I sold thousands of pairs of Hunter boots over my years in retail, and I've watched the brand go through several different moments.
It started with the Original Tall. For years, that was the Hunter boot. Then customers started moving toward the Original Short, followed by the Chelsea as we all wanted something a little easier and more everyday.
Now I'm seeing another shift.
There isn't one Hunter silhouette everyone has to own anymore. Tall, short, Chelsea, lace-up, riding-inspired, quilted—it's less about one trending shaft height and more about finding the version that works with your wardrobe.
And personally? I'm loving where Hunter is going.
THE ORIGINAL TALL
We have to start here.
The Hunter Original Tall Rain Boot is the icon. I sold so many of these over the years, and there's something about the classic black version that still works.
If you want the quintessential Hunter, this is it.
THE ONE THAT STARTED IT ALL. ✓
THE ORIGINAL TALL GLOSS
Same iconic silhouette, but the glossy finish gives it a little more personality.
I included the Original Tall Gloss Rain Boot because it's proof that a classic doesn't have to be boring. It's practical, but the shine makes it feel more like part of the outfit.
THE CLASSIC, WITH A LITTLE SHINE. 🖤
THE ORIGINAL SHORT
This was one of the first big shifts I remember seeing with Hunter.
Customers started wanting something easier than the tall boot, and the Original Short gave you the recognizable Hunter look without quite as much boot.
I especially love it in this deep green—it feels very fall without trying too hard.
THE ICON, CUT SHORT. 🌿
THE PLAY SHORT
This is the more modern short boot in the group.
The Play Short Rain Boot feels lighter and a little more playful than the traditional Hunter silhouettes. It's the kind of boot I'd wear for a farmers market, pumpkin patch, rainy errands or anywhere you're likely to encounter wet grass and mud.
EASY. PRACTICAL. VERY FALL. 🍂
THE ORIGINAL CHELSEA
Then came the Chelsea.
This was when rain boots really started becoming everyday shoes rather than something you only pulled out when it was pouring.
It's easy, understated and works particularly well with today's denim silhouettes.
THE THROW-ON-AND-GO HUNTER. ✓
THE DIANA LACE-UP
This is where Hunter starts feeling less like traditional Hunter.
The Diana Waterproof Lace-Up Rain Boot has that chunky utility-boot feeling that's so good with straight or relaxed denim.
If you want waterproof practicality but don't necessarily want to look like you're wearing a rain boot, this is the one I'd look at.
RAIN BOOT MEETS COMBAT BOOT. 🖤
THE NISSA RIDING BOOT
This is one of my personal favorites.
I've always loved the look of a classic riding boot, and the Nissa Waterproof Tall Riding Boot gives you that equestrian feeling with the practicality you'd expect from Hunter.
The two-tone green and brown makes it even better for fall.
POLISHED. PRACTICAL. VERY EQUESTRIAN. 🤎
THE REFINED QUILTED TALL
And this is the other one that immediately caught my buyer eye.
The Refined Adjustable Quilted Slim Fit Tall Rain Boot feels much more like a fashion boot than a traditional rain boot. The slimmer silhouette and quilted detail make it polished enough to build an outfit around.
Give me these with denim, a sweater and a great barn or wax jacket.
BAD WEATHER. GOOD BOOTS. 🖤
THE DEAR LUCY EDIT
After years of selling Hunter, what interests me most right now is that there isn't one “right” Hunter anymore.
The Original Tall is still an icon. The Short and Chelsea are still incredibly wearable. But the riding, quilted and lace-up styles are giving us completely different ways to wear a waterproof boot.
If I were buying Hunter for the store today, these are the eight I would put on the floor.
And personally, I'm starting with the Nissa Riding Boot and the Refined Quilted Tall.
THE RAIN BOOT IS BACK—JUST NOT QUITE THE WAY YOU REMEMBER IT. 🌧️