Glamour reviewer and self-proclaimed Vans enthusiast Holly Ryan has a pair of these Y2K-esque high-tops. “They’re similar to the classic Sk8-Hi, but they don’t have cushion around the inside of the ankle,” she says. “This gives them a slimmer look, to counter the chunkiness of the platform. They’re comfortable and easy to style with just about anything. I prefer them casually with slightly cropped jeans.”
Best Unisex: Vans Sk8-Hi Shoe
Vans aren’t just for skateboarding, and with the Sk8-Hi style you don’t have to differentiate between men’s high-tops and women’s shoes, either. What started as a skate-park staple has evolved into one of the coolest unisex styles in streetwear. They’re grungy and playful, and the padded collar makes them comfortable and surprisingly supportive. With their signature jazz stripe, lace-up closure, and reinforced toe caps, these high-tops are never going out of style.
“I love these black sneakers with a cropped, wide-leg pant or jeans, but they can also look great with shorts or a skirt,” says Ryan. “They’re comfortable for walking and don’t take time to break in.”
Best Retro: Saye Modelo ’89 High-Top Sneakers
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Saye Modelo ’89 High-Top Sneakers
With a throwback design straight out of the ’80s, these high-top sneakers are oozing with nostalgia, yet they are entirely on trend. Perhaps it’s the minimal silhouette or the clean colors, or even a combination of both, but these shoes are infinitely versatile. They’ll pair effortlessly with a T-shirt and jeans, a flowy, summer dress, or even sporty athleisure wear. Plus, they’re vegan-friendly, a true sign of the times that betrays the retro aesthetic.
“I purchased these as an alternative to the Blazers, and I really do love the look of these,” wrote one reviewer. “The only thing I will say is that if you lean more toward having to purchase wide shoes, these are quite narrow. But the look and feel are incredible.”
Best All-White: Reebok Freestyle Hi High Top
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Reebok Freestyle Hi High Top
One of the most iconic high-top sneakers of all time, the solid white Reebok Freestyle Hi is a perennial favorite among everyone from dancers to children to hard-core sneakerheads. They were originally introduced in the ’80s as an aerobics shoe, and to this day they remain one of the most fashionable high-top shoes of all time. They’re not just cute, they’re comfortable, too, featuring padded foam insoles, secure lace-up closures, and an abundance of arch support.
But don’t just take our word for it. “I absolutely love these shoes. I’ve been wearing them since I was in my 20s and I am now in my 70s,” wrote one Zappos reviewer. If rebuying the same style of sneakers for 50 years isn’t a testament to their enduring relevance, nothing is.
