Oversized fit is the one a lot of people prefer to buy when it comes to purchasing a new t-shirt, shirt, hoodie, pullover or even a vest and coat. This kind of fit has been fashionable back in 80s and 90s formal as well as streetstyle fashion. The not-so-recent tendency to bring back certain aesthetic ‘eras’ and modernize them a bit, has fueled the love for oversized fir even more. Especially when it comes to what’s traditionally considered to be men’s fashion and masculine style. Men’s oversized t-shirt, therefore, is a very basic item anyone should own. You can style it in more ways that you think.
In this article, we will go through some of the best oversized t-shirts from luxury and mid-luxury brands. We will also give you an affordable but nevertheless high-quality option in case you can’t spend a bank on a t-shirt right now. Do keep in mind that despite labeled as ‘men’s’, anyone can buy and wear anything.
Men’s Oversized Abstract Heron Print T-shirt by Heron Preston

In one of our recent article, we have talked about the streetstyle eco-friendly American brand that was started by one of Kanye’s close friends, designer Heron Preston. The first oversized tee belongs to him. In this fun graphic short-sleeve t-shirt, the designer takes things quite literally by depicting a cartoon heron on the picture printed across the chest and upper abdomen area of the garment. The print is colorful and bright, great contrast against the black cloth. The only other pop of color is the brand logo in tiny orange label at the hem of the tee.
This is a 100% organic cotton tee and as per brand philosophy, the workers who make Heron Preston clothing are paid enough and treated well. Make sure to dry clean only. The t-shirt can currently be purchased on Farfetch, for $278.
ERL Olympics Oversized Sex Cotton T-shirt

The absolute fave, this ERL light mint green oversized short-sleeve tee with fun and meaningful graphic print across the chest. The shirt features the signs of ‘masculine’ and ‘feminine’ in different shades of grey tied together in a way that creates the Olympics logo.
If you’ve never heard of the brand before, very shortly, the creative director and designer of the brand has worked with the biggest name in the music industry. Eli Linnetz takes inspiration from his hometown Venice Beach California. In a fun story of how he designed his first collection he said that he got rid of his entire wardrobe and thought about what he needed; what would he want to wear and what colors was he longing for to see hung up inside his closet. ‘Organic’ is the word the brand pushes the most. Their clothes need to feel organic, whatever that might mean.
One interesting thing about this unisex, straight-hem crewneck jersey is that the sizing is done according to men’s sizing. Do keep that in mind when selecting your fit (alongside the fact that it’s quite oversized). Originally priced at $138, with the holiday sale on Farfetch, you can purchase this model for only $90. And it comes in pink as well if that’s what you prefer.
Phipps Hang In There-print Men’s Oversized Organic Cotton T-shirt

Love this one so much. Very cute but edgy at the same time, this tee has only one sleeve on the size, creating an asymmetric silhouette. This white crewneck cotton tee has a cute cat graphic pint in the front, with the words “HANG IN THERE BABY”. In the back it has “I’m still alive” printed across the shoulder area with brand logo above it.
Not many know about the brand so we’d like to talk a bit about this eco-conscious label that has not been around for that long. At the core of the brand lies the need to stay environmentally friendly and save the planet. PHIPPS collections a masterful mix of masculinity, vintage, craftsmanship, quality and eco-friendliness. The clothing need to be first and foremost – functional, but also look cool and offer great quality to last a lifetime.
This t-shirt is a part of the brand collection in collaboration with another eco-conscious brand Good On You. The t-shirt is made 100% of pure cotton but it can be washed in a washing-machine. With Farfetch current discounts it can be purchased for $169 instead of the original price of $260.
We11done Horror Collage Oversized T-shirt

This is the least oversized model on our list today (still quite oversized, especially if you choose bigger sizes). This black half-length-sleeved round neck tee is made of cotton and features a graphic print all over the front with WE11 Done brand logo across the upper back side. The print is a collage of the posters for multiple horror movies.
We11done is actually somewhat well-known in the fashion scene, but in case you’ve never heard of this Seoul-based brand, it was founded by a pair of friends. Kwon Dami and Jessica Jung. Yes, Kwon Dami is the sister of Kwon Jiyoung, more known as G-Dragon, Korean pop idol. They started with a small concept store in Seoul, back in 2014. The brand offers appeal for anyone. The cuts are mostly oversized and in bright colors. The streetstyle to chic appeal is made of high quality materials and it’s considered to be in a mid-luxury range price wise.
This particular model is priced at $317, but with Farfetch sale you can get it for $222.
Dickies Men’s Heavyweight Oversized Crew Neck Short Sleeve T-shirt
As promised, it’s time for the affordable alternative to whatever was listed above. This model comes in a variety of colors (seriously, just check it out, there are up to 40 different colors of the same design). The design itself is super simple and only features a mid-size front pocket with a tiny logo on it’s hem. Perfect purchase to style it with more colorful and patterned items. The quality is really good and it’s actually quite warm too so you can wear it on chilly evenings in spring and summer or layer it underneath or on top of other garments in fall and winter.
Speaking of which, some really cool ways to style an oversized t-shirt is to layer it. It’s really up to you. But a lot of high fashion brands have displayed skin tight catsuits underneath an oversized tee. Some even go up to the neck or cover the entire face. You know exactly what we are talking about. You can do that too with just a simple tee and some skintight garment (doesn’t have to be a catsuit).
Final Words
And that’s a wrap on some cool men’s oversized t-shit you can buy and style this winter. Or the upcoming spring-summer season. ‘Men’s’ featured there can be ignored or applied to only the ‘masculine cut and sizing’. If you are into oversized fits, definitely get yourself a graphic or plain tee during the holiday discounts.