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Streetwear How-To Style Guide: Different Types of Oversized Shirts

Streetwear How-To Style Guide: Different Types of Oversized Shirts

Do you find that the oversized, baggy T-shirt trend is now on the rage? People are now wearing these loose fit tees on the streets, and they are quickly becoming a replacement for the regular fit shirts.

The origin of streetwear


Hiphop rapper in streetwear style. Image credit: The New York Times

Streetwear was a style inspired from the hiphop rappers and skaters in the past. For the ease of movement, they required more loose fit and comfortable clothing. Also, expression of oneself is very important to them, which led to the creative slogans and designs.

skateboarder street wear

Skateboarder in street wear style. Image credit: originboardhshop

Although street style used to be a minority fashion style, it has started to increase mass market appeal in the late 2010s.

supreme lv 2017

Supreme x LV collaboration in 2017 brought Supreme to a luxury brand status. Image credit: heuritech

The collaborations like global luxury brands like LV and streetwear brand Supreme helped bring street style into the spotlight too.

monclear collab

Monclear x Japanese streetwear Hiroshi Fujiwara collaboration

Street style now changed from a style for hobbyists, into a casual daily wear for everyone.

How is streetwear fashion style defined?

Street style comprises of oversized T-shirts, sweatshirts, hoodies. Usual accessories include simple ones like ballcaps, chain bracelets or necklaces. Streetwear people usually match the style with sneakers.

Nowadays, people are searching not only for style, but also comfort. They are slowly discovering the greatness of oversized fit.

Today, we will be introducing the different types of shirts the streetwear fans will love, and also how to wear them correctly.

1. Oversized T-shirts

ambler korea beam tshirt

First up, we have the oversized T-shirt. Think of fashion trends in the late 90s and early 2000s for inspiration. But if you’re buying an oversized tee for the first time, don’t get an XL and call it a day.

Nowadays, fashion brands make loose fit clothing in various sizes. You can certainly find a size that suit you best. That will provide a comfortable fit but gives some structure to your look.

Drop shoulder fit in oversized tees

ambler day tshirt

An important feature in oversized tees is their drop shoulder fit. Drop shoulder fit means that the T-shirt will drop off over the shoulders. Usually, the clothing shoulder width is longer than your shoulders.


But by allowing it to drop down at the shoulders, it gives a more casual look. This also extends the sleeves such that they almost reach your elbows. As oversized T-shirts have a longer shirt length, the longer sleeve helps to give the tee a more structured look.

Different style of oversized tees

We’ve divided oversized shirts into five design types, all of which are popular Korean styles:

Classic oversized tees

fila oversized tee

Firstly, there are the classic designs. These are usually the most popular collection of a brand. They also give a slight vintage vibe.

They give a causal-chic look and can be easily matched in outfits. They can also work with or without layers and accessories.

fila serif oversized tee

If you’re on the go, you can just pair them easily with a nice pair of jeans and sneakers.

champion basic tee

Since the T-shirt has the baggy look, make sure your jeans are well-fitted. Loose, ill-fitting jeans may make you look sloppy as opposed to relaxed and casual.

You can also add subtle jewelry like rings or necklaces to complete the street wear look.

Cool oversized tees

donut boy adlv

Oversized tees also allow for cool designs to be featured. ADLV is one of the fashion brands that incorporated an edgy vibe to their designs.

astronaut boy adlv

This make their T-shirts cute yet hipster cool at the same time.

Basic logo oversized tees

oioi blue tshirt

These are the basic range of any fashion brand. For example, Supreme is known for their iconic tee with the red Supreme logo at the front.

adlv basic tee

ADLV is also known for their basic short sleeve T-shirt range that showcase their logos on a plain color oversized T-shirt.

champion logo tee

Likewise, almost all street style brands also have the basic logo oversized tees in their collection.

nerdy hot pink shirt

Like the classic designs, they can be easily paired with any outfit. They also come in an assortment of colors to choose from.

Cute oversized tees

ambler wanted tshirt

Nowadays, many streetwear brands are incorporating cute designs into their T-shirts.

aqo tshirt blue

Brands like Ambler Korea and AQO Studiospace show you that cuteness can go well with streetwear style too.

ambler tshirt beam

These designs usually have the cute teddy bears or other cute animal details on them. The design speaks for itself, and there is no need for further accessories.

Creative oversized tees


moondial cpgn

Lastly, there are innovative oversized T-shirts. These brands transform a piece of clothing into a piece of artwork.

laundry line cpgn

Take the example from CPGN Studio. They incorporate many natural elements to showcase their thoughts about life.

whale flower cpgn

This relates to the wearers. Because clothing shouldn't just clothe us, they should also be a medium of expression of yourself.

2. Cropped tee

Cropped tees are also one of the much loved shirt style for the street style gals. Cropped tees are defined by being shorter in length and more body-hugging.

ambler cropped tee

They usually slightly below the chest and above the belly button.
The key is to get a cropped top that lands above your natural waistline.

fila cropped tee

To style a cropped tee, you can match it easily with skirt or jeans. You can also choose to layer up with long sleeve shirt or a cardigan over the cropped tee.

3. Regular fit T-shirt

Let's face the truth - oversized tees are raging now, but regular T-shirts won't be completely gone.

fila regular tee navy

These round neck Tshirts that provide a better straight fit have been the clothing choice for decades. This is also the usual style for European streetwear brands, as the Europeans prefer a more structured look.

guess regular fit tshirt

These T-shirts come in a variety of style, and are suitable both as home wear or for a casual day out.

For a comfy look, you can tuck into with a simple pair of jeans. To go for a semi casual look, you can wear it under a blazer or a vest.

Women can also wear a regular T-shirt with a pencil skirt. It gives a casual yet sophisticated look. Don’t forget to wear heels or some statement shoes to complete the look!

4. Long sleeve shirts

Semi casual shirts are a must-have in the wardrobe. These serve well on special days like anniversaries and special dinners.

checkered shirt rmtcrw

From button-downs to flannel, there are multiple kinds of long-sleeve shirts out there.

The checkered flannel shirt is one of the most classic design. It has a vintage style and goes well with any basic bottoms.

shoulder line shirt rmtcrw

These shirts can also be worn as an outerwear over T-shirts, making them very versatile.

5. Sweatshirts

ambler duty of love sweatshirt

Nothing screams casual streetwear style sweatshirts and hoodies. They are so easily worn, are so comfortable, and are perfect for a busy day of errands.

It’s okay to wear something oversized because sweatshirts are meant to be comfy. In fact, fitted sweatshirts are often unflattering.

aqo red sweatshirt

Other than that, always pair sweats with shoes or sneakers. Wearing boots, ballet flats, or heels will make you look out of place.

Sweatshirt outfits also make for a great couple attire too!

6. Hoodies

Lastly, we have hoodies, another staple of street Korean fashion.

spgn hoodie

Like sweatshirts, pullover hoodies are usually loose and oversized. As hoodies are usually designed for fall or winter wear, they might be inner lined with fleece to make it more comfy on a cold day.

champion hoodie

You can pair hoodies with jeans or athleisure bottoms like sweatpants or leggings.


We hope that you have a better understanding on the different shirt designs for street wear. Mix and match and try out different style to figure out the style that most match you.

Streetwear is supposed to be an expression of oneself anyways. Don’t be afraid to take risks with colors, layers, and accessories.

Dress up streetwear style by layering up and adding some accessories. Dress down by wearing them as they are. With their unique designs, less is more.

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