13 stylish rainy-day outfits for looking cute even when it pours

Whether you love or hate a good old rainy day, when the weather is dreary out, it’s easy to feel uninspired fashion-wise or not know how to dress best. But despite what the weather forecast shows, you don’t have to stick to the same old rainy-day “uniform,” and it’s easy to nail a variety of cute rainy-day outfits depending on your mood and plans.

To help inspire some inclement-weather outfit ideas — outside of just a simple raincoat or rain boot — we asked stylists and fashion experts for tips as well as their favorite looks. And the one thing that all the best chic and stylish rainy-day outfits have in common: They’re practical too.

“On a rainy day, you obviously should lean into wearing waterproof fabrics, but I recommend layering pieces that are fashionable yet functional,” fashion expert Melissa Rivers says. “Investing in a pair of sleek, short rain boots that look like your regular ankle boots is a great way to elevate any rainy-day outfit. But you can never go wrong with the classic Hunter rain boots.”

To make shopping even easier, style coach Angela Brown adds that there are three simple things to keep in mind when looking for any fashionable yet functional rainy day outfits:

  1. Fabrics: A water-resistant outer layer is always a plus. “Nylon fibers are both water-resistant and durable — the perfect combo for a stylish rain jacket,” she says. “A polyester blend is also a great choice because of its wicking characteristic and ability to help keep you dry.”
  2. Layers: Wear an outer layer that can be removed and hung up to dry when you reach your destination. “When done correctly, layering will keep you both cute and comfortable,” she says. “With this in mind, you should wear no more than three layers, depending on the temperature.”
  3. Boots: There are so many stylish waterproof boots available these days, that you can’t go wrong with a range of boots on a rainy day. “Between a more traditional, classic tall rain boot, a low-cut bootie and even a lightweight waterproof hiking boot, avoiding puddles won’t be an issue,” she says.

Instead of letting the drab weather get you down, check out these stylist-approved rainy day outfit ideas.

One rainy day outfit idea is straight jeans tucked into knee-high Hunter boots, a classic sweater and finished with a great statement belt. “While I’d still top this off with a longer length coat to help keep your legs dry, a cropped trench coat or bomber would also be practical and look great with this look,” says fashion designer, senior global design director for Gap and founder of Vetted Jamie Lewin. “This outfit is great because it’s stylish, practical and works for anywhere your day takes you.”

Wear a pretty dress with leather ankle or knee-high boots and a trench coat over top. “You’ll look feminine and put together outside and stay perfectly dry when you make it to your destination,” Lewin says. “This is a great option when you want to look a little more dressed up, like for work or a daytime event.”

Pair a neutral yet chic trench coat with water-resistant sneakers and dark skinny jeans. “The trench coat provides protection against the elements while the water-resistant sneakers ensure your feet stay dry and the jeans hide dampness, making it a practical and fashionable choice,” says Stitch Fix stylist Ray Carter.

Let water-resistant accessories and lots of layers bring your rainy-day outfit together. “This ensemble adds versatility with the Three Layer Rule so shoppers can easily adapt to changing weather conditions, making it an ideal choice for unpredictable spring weather,” Carter says.

Contrast a feminine dress with leather accessories for a trendy yet weather-friendly look. “If you want a little bit more than just denim, I love pairing a dress with leather boots and a leather jacket,” stylist Christina Stein says. “This will keep you dry and looking cool.”

Mix neutrals with a pop of color for a stylish yet practical ensemble. “On a rainy day, you obviously should lean into wearing waterproof fabrics, but I recommend layering pieces that are fashionable yet functional,” Rivers says. “A great way to look chic in the rain is wearing a stylish trench coat in a neutral color, but I love pairing it with a pair of colorful rain boots to add a bit of fun.”

Go for a casual chic look and ditch the traditional rain jacket for a statement poncho and boot. “This outfit strikes the perfect balance between style and comfort,” says sustainable style consultant Monica Diaz.

Lean into the sporty vibes instead of the traditional trench coat ensemble. “For those active rainy days, this outfit keeps you comfortable and dry,” Diaz says.

Go for an equestrian twist on the traditional rainy-day outfit. Start with a solid pair of rain boots, then add layers with a bag that can withstand some moisture and complete the look with an elevated raincoat. These are the ingredients to the perfect rainy-day outfit, according to fashion designer and founder of T.Line, Britt Barkwell, who also suggests the splurge-worthy Legres 80 Leather Knee Boots.

Stick to low-key neutrals that you can wear for years to come, from classic jeans to a timeless rain slicker. Darker colors won’t show wear and tear as much, but that doesn’t mean you only have to wear black. Chocolate brown, dove gray and olive green are versatile neutrals that add some dimension too.

For running errands

Embrace the power of a great poncho with leggings and waterproof booties. “I like this look because it checks all the boxes: casual, comfortable, easy, lightweight, versatile and affordable,” Brown says. “On a rainy day, you can throw on a hooded poncho to run errands and not even have to worry about an umbrella.”

“Another option is your favorite pair of sneakers and your favorite sweats, top it off with a fun hat,” Stein says. “It’ll keep you cozy when it’s cold and rainy.”

Don’t shy away from length just because it’s raining. Instead, opt for a duster-meets-maxi-dress look. And you can always accessorize with an umbrella; Brown loves this pretty option that’s just $14 on Amazon.


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