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How to Style an Oversized Shirt for Every Occasion

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 top — 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

COPENHAGEN DENMARK  AUGUST 05 A guest wears a white buttonup shirt with black vertical stripes featuring a classic...

Edward Berthelot/Getty Images

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.

White Mixed Stripe Oversized Shirt

Genevieve Pleated Wide Leg Trouser

2. As a crop top

COPENHAGEN DENMARK  AUGUST 04 A guest wears yellow maxi skirt yellow and brown stripped long sleeve top outside Bonnetje...

Raimonda Kulikauskiene/Getty Images

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Writers at Lord’s Press come from a range of professional backgrounds, including history, diplomacy, heraldry, and public administration. Many publish anonymously or under initials—a practice that reflects the publication’s long-standing emphasis on discretion and editorial objectivity. While they bring expertise in European nobility, protocol, and archival research, their role is not to opine, but to document. Their focus remains on accuracy, historical integrity, and the preservation of events and individuals whose significance might otherwise go unrecorded.

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