10 Rainy Day Outfits for 2024

I almost always start with my shoes when I’m getting dressed for a rainy day, since they’re the most limiting component of the outfit, so I’ll be speaking to my shoe choices a lot in this post. Beyond that, you can really wear anything you want, as long as you have an appropriate coat to throw on top.

Speaking of which, not all of these pictures show the coat I was wearing, but I almost always wear some type of water-resistant coat when it’s rainy or drizzling outside. I’ll do a roundup of my favorite rain-friendly jackets at the end of this post.

#1. This outfit is just a simple sweater and jeans with ankle boots, and a trench coat on top to elevate the look. I wore this to a casual dinner with Paul one rainy night a few weeks ago.

Waterproof suede boots are really convenient to have when you live in rainy climates. The pair I’m wearing here are Aquatalia, but Blondo also makes waterproof suede, and I’m sure there are other brands that do too.

similar trench // Everlane sweater (S) // MOTHER denim (29) // Aquatalia boots (8) (similar) // Coach bucket bag

#2. This outfit features a bonafide raincoat! And I’m wearing Blondo waterproof suede boots.

Yes, my jeans are long, so they may not be ideal for torrential downpours and sloshing through puddles. You can easily swap them out for ankle-length jeans, if that’s a concern, but if it’s just drizzling, which is what it usually does here in Philly, they’re fine.

My purse choice also comes into play when it’s raining outside. I don’t like to carry my softer leather bags, or anything suede or microfiber lined, but this Coach pebbled leather shoulder bag is perfect.

Helly Hansen rain jacket (M) // Vince sweater (S) // MOTHER denim (29) // Blondo Waterproof boots (8) // Coach shoulder bag

#3. This is another outfit with the Blondo waterproof boots, and these jeans are a little shorter, which is better when it’s really messy out.

I’m carrying a faux leather bomber jacket, which can be fine in the rain, if you have an umbrella. I like a clear plastic umbrella or solid color that coordinates with my coat. Or a practical hooded raincoat would work with this outfit too.

Relaxed Forever Cozy Fair Isle Sweater (S) // High Rise Vintage Slim Jeans (28) // Blondo Waterproof boots (8) // Vegan Leather Bomber (S) // Madewell bucket bag

#4. I realize this outfit is super simple, but it’s easy and practical, and the colors and proportions work nicely together. And yes, I wore a coat on top – I have a The North Face short trench (something like this) that’s my go-to for casual rainy day outfits.

These Paul Green Chelsea Boots are great for rain and icky conditions because not only do they have a water-resistant upper, the thick lug sold provides traction on slippery surfaces.

I actually wore this outfit in a downpour, and ran across a soggy, grassy meadow to get to my car, and these boots still look like new.

Jenni Kayne sweater – 25% off (S) // MOTHER denim (29) // Paul Green boots – 35% off (8) // not shown – The North Face City Breeze Rain Jacket

#5. When it’s chilly, a puffer jacket can double as a rain jacket, and these are the same Paul Green boots I spoke to above.

Gap Factory puffer (S) // v-neck sweater (S) // straight leg jeans (29) // Paul Green boots – 35% off (8) // Coach bucket bag

#6. This date night outfit also works for a rainy day because the Marc Fisher boots are a hard, glossy leather that doesn’t soak up any water and easily wipes clean if I happen to step in a mud puddle. (They’re also 30% off right now!)

I wore a pair of flares and a cute top, and then I topped it all off with my black leather bomber jacket. I have some leather jackets that are too delicate to wear in the rain, but this one holds up really well. I just needed an umbrella to get from the car to the restaurant.

leather bomber (S) (budget option) // v-neck sweater (S) // PAIGE denim – $50 off (29) (budget option) // Marc Fisher boots – 30% off (8) // J. Crew earrings – 25% off // necklace – 50% off // Capital Z crossbody

#7. Here’s a casual look I’ve worn in a few iterations when I had to be out and about in the rain. These Steve Madden Chelsea Boots are also a glossy, hard leather that holds up to the elements without being specifically waterproof.

And this Helly Hansen rain coat is perfect for colder rainy days because it has some insulation. Plus, I love the pop of color against a neutral outfit.

Helly Hensen Lisburn Rain Jacket (M) // Treasure & Bond sweater (S) // AG Jeans (29) // Steve Madden Chelsea Boots (8) (also at Zappos) // Madewell bucket bag // necklace

#8. These Tory Burch Chelsea Boots are yet another example of a hard leather bootie that you can wear in the rain. This is why I don’t even bother owning rain boots. I have plenty of stylish options that work just as well.

This Everlane Renew Anorak is a nice jacket for spring and fall, and it comes in several colors.

Everlane Renew Anorak (S) // old black sweater // similar Paige Cindy jeans – $50 off (29) // Tory Burch Chelsea Boots (8)

I also wore those boots with bootcut jeans and a simple sweater to meet a friend for lunch on a rainy day last month. I wore my The North Face rain coat on top.

Gap sweater (S) // MOTHER denim (29) // similar Tory Burch Chelsea boots (8) // similar pendant // similar hoops // not shown – The North Face City Breeze Rain Jacket

#9. And there’s no reason why you can’t wear leather sneakers when it’s rainy outside. Again, I wouldn’t necessarily wear them in a downpour, but when it’s sprinkling, they’re fine. And a lot easier than boots.

I wore this to a casual live music venue one rainy Saturday last month.

line and dot top (S) // Fidelity Cher (similar option) // similar P448 sneakers (39) // LOFT earrings // not shown – The North Face rain jacket

This is a similar outfit; I guess I’m even wearing the same jeans! But I thought I’d throw it in here, since I wore it in a rainy day recently.

Rails cardigan (S) (on sale at Bloomies) (budget option) // Fidelity Cher (similar option on sale) // P448 sneakers (39) // similar pendant // Jenny Bird earrings // Coach shoulder bag (option)

#10. Finally, I know I said this post was casual outfits, but when you need to level it up and want to wear a dress in the rain, waterproof knee boots are your friend.

These Blondo knee boots are a waterproof suede that holds up to pretty much any type of inclement weather, and they look great with dresses. I would wear a trench coat on top of an outfit like this.

sweater dress // waterproof knee boots (similar at Zappos)

I hope that’s helpful! Sometimes I think we overthink it when trying to get dressed for the rain. I realize some areas get more heavy rain than we do, but you can always wear rain boots on over top of your slim straight ankle jeans, when you need more coverage. Or a waterproof knee boot, such as Blondo.

And, as promised, I rounded up some of my favorite rain-friendly coats below.

Shop My Favorite Rain-Friendly Coats

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