Dad Shirts Are the Key to Dressing Effortlessly Cool in Spring 2026

Dad shirts are that find that seems like an accident, but ends up being destiny. They weren’t born to be trendy or seeking approval; they were simply there, waiting to be stolen from the family closet. They have the structure of the past and the attitude of the future. Slightly oversized, perfectly imperfect, with that “I just threw them on without thinking” energy that actually requires a discerning eye and a well-honed confidence.

Dad shirts are ideal to wear with your favorite jeans, skirts, and trousers for a stylish look in winter and spring 2026. They’re the perfect blend of classic and irresistible. With them, there’s nothing to prove: simply button them up, roll up the sleeves, and let them do the talking. And each style has its own character: from the intellectually melancholic professor to the heir who’s never ironed a garment.

Here are six shirts, six stories, six ways to make the everyday dad shirt sophisticated.

1. Academic with a sense of humor.

To look a professor who forgot the classroom and decided to dress in style, break up the seriousness of your look with an unexpected detail—the kind of accent that transforms a simple garment into something with character. Finish the look with dark blue straight-leg jeans and loafers, or tuck it into a white linen midi skirt with sandals.

2. A linen shirt evokes eternal vacation.

In Munich, Germany.

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