These Classic Boots Were in Style When I Was in High School—Now They’re Back

Growing up in Pittsburgh, Pennsylvania, I saw more than my fair share of rainy days. In fact, Pittsburgh has more rainy days per year than Seattle, so when it comes to dressing for inclement weather, I’m pretty much a pro. Rainy school days, however, were a welcome opportunity to inject a little style into my otherwise bland navy, white, and khaki uniform in the form of colorful accessories.

Back then, I’d reach for my trusty pair of Hunter Boots that I intentionally purchased in magenta to flout my high school’s dress code. Whether wearing them with my pants tucked into the high shaft or paired with tights and a skirt, my Hunter boots not only made a stylish statement but also kept my feet warm and dry. Plus, I found an umbrella to match.

In case you’re not familiar with this particular brand, here’s a bit of background: The British heritage label has been around since 1856 and is recognized worldwide for its signature Wellington-style rainboots, aka wellies. Despite this legacy, Hunter boots had remained something of a cult favorite among the fashion set until 2005 when supermodel Kate Moss was photographed sloshing through the muddy grounds of the Glastonbury music festival in Scotland wearing a gold, micro minidress, and classic black Hunter rain boots. As an impressionable high school student, this was the moment that put rain boots and their styling potential on my radar.

Now, when I know my commute into Manhattan is going to be cold and wet, I find myself skipping my usual Chelsea boots in favor of a new pair of Hunter Boots. And it’s evident that I’m not alone. I’ve spotted Hunter rain boots on several fashion influencers that we know and love, plus IRL in the city. So although fall and winter weather in the Northeast doesn’t always lend itself to outfits featuring boots with miniskirts, there are still several ways to style Hunter boots that look almost as cool as Kate Moss.

Keep scrolling for seven outfits with Hunter boots that will inspire you to dig your wellies out of the closet or swap your old combat boots for a shiny (or matte) new pair of rain boots. Plus, one last pro tip: Hunter boots are literally the only shoes that keep my feet 100% dry when traipsing through NYC’s wet, snowy, slushy winter streets. With snow storms on the horizon, you bet I’m bringing my Hunter rain boots back into regular rotation.