ask me), with longline cuts. Either way is fine.

Consistency: You might be wondering why a hard definition of Streetwear is missing from this article; that’s because Streetwear, like most fashion trends, does have several definitions that might differ from brand to brand, country to country, subculture to subculture, and so on and so forth. What does remain consistent among all definitions is, well, consistency: pick a mix of styles, and stick with it.

Now that we have our street fashion mindset in the pocket, let’s take a look at some street fashion staples you should have in your closet.

Classic Dark Blue Jeans

The foundation of any good Streetwear is some good ol’ fashioned pair of jeans. And it makes sense; after all, pop culture appropriated jeans into the youth subculture a long time ago and has become synonymous with urban attire. Depending on which school of thought you adhere to, you can either go for something baggy or something selvedge. Either works, I think, but as long as it has the tell-tale strip going up the leg, then you’ll be fine. The reason for this is that this strip is an indication of quality: denim is sturdy because of that stitching, so don’t leave home without it.

Regardless of whether it’s American, European, or Asian Streetwear, one thing is clear: the only acceptable wash is raw denim. Yes, there’ll be a few outliers here and there, but raw denim is undeniably the Streetwear choice of wash. The idea, of course, is that the distress and fade of the denim is natural; your jeans have seen things, man, and you yourself have undergone adventures no other soul has gone on, seen things people wouldn’t believe. And if you haven’t, well, at least there’s a way to get your jeans to look like it did. Of course, you could just buy a pair of jeans and wear them out naturally, but who has the time for that?!

Army-Inspired Outer Pieces

Image from Unsplash

There’s just something about Army outerwear that just lends itself naturally to Streetwear, despite both trends being almost in contradiction to one another: maybe it’s the classic masculine vibe of a good flight jacket, or the versatility of its pieces, whether its fishtail parka or a classic pair of camo pants. Whatever the reason, it’s all about how it ‘fits’ within your whole ensemble.

Sweats for Days


Other than denim jeans, a pair of sweatpants, once considered the epitome of the slacker/slob but now the fashion-forwards staple piece, can elevate an outfit, if paired properly. As mentioned, sweats were considered lower-class affair; how different it is now, where the humble sweats can be considered the rich and famous’ status symbol.

“Statement” Tees

Screen-printing, or the practice of hand-printing t-shirts with customized designs, invaded all aspects of urban street culture sometime in the late 80’s/early 90’s. It allowed some progressive couture thinkers to really think outside of the box and creating a Streetwear staple that has persisted well into the modern era.

Classic designs, of course, are the best. Stick to minimalist designs, like white tees with a simple statement.


Image from Unsplash

Probably the most recognizable aspect of Streetwear, the hoodie entered the Streetwear subculture naturally; after all, what’s more ‘street’ than a hooded jacket?

Of course, not just any pair of hoodies will do: original fit pieces, that is, tight cuffs with a sizable hood and a short body, are classic. However, Japanese-made sweats are seeing a lot of wear as well: big sweats, big graphics, big statement.

Pumped-up Kicks

You could literally go with just a simple, well-fitting pair of jeans and a simple white tee and just pair it with a pair of classic kicks and you’d be Streetwear king. THAT’S how important the right pair of shoes are to Streetwear.

You know exactly which kicks I’m talking about: Jordans, Air Max 1, Sk8-Hi. Any of these are fine. In fact, you could just stick with a pair of two of these and you’d be solid.

But without getting into specifics, if you’re looking to get on the trend, the current flow seems to be leaning towards more about sports styles like basketball and tennis and less from the running trend. Just beware: the sneaker culture moves fast and leaves thousand-dollar pairs of shoes behind in an instant.

Build a solid Streetwear base with a pair of court trainers, a running model, and maybe some school bully trainers. Chunky is funky, and bold is brash, remember that.


As with any fashion trend, it’s all about finding the right base to work with so you can experiment to your heart’s content. Along the way, the best thing you can learn is sorting out the temporary from the classic, the trendy from the timeless.

It can get expensive, and sure, you might feel like you’re burning your hard-earned money from time to time, but the moment you build your trademark look, the whole process will feel so worth it, especially if it’s something you can wear every day and still get compliments every day.

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