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These Cute Ankle Rain Boots Make A Gray Day Feel Less Miserable

They’re all practical styles, too.

Updated: Dec. 18, 2022

Originally Published: Aug. 22, 2021

Spencer Wells

Rowing Blazer x Hunter Boot collaboration

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Rain boots are a non-negotiable wardrobe necessity. Even if you live in an area where rain is rare, you’ll still want a pair of durable, water-resistant shoes in your footwear collection on the off chance the weather takes a wet and gloomy turn. Once you’ve accepted that they’re a true must-have, the conversation then pivots to what style of waterproof boot do you choose. Do you go for a classic, knee-high galosh reminiscent of your mom’s gardening outfit? Or, do you opt for a silhouette with a bit more styling versatility like, say, a pair of women’s ankle rain boots? If you feel yourself gravitating towards the latter, you’re in luck. Ahead, you’ll find a list of such refined yet functional shoes that offer both fashion and function elements.

The booties featured below run the style gamut. Some, like Bottega Veneta’s cartoon-esque Puddle boots, offer a dose of eccentric flair that will brighten up even the grayest of days. The outlandish, “ugly” boots are also likely a mainstay on your Instagram feed, courtesy of in-the-know fashion influencers you follow. Other shoes included ahead feel a bit more wearable in an everyday setting. For example, Italian luxury shoe brand Tod’s offers a pair of rain boots made from waterproof leather, which could easily pass as your standard hide bootie.

Scroll on to shop the 20 most stylish ankle rain boots. They will be your sartorial saving grace when the forecast calls for rain.

Rowing Blazer x Hunter

Chelsea Rain Boots

$195

Rowing Blazer founder Jack Carlson celebrated his love for his Hunter wellies by partnering with the footwear label on a capsule collection. As seen in this rain boot, the design combines Rowing Blazer’s distinctive patterns with Hunter’s beloved shoe silhouettes.

Bottega Veneta

Puddle Ankle Boots

$820

Bottega Veneta’s Puddle boots have a cult following of fashion fans who can’t get enough of the “ugly” shoe. They’re surprisingly versatile as you can even wear these on non-rainy days with a skirt and sweater.

Tommy Hilfiger

Ankle Rain Boot

$109

The boots will give a cheerful pop of color to your all-black, rainy-day outfit.

Stutterheim

Chelsea Rainwalker Navy

$175

$88

If you’re new to the rain gear scene, you’ll want to check out beloved brand Stutterheim first. The label specializes in waterproof pieces and has the cutest ankle booties that’ll keep you dry during torrential downpours.

Aigle

Versatile Ankle Rain Boots

$130

If you love French women fashion, then opt for an ankle rain boot that’s handmade in France. This one from Aigle features a low heel and is completely waterproof, so jump in those puddles if you want to.

Moncler

Ginette Wool-Trim Rain Boots

$400

Since Moncler is known for its alpine clothes and accessories, you know the rain gear, too, will keep you dry in the harshest storms. These Ginette booties feature a rib-knit trim and a rubberized patch for that subtle touch of logo mania.

UGG

Drizlita

$90

If you miss your yellow booties from childhood, purchase the adult version from UGG. This boot is suitable for trekking through rain and snow storms.

J.Crew

Short Lug-Sole Rainboots

$85

$70

These green lug-sole rain boots from J.Crew are more interesting than a simple black pair yet still equally wearable. Style with your favorite pair of jeans or with a tiered mini dress for an interesting contrast of soft and utilitarian aesthetics.

Loeffler Randall

Davey Black/Terracotta Quilted Boot

$450

Even if your version of a hike is leaving your apartment in the middle of a downpour to make a snack run, these quilted, water-resistant Loeffler Randall boots still belong in your closet.

Sorel

Brex Heel Chelsea Bootie

$180

For a rain boot that doesn’t look like a rain boot, opt for this pair from Sorel, which features a high heel. Your feet will stay completely dry thanks to the waterproof leather.

Burberry

Vintage Check Neoprene and Rubber Rain Boots

$470

Burberry’s signature plaid print is a classic. Add a small touch of the recognizable pattern to your outfit with these black rubber boots from the British fashion house.

MSGM

Lug-Sole Ankle Rain Boots

$282

$202

You don’t need to wear head-to-toe pink to channel the Barbiecore fashion trend. Simply slip on these boots and — voilà — you’re all set.

Tod's

Ankle Boots In Leather

$795

Sometimes you want the rubber look when it comes to your rain-resistant galoshes. And other times, you want to slip under the radar with a professional, everyday bootie. Enter Tod’s waterproof ankle rain boots.

Baxter Wood

Grey Sole Hevea Chelsea Boots

$125

These minimalist Chelsea boots from sustainable brand Baxter Wood are made of natural rubber derived from trees. Style them underneath your gray work trousers or with a black jumpsuit for a monochromatic look.

La Canadienne

Kyree Leather Boots

$550

These may look like your run-of-the-mill Chelsea boots, but the shoes are actually made of waterproof leather. You can confidently wear them in a rainstorm while knowing the weather won’t damage your footwear.