High tops, or “hi-tops”, are sneakers with high shafts that cover the ankles. Some shafts are higher than others but ankle coverage is key. Hi-tops can have an athletic or fashion vibe but are sporty and casual nonetheless. Some look crisp, refined, and polished. Some look tough, chunky and rough around the edges. Some are a hybrid between a sneaker and bootie. You’ll see all sorts of patterns, colours, embroideries and solids with matched or mismatched soles. Closures are typically zippers, laces, or both. Some have strategically placed elastic inserts for easy slip-on and slip-off access. Sometimes there are velcro fastenings too. Fabrics can be synthetic, leather, Gore-Tex, mesh or mixed-media. Linings can be fleece lined and furry for extra insulation. And soles can be grippy, weatherproof, wedged, and platformed.

The collection shows an assortment of hi-tops:

Zappos
Converse Converse
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4
Shopbop
P448 Star Sneakers
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4
Zappos
Sanctuary Sanctuary
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3
Zappos
Sanctuary Sanctuary
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3
Zappos
Converse Converse
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3
Zappos
Vans Vans
$75.00
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4
Zappos
Ecco ECCO
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2
Zappos
UGG UGG
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7
Zappos
Converse Converse
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2
Zappos
Sanctuary Sanctuary
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2
Zappos
Ecco ECCO
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Top Pick
10

The comfort of regular low-top athletic and fashion sneakers is addictive, and thankfully, today’s fashion has made them very versatile. As a result, I’m wearing non-athletic sneakers almost exclusively these days. But low-tops are not sufficiently insulating in cold weather. Low-top sneakers are okay, up to a point, when my ankles are covered by full-length pants or jeans with knee-highs. But what I really need is a pair of cold-weather ankle-covering casual boots that are as comfortable as my regular sneakers. I find exactly that in the right hi-top sneaker.

Five years ago I bought my first pair of leather, fleece lined hi-top Converse sneakers, and haven’t looked back. I find the leather versions especially comfortable, and the furry inners extremely warm. I successfully made them fit my low-volume feet with a few sets of insoles. They work really well in our wet and cold Seattle weather, and to my eye, their iconic urban design looks good with everything. I wear them with straight and flared jeans silhouettes, dressy checked and velvet pants, pantsuits, and wide crops. I also wear them with a few cold-weather midi dresses and skirts but add hosiery for warmth.

Over the years I’ve added more pairs of hi-tops to my footwear capsule because they have taken the place of casual boots. My current assortment is shown in the collection. They are essentials for my style and the most worn shoes in my wardrobe. They magically dress down my everyday dressy and smart casual attire. I keep them very clean so that they look polished with my outfits. It’s extra effort, but worth the crisp and neat appearance.

If I could magically wave my wand and create a blush pink, citron, red, and light blue pair that fit and felt just like the ones below, I would.

You may have many reasons to prefer regular casual booties over hi-tops. By all means, go with what works best for your style. But if you struggle to find anything as comfortable as the right sneaker, and need a warmer alternative to regular sneakers, the hi-top sneaker is one way to go.