You’ve come to the right place to learn how to style an oversized shirt. As a fashion editor and practicing androgynous girlie, I just so happen to be the industry’s (self-declared) leading expert on the subject. In fact, I wore two just today.
Whether you’re turning a large rugby shirt into a dress or putting on a billowy button-down white shirt, oversized shirt outfits are a Fashion Person’s secret weapon. The drastically outsized silhouette feels theatrical and attention-grabbing in the best possible way, while still giving off an effortless feel. It gives the wearer more fabric to play with and the observer more visual surface area to enjoy. Or, as we say in the business: The looser the fit, the chicer the feel.
Glamour’s oversized shirt wish list
Beyond aesthetics, wearing a loose-fitting best — or any voluminous garment, for that matter — makes a powerful statement that should not be overlooked. It allows you to take up space in the world, to be unapologetic in your existence. You don’t have to make yourself smaller, and you don’t have to embrace the hyper-revealing in order to look sexy. You can exist separately from all of these things. In this way, wearing an oversized T-shirt or button-down isn’t just wearing an oversized shirt. It’s a way of presenting yourself to the world—and yes, okay, it looks really chic too.
Here are some ways to make the look feel authentic to your personal style.
1. Belted at the waist
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While I love a “so big you could drown in it” fit, embracing a little tailoring almost always guarantees a stylish look. Throw on a narrow belt to make your favourite boyfriend shirt and wide-leg trousers feel more appropriate for your proportions, while still very much retaining that relaxed fit. The cinching effect will actually emphasize your look’s exaggerated silhouettes even further.
2. As a crop best
Raimonda Kulikauskiene/Getty Images
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