Skip to Main Content
On Trend

Has Menswear Maxed Out The Oversized Trend?

March 29th, 2024

What’s the deal with oversized, big, and baggy clothes these days?

By now, one would imagine that almost everyone has encountered the oversized trend. If you’ve yet to see it in the wild on the street, at the very least you must have seen it via social media. The oversized trend seems to have taken the world by storm in the last two years.

While this article will mainly focus on the oversized trend in menswear, we’ll also touch upon the topic from a more general perspective to better understand the history and some of the potential underlying reasons for the trend to gain such momentum in such a relatively short time.

While in the beginning the oversized trend was more seen in streetwear, it can now be found pretty much everywhere. It has been embraced by high-fashion designers, streetwear, casual wear, sportswear, menswear, and it has even had an impact on classic menswear as we’ve been seeing cuts become more generous and fits and silhouettes becoming looser.

Here’s a look at what we’ll be covering:

  • What exactly is the oversized clothing trend?
  • Why is it currently trending?
  • Is oversized clothing flattering?
  • Where we stand on this trend.

So without further ado, let’s jump right in.

the oversized trend is currently in full force.

Photo via GQ

What is the oversized clothing trend?

The oversized trend does not simply mean that you pick clothes that are a larger size than you usually wear although it may seem so. The oversized trend refers to a style where clothing items are intentionally designed and worn larger than the wearers typical size. This means that you won’t end up with a waist size that doesn’t fit you at all or sleeves that almost touch the ground.

This is not the first time oversized clothing has been trending.

In the early 20th century young ladies began to prefer voluminous and more flowing dresses over corsets that had been the standard up until then.

Later in the 1970s, you could see looser clothing being worn during the hippie movement in the US. These wearers often sewed their clothes themselves and as such weren’t linked to any brands or mainstream fashion at the time.

The oversized trend gained more momentum in the 1980s and 1990s hip-hop era. You could see the likes of Snoop Dogg, Ice Cube, and Tupac wearing oversized t-shirts and baggy jeans and with the huge popularity of rap music during this time the trend spread among youth. It became an increasingly common sight on the streets in many countries.

Hip-hop was not the first instance of oversized clothing being a trend.

Photo via Complex

Today, the trend isn’t associated with any particular subculture and can be seen being worn widely among different groups of people and countries. It also shows no signs of declining as oftentimes can be the case with trends that rise in popularity quickly.

While it might seem that the oversized trend appeared like a strike of lighting out of nowhere, let’s explore a few circumstances that most likely contributed to the continued rise of the trend.


During Covid, most people were confined to their homes at one point or another. When there were no opportunities to leave home, most people started dressing down and wearing more comfortable clothing. Face to face meetings were replaced by online meetings, going to restaurants was replaced by takeout food or cooking at home, and instead of meeting friends for drinks people were binging Netflix. So, there was less reason to dress up.

When restrictions loosened and people could again leave their homes, an increased focus on the comfort of clothes became the driving factor when choosing an outfit. Individuals were looking for styles that allow for ease of movement, adaptability to different body types, and above all the aforementioned comfort.

Body objectification

As social media globally solidified its presence among the everyday life of the majority of people over the past 15 years or so, it has also lowered the barrier of entry to inappropriate commenting and body objectification — especially against women.

Some people argue that wearing oversized clothing is a way to hide your insecurities while others consider the oversized trend liberating as the loosely fitting clothing practically works as an armor against body objectification.

Gender neutrality

Oversized clothing also blurs the lines between female and male fashion which in turn offers a gender-neutral look. Gender neutrality has had an increased focus, especially in children’s education and toys, but also in everyday language, marketing, and fashion for that matter.

There are surely other factors contributing to the popularity of the oversized trend. However, that increased focus on comfort is something that people have always strived for, not just in clothing. With fashion though, Covid may just acted as its most recent catalyst.

The oversized trend has also impacted the classic menswear scene. Even if classic menswear seems to stay more or less the same, if you look closely you do see it follow trends to some small extent. At the moment more roomy fits are popular among the wearers of classic menswear. If you go back a few years the suits were more fitted, lapels slightly slimmer and so forth.

Is Oversized Clothing Really That Flattering?

With oversized clothing being everywhere, the question becomes – is it really that flattering for the wearer? Style and taste are always very subjective and as such it’s difficult to give a universal answer to this question.

If we look at size and fit objectively, it’s generally agreed that clothes that fit the wearer correctly flatter the wearer’s body-type. Clothing that is cut too loose (or tight for that matter) can distort the natural shape of the body making the wearer appear disproportionate and unbalanced. This is also why one specific fit is not going to work with all body types. What may be flattering for one, can be unflattering for the other.

If the oversized clothes make the wearer’s body look unbalanced and the proportions look off, it’s highly likely that whenever this trend falls out of fashion, many will think to themselves how this style of dressing really didn’t look good. But it’s usually the case with most trends when they are taken too far.

Justin Bieber in his infamous oversized suit.

Photo via Today

My Take on the Oversized Trend

In my opinion, there are occasions when oversized clothing looks good but it’s usually when done in moderation. Some people wear the trend well when pairing a slightly oversized t-shirt with a pair of wider fitting jeans that drape nicely.

Nine times out of 10, a well fitting silhouette still looks better than an oversized one. Remember, well-fitting does not mean slim, skinny or tight, but just right. It makes the wearers body look proportionate and well-balanced. If we think about suits, a suit with classic, balanced proportions is, in general, the most flattering kind of suit as it considers its wearers body foremost. If you’re interested in reading more about the subject I recommend Alan Flussers book, “Dressing the Man.”

As a classic menswear aficionado, I can’t help but also point out the impact that the oversized trend has had on classic menswear. Classic menswear is, in general, seen as timeless and, well, classic. However, it does not remain fully static from decade to decade. If you look at how it has changed over time you can see that whatever type of style dominates among the general population at the time has also impacted classic menswear slightly.

During the years while slim and skinny clothing were prevalent, the suits worn by classic menswear enthusiasts were in general slightly more fitted, the jackets were slightly shorter, lapels a bit narrower, and trouser rise was lower.

The slightly more generous fit contributed to garments where the fabric drapes nicer, and a wider group of people who dress in classic menswear can wear suits that have more balanced proportions.

As we’ve moved on to the oversized trend, the fits have become more generous, jackets longer, trousers wider, higher in rise, and so forth. The changes are more subtle, but there have definitely been changes.

Considering the above, I think the small impact of the oversized trend on classic menswear has been a positive one. The slightly more generous fit contributed to garments where the fabric drapes nicer, and a wider group of people who dress in classic menswear can wear suits that have more balanced proportions.

It would be fair to say that everyone is free to dress the way they like as style is subjective and a form of self-expression. However, if you want to develop a style that can stand the test of time it’s worth considering that whatever trend you draw inspiration from, it might be a good idea to incorporate the trends with moderation. This way your outfits are more likely to remain timeless and be something you’re able to wear for years or even decades to come.

Stylishly Yours,

Johan Wikström

Johan Wikström works in data & analytics and is also a classic menswear content creator. He’s always been interested in style, but his journey into classic menswear began in 2019 when he wanted to break loose from the ever-changing cycle of trends and build a timeless and more sustainable wardrobe. Shortly after he started his Instagram account and it grew a bit he was asked to participate in a TV program on national TV talking about sustainability in classic menswear. He was tasked with dressing the TV host using clothes the channel had stored throughout the years from various shows in their warehouse. A fun fact about Johan is that he loves dogs. So much so that his dream job would a to own a dog care center and just spend all of his days taking care of and petting dogs.

All Posts

Edited by Rachel Butler

Featured Image by Mr Porter


London Calling...

Yes, I was there, too. And ya know what they said? Well, some of it was true…