Vans’ Retro-Styled New Release Blends Y2K Vibes with Modern Materials

For those of us old enough to have worn puffy shoes in their late ’90s heyday, this reissue will evoke plenty of memories.

Close-up of a gray suede sneaker with black leather accents and a gray rubber sole.

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By Hayley Helms

Published January 7, 2026

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Updated January 7, 2026

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Flat sneakers may be having a moment, but Vans’ latest archival reissue is proving puffy styles have their place too.

Anyone who laced up chunky sneakers in their late-’90s prime will recognize the Upland.

Pair of brown suede sneakers with navy blue accents, burgundy lining, and blue laces on a light background. — If one didn’t know better, this upgraded Upland could be straight from the year 2000.

Now, the style is even better, due to the addition of new comfort-driven materials and fresh colorways.

Modern throwback

Although its looks are reminiscent of the chunky skate shoes that dominated the late ’90s and early 2000s, the Upland has managed to stay fresh since its initial reissue in late 2024.

It enters 2026 with two new winter-ready colorways.

Pair of brown and navy Vans sneakers with blue laces, one showing top view and the other showing sole. — The rich Dark Brown colorway is right on trend.

The retro-inspired Upland retains its original DNA, including the wide laces, puffed-up tongue and padded collar, but brings some notably modern tech to the table.

Pair of gray and black suede sneakers with gum rubber soles and black laces on a light background. — The new Dark Grey color is fashion-forward, past or present.

That includes additional underfoot support, as well as elevated, textured hairy suede in the upper and Cupsole construction, which lends more durability to the style.

The leather overlays on the sidewall in the form of the heritage “Flying V” logo add tactile and historical depth.

Gray and black suede sneaker with black laces and gum rubber sole on a beige background. — The leather “Flying V” logo nods to the Upland’s heritage.

For 2026, Vans has given the Upland a new look with a pair of fresh colors: a moody Dark Grey and a warm Dark Brown, both on-trend for this winter season.

Availability and pricing

The Upland is available now on Vans’ official website, retailing for $100.

Brown suede and navy blue sneaker with burgundy accents and a gum sole, side view.

Vans Upland

$100 at Vans

About the Author: Hayley Helms is an associate editor at Gear Patrol specializing in outdoor gear. Once upon a time, she wrote for Men’s Journal, Gearjunkie and Shape. Whether it’s testing a new rain shell or putting a pair of hiking boots through its paces, she leaves no stone unturned (however, she always Leaves No Trace).

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