How A Fashion Editor Styles 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 the style set’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.

An oversized shirt earns its place in any seasonal wardrobe precisely because it refuses to behave like one thing. Worn open over a vest, half-tucked into denim, layered beneath knitwear or buttoned up with wide-leg trousers, it can swing from cool girl to corporate weapon with very little effort. As the weather cools, that extra volume also becomes useful territory for layering: sleeves peeking from beneath a jumper, collars sitting over a crew neck, or a crisp hem breaking up heavier textures like wool, leather and corduroy. The best versions feel easy rather than sloppy – roomy through the body, long enough to play with proportions and versatile enough to wear well beyond the first cold snap.

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.