Model styling light green oversized check shirt

It’s common knowledge that fashion goes in cycles, and some 25 years after something goes out of style, it’s likely to find itself embraced by a new generation. The trend for oversized clothing is no different, whether you’ve been inspired by the early 90s rave scene, hip hop culture, grunge, or right through to what's on display on the modern day runway, oversized clothing is everywhere.

At North Workshop, you can find a huge range of vintage oversized men's and women's shirts and t-shirts from our extensive range of unbranded and across all of your favourite brands, including the undisputed king of the prep turn cool, Ralph Lauren. But whether you’ve long been a fan of oversized, want to cover up that winter body, or are simply just interested in how the look works, we’ve put together everything you need to know about wearing vintage oversized shirts in the name of fashion.

How to wear oversized shirts for men

Don’t let them swamp you

Even when it comes to oversized men's shirts, there’s still such a thing as too big. The key thing is to make sure that, whatever you’re wearing, the garment still retains some sense of form and definition. “You want the items to be oversized in the correct places, like the shoulders and the waist,” celebrity stylist Sarah-Ann Murray explained to Fashion Beans. “Otherwise, you’ll look like a schoolboy who’s not grown into his new school uniform yet.” To choose an oversized shirt that still offers some definition, size up a one or two sizes up from your usual fit to make sure that it hangs well off your shoulders.  If this means that the sleeves will then be too long, consider turning the cuffs back on themselves to shorten the length.

Male model wearing a cream oversized shirt

Choose something which goes well even in smart casual

Despite the excessive size, an oversized men's shirt can still work in a more formal context over fitted underlaid t-shirts and high waisted trousers, or tucked in to accentuate a shorter torso with longer legs. Likewise, if you’re looking for something to wear over your oversized shirt, particularly in longline styles which extend far past your waist, a more fitted jacket can actually help to smarten your outfit up, and draw attention upwards in a way that can actually give you a slimmer-looking figure overall.

How to wear oversized men's t-shirts

When it comes to oversized men's clothing, the biggest trend of all in recent years has been the rising popularity of oversized men's t-shirts. All those baby photos that get dug up every Christmas of you in what is now considered a vintage t-shirt have come back in trend, taking away from tighter silhouettes and widening the torso. To style oversized t-shirts, the trick is to avoid a rectangular silhouette, but by all means don’t revert back to them skinny jeans which were cool in 2012.  A classic straight leg cut on the trousers will complement the broad shouldered oversized look you’re sporting on top.

Model wearing oversized green check shirt

How to wear oversized shirts for women

Don’t be afraid of tucking or tying

Oversized women's shirts — which, when you buy them vintage, are often men's shirts to begin with — have a tendency to look even bigger than the label suggests. This means that the easiest way to style them is by simply tying the bottom into a knot, which works if you’re wearing it as an overshirt or on its own. 

Forget about trousers or leggings altogether!

While men have to worry about keeping their oversized shirts from looking like a dress, that’s not going to be a problem for any women trying to style their baggy outerwear. A longline shirt in a plain colour can actually function as a great substitute for a dress, and with so many styles to choose from, you can just pick the length and fit that you’re most comfortable in. 

Image source: Pinterest


How to wear oversized women's t-shirts

Unlike baggy men’s t-shirts, the rules about how to wear an oversized ladies’ tee are pretty similar to wearing larger shirts, they work brilliantly as dresses. Alternatively, you can just rock the shirt as if it’s fallen straight out of your Dad’s wardrobe, and team it up with a pair of beat up Levi’s, a look celebrities such as Hailey Bieber continue to pull off effortlessly.

November 10, 2020 by Ryan Fidell