Tommy Hilfiger Karissa Rain Boot
Durable and chic, these classics will be your go-to for years to come. The fun print adds an unexpected pop that works great with leggings or skinny jeans, and the zipper and buckle detail add a little equestrian appeal.
To buy: $80; dsw.com.
Melissa Shoes Francoise + Jason Wu Boots
Fend off dreary drizzles with these fun wellies. A sophisticated shade of blue plus an adjustable buckle give this pair an unexpected edge. Available in three other colors.
To buy: $73; 6pm.com.
ASOS Game Chelsea Wellies
Never let downpours put a damper on your evening plans again—these sparkly booties will have you wishing for cloudbursts more often. Wear them with your favorite LBD for a rainproof, cocktail-ready look.
To buy: $31; asos.com.
Jeffrey Campbell Stormy Rain Booties
There’s no need to sacrifice style with this wet-weather take on the traditional Chelsea boot. The timeless design gets a rubber makeover, keeping you dry—and on trend.
To buy: $55; shopbop.com.
UGG Shaye Rain Boot
The experts in warm, fuzzy winter boots also know a thing or two about rain—thick rubber and a natural wool lining will keep your feet as cozy and dry as the brand’s iconic après-ski styles. Available in four other colors.
To buy: $80; nordstrom.com.
Hunter Refined High Heel Chelsea Boots
Think of these heels as your trusty rain boots, only incognito. A slip-proof lug sole and sleek rubber construction mean you can walk straight off the sodden sidewalks and into the boardroom without stopping to change your footwear.
To buy: $195; zappos.com.