Is It Better to Be Over- or Underdressed?

This reminds me of a “Saturday Night Live” parody of “Hamlet,” where a host might dramatically ask, “to overdress or underdress, what should one choose?” while theatrically clutching at their attire. Indeed, opinions on dressing are distinctly polarized.

On one end, followers of the Coco Chanel doctrine advocate for simplicity. The renowned French fashion icon famously advised always opting to be underdressed, famously declaring, “Elegance is refusal,” and suggesting, “Before you leave the house, take one item off.”

Conversely, proponents of Iris Apfel, the late style maven, subscribe to a philosophy of abundance: more patterns, more accessories, more enjoyment. This view is shared by fashion designer Christian Siriano, who recently designed Oprah’s purple suit for her Democratic National Convention address. “Being overdressed is better than the alternative,” he remarked during our conversation. He confessed his penchant for opulence, stating, “I adore the glamour, and for me, there’s rarely an occasion that’s too casual, unless you’re poolside or on the sand.” Even then, he argues, one should sport “an extravagant hat and handbag.”

Choosing between over- or underdressing, however, transcends objective comparison; it’s about personal fit. Each option might draw attention, so it’s crucial to decide if you prefer to be noticed for excess or informality. Ultimately, the key to appearing appropriate, regardless of the expected attire, is confidence.

Yet, there exists a third path, epitomized by the Balenciaga approach under Demna’s direction. This style mimics everyday wear, like jeans and T-shirts, but is executed with haute couture craftsmanship and materials. A prime example is Balenciaga’s recent couture line, which featured seemingly worn concert T-shirts that were actually intricately hand-painted by artist Abdelhak Benallou, depicting the fashion house’s staff as a rock band.

This trend, often termed “stealth wealth,” includes items like Loro Piana’s cashmere baseball caps and upscale denim and chore jackets that populate many fashion labels. It’s a sly nod to casual that masquerades as mundane but is anything but, offering an air of effortless sophistication that belies the meticulous design and high cost that underpin it. This approach allows for a luxury that looks understated yet distinctly refined, though it comes at a premium. Deciding whether it’s worth the investment is a personal choice.