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How to Dress: Streetwear

A guide.

By The Reflections OfPublished 2 years ago 5 min read
Top Story - June 2022
How to Dress: Streetwear
Photo by Joel Muniz on Unsplash


Starting from the bottom, we have trainers. But not just any kind of trainers. I feell like chunkier trainers look best. Most streetwear outfits have a baggier fit on the bottom half of the body, so having trainers with a bit of volume, a bit of shape ensures that it will be seen and not a mere memory in an pic for the 'gram.

My top choices are:

  • Nike Air Force 1.

The OG shoe for a reason. In a classic black and white palette, this staple shoe just works with so many outfits.

  • 2. New Balance 530 trainers.

Neon colours can be a daunting colour choice because of, well, how bright they are. So why not start with a pair of trainers that embrace it? I love the contrast of the tangerine orange with jet black. Launched in 1992 as a high performance trainer, this model is super popular for those who like to run and for those who don't.

  • Adidas Oswego

I love the oversized padded sole with the sock cushioning. Comfort is super integral to this culture within the fashion space, and I feel like this trainer ticks all the right boxes. This model has obvious 90's influence with the design, but this rich, woody brown offers ties into the collective love of muted colours.


Next up we have bottoms. If we thought the proportions with trainers were a little out there, this part of the outfit is where some people really like to play with their shapes. Here are some core pieces you can add to your wardrobe.

  • Cargo Pants.

This is definitely something seen in a lot of streetwear outfits across genders. Super comfy, they are great at giving a desired looseness to the bottom half, but still can be quite fitted around the waist or of the flip slide, a little bit roomier for a graphic t-shirt to be tucked in a little. I love the subtle details of this piece with the front and side pockets. Everyone knows that pockets make things, so, so much better.

  • Jeans.

Continuing on with the baggier approach, my top pick when it comes to jeans are a loose, wide leg fit. This style is great because it still defines the waist and butt, whilst remaining a roomier everywhere else. A faded black colour gives a vintage feel whilst a light blue denim wash is a classic option, too.

  • Sweatpants.

I couldn't forget sweatpants, now! It's a given that this fashion style has this piece in its repertoire. Sweatpants (usually) are the comfiest things that we can wear. Allowing freedom of movement, sometimes fleece-lined insides, and a waistband that gives us room, it's a great base for an outfit. I love how the black and white colour is divided between the legs. Super cool and quirky.

  • Skirts.

Skirts can also be incoportrated into this style too. For an updated look, think quilited materials with button details like this. Paired with a fly pair of trainers and a crop top and you'll have an outfit that looks edgy.

  • Shorts.

Nowadays it's rare to not see a pair of these in a streetwear picture. But...who can blame that because they really be doing great things for the ass. Just saying. A more casual pair like this always works!


This part of the outfit doesn't necessarily have to be oversized. You can really play with proportions here by wearing something more tight-fitting, or continue with the baggier fit. Your choice. Here are some things I like.

  • Graphic T-shirts

Love love the colour combination used here. The oversized t-shirt pairs nicely with the more tapered sweatpants whilst maintaining the black and white colour palette. Like the jeans I mentioned earlier, there is a sense of nostaliga inherent in Streetwear, so graphic tees, especially those with a slight fade, or even holes, really fit the vibe. Logos are a big theme for this way of dressing, so don't be afraid to rep a brand you love on your chest. I love this brand.

  • Crop tops.

Crop tops pair so nicely with the looser bottom because the contrasting fits look great together. There are some great styles out there like halterneck tops with thin straps, or satin scarf tops which show the back.


My most favourite piece of clothing in general is outerwear. Jackets. Coats. Gilets. I love them. I hate feeling cold and having something wrapped around my waist, or in my bag ensures that I hardly ever experience it. Anyways, you can see that outerwear designs in Streetwear really showcase the masculine influence, with patch pockets, zip details and padded materials.

  • Gilets.

Gilets are a great option for outerwear pieces, especially during transitional seasons. They can range from being light to more heavy-duty, and are an easy thing to throw over a jumper, or a t-shirt to finish off a look. The utility details paired with the bubblegum pink colour is a stylish combination, as elements of "hardness" and "softness" are juxtaposed.

  • Bomber Jackets.

Remembering how the origins of streetwear incorporated miliary elements, bomber jackets are the ultimate ode to it. Usually worn a couple sizes big, they look great with block colours on the front and colourful graphics on the back, or classic in traditional varsity colours.

  • Hoodies.

Streetwear is cosy, remember! Hoodies paired with jeans under a jacket is a total vibe. Brownie points if it's not yours because.........sharing is caring, right? A bright red hoodie looks great with an all black outfit, and a baby pink hoodie compliments earthy green cargo pants.


  • Bum bags

These have made such a comeback in the last few years and I'm here for it! They have a little bit more space than a purse, but less space than a backpack. Can be worn at the front, or at the back. I love the faux fur and checkerboard pattern of this one.

  • Bucket hats

I think bucket hats are really cool because of their slightly flared out shape. Accessories can really add that little something extra to an outfit, and hats are a great place to start! Bucket hats come in a variety of different colours and patterns so there is sure to be something that appeals to everyone. I love the colour combo of pink and orange on this one.

Thank you for reading, and I hope you gained some inspiration from this piece!


About the Creator

The Reflections Of

fashion! astrology! erotic romance! life! yeah!

💌: [email protected]

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Nice work

Very well written. Keep up the good work!

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Comments (3)

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  • Brandon M Harris2 years ago

    Excellent read! People think it's over analyzing, when it comes to fashion. However clothes set the standard on how you carry your self!

  • Carol Townend2 years ago

    I haven't worn streetwear for years. I loved this article because it's packed full of tips that are really cool. Maybe I'll be adding some new pieces to my wardrobe now, thanks!

  • Irene Mielke2 years ago

    I liked your description of fashion over the years!

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