Athleisure (Sport-Chic)

Sneakers with dress pants or a track jacket under a blazer—today, these moves are considered wardrobe staples, and many have evolved into the gold standard for modern office attire. But back in 2016, this high-low mixing still felt fresh, edgy, and original.

The Pajama Look

Where exactly does one wear a full pajama suit? That’s a question without a clear answer in 2016 or 2026. Yet, the look was a certified fashion moment, especially when paired with Gucci’s iconic fur-lined loafers. It was an era of maximalism led by the eccentric vision of Alessandro Michele.

Socks with Sandals

A decade ago, we were just starting to wrap our heads around the controversial (yet undeniably comfy) socks and sandals combo. Even now, the debate rages on: is this a legitimate streetwear fit, or should it be reserved strictly for the backyard and quick grocery runs?

The Carabiner

Before the "Coastal Grandmother" or "Grandpa Core" aesthetics took over, carabiners were already dangling from the belt loops of every hipster in Brooklyn. When the trend for this utility accessory eventually dips again, don't rush to toss it—fashion cycles are moving faster than ever, and gorpcore is likely here to stay.

The Silk Neck Scarf

This stylish accessory, which doubles as a way to keep your neck from burning during a Hamptons summer, was a must-have in the 2016 men’s vacation kit. Fast forward to today, and various types of bandanas and scarves are still very much on-trend for adding a pop of color to a neutral outfit.

The Duffle Coat

The toggle coat, with its signature wooden fasteners, fit perfectly into the preppy aesthetic and offered a nice break from the predictable sea of parkas. If you still have a high-quality duffle coat from Brooks Brothers or similar brands in your closet—and it has a slightly relaxed fit—dust it off and wear it with confidence.

The Bomber Jacket

While bomber jackets are now considered a timeless essential, ten years ago, designers were just starting to experiment with the silhouette. We saw a surge in various materials, colors, and intricate embroidery. Specifically, the silk souvenir jacket (or Sukajan) was the absolute "it" item for Spring 2016.

"The bomber jacket has transitioned from a subculture staple to a universal piece of the American uniform, much like the white t-shirt or blue jeans," notes a fashion contributor for GQ.

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