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.  

Shop Outfits With Hunter Boots

1. London Calling
7 Stylish Hunter Boots Outfits for Women



Go all in on the London look by pairing Hunter boots with a long houndstooth coat and simple accessories.

Your favorite jeans will do just fine.

The Balmoral style features a lugged sole for grippy traction.


Sunglasses are for rain or shine.

2. Florals for Spring
7 Stylish Hunter Boots Outfits for Women


3. Red Hot
7 Stylish Hunter Boots Outfits for Women



Choose a bright pair of Hunter boots and build an outfit around them.

Tights often pair nicely with wellies. 

Hunter's glossy boots come in several eye-catching colors.

Try matching your boots to your bag—bonus points for the umbrella, too.

4. The New Prep
7 Stylish Hunter Boots Outfits for Women



You can take the girl out of prep school…

J.Crew sweaters are an essential party of any preppy look.

One can never have too many Oxford shirts, IMHO.

BRB, getting my hands on this Killing Eve collab before they sell out.

Simple jewelry helps make any outfit feel more complete. 

5. Back in Black
7 Stylish Hunter Boots Outfits for Women



Hunter's lace-up commando boots are edgier and look great with a leather moto or bomber jacket.

Bomber jackets always look badass. 

6. Easy Everyday
7 Stylish Hunter Boots Outfits for Women



Evidence that Hunter Boots are a great everyday shoe that can be worn with almost any casual look.

Who What Wear editors swear by Agolde jeans. 

The neoprene shaft of these over-the-knee boots will easily slip under a pair of bootcut or straight-leg jeans. 

7. Stay Golden
7 Stylish Hunter Boots Outfits for Women



We love variations on a color theme, so don't be shy about building an entire outfit around your favorite Hunter Boots. 

Another perfect winter puffer coat—it's on sale, too.

We love a wide-leg trouser moment in all seasons.

If you're down for the head-to-toe look, don't forget to coordinate your socks.

Hunter Boots's version of a statement shoe, obviously.