Few menswear staples have the staying power of a great denim or chambray shirt. It's a piece that's as comfortable in the city as it is in the countryside, equally at home layered under a suit jacket as it is thrown on over a T-shirt. Rugged yet refined, it's the kind of shirt that feels broken-in from the start but only gets better the more you wear and wash it. Whether you favor the hearty weight of traditional denim or the softer drape of chambray, both fabrics bring a dose of casual cool to any outfit without ever feeling sloppy.

What makes this shirt such an enduring favorite is its ability to evolve without losing its core appeal. Over the decades, it's been reimagined in slimmer silhouettes, washed in lighter hues, adorned with Western yokes or stripped back to minimalist perfection. Today's best versions have a more relaxed, boxy fit and bridge workwear grit with understated sophistication—which explains why the shirt is as relevant now as it was fifty years ago. They honor that heritage while taking advantage of modern fabric innovations and styling versatility—the real question is which one is right for you? We've pulled our favorite options in a range of styles, washes and, of course, price points.