Rainy Day Outfits for 2024 (No Rain Boots Required)

I don’t know about where you live, but we get a lot of rain here in Philly, especially in the spring and fall. It’s tempting to give up on style when you’re dressing for a rainy day, but all that does is sink you further into the muck and the mire.

Rainy days are depressing enough without feeling like a schlump on top of it, so today I rounded up a bunch of practical yet stylish rainy day outfits for your wardrobe-planning inspiration… no rain boots required!

The key to feeling stylish and put together on a rainy day is to have rain-friendly clothing that is current and aligns with your personal style goals – most importantly, shoes and outerwear. Ever since I’ve been more intentional about putting pieces into my wardrobe that can accommodate rainy weather, it’s been much easier to get dressed on rainy days and still feel good about how I present myself to the world.

So without further ado, here are 10 of my favorite rainy day outfits for this fall/winter season.

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

Stay In Touch

If you liked this post, be sure you’re signed up for my email newsletter. In addition to my most recent blog posts, you’ll receive exclusive newsletter content like special sales, my newest favorite finds, and an occasional peek behind the scenes — all delivered right to your inbox.

I would also love for you to join my JLS Fashion Insiders Facebook Group! This is a friendly place to discuss all matters of fashion and style with other women, share your outfits, get advice, and stay up to date on all the happenings in our community.

This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!

Join the Conversation

20 thoughts on “Rainy Day Outfits for 2024 (No Rain Boots Required)

  1. Your prior post on rainy day style was one of my favorites of the past few months. I’ve returned to it a number of times and bought a bunch of items from the post, like the Steve Madden Chelsea boots (which are just such a great flat casual option even when it’s not raining.) This one is super helpful too. I have that puffer in two colors plus the Treasure and Bond leather bomber, and this opens my mind to thinking I could wear those on some rainy days instead of a more traditional rain jacket. Apparently NYC has more total rainfall per year than London… that’s my excuse for investing in this stuff, ha!

  2. I realized several years ago that I didn’t have rainwear, which is ridiculous because I live in Ohio and we get a lot of rain. So now I have a casual rain jacket and a navy raincoat, sort of like a trench. Plus, I do have short red rain boots, and knee-high black/white ones for when I want to have fun with my outfit. Also, I wear running shoes with my scrubs for work, so the rain boots come in handy so I won’t get my work shoes wet.

    Of course, looking at this post makes me want another rain jacket/coat. Hmmmm….

  3. I appreciate the encouragement to not give up just because it’s raining outside. I sometimes give up, but I agree it affects my attitude. Thank you for showing examples. I will be changing my attitude right now!

  4. I’ve been eyeing the Gap sweater. It looks so low cut on the Gap website. It looks great on you. Did you have to size down in order to get that fit?

  5. Such a great and relevant post! I moved several years ago to MA from sunny Los Angeles and had to rethink my entire wardrobe. I discovered Blondo and Aquatalia for booties and boots, durable leather purses and Longchamp vinyl purses, and a hooded raincoat. I recently purchased a Helly Hanson raincoat in traditional yellow and love it. Thanks!

    1. Yes, it’s definitely a different climate over here! I went from VA to MA for college, and I couldn’t figure out why I was always cold, until a friend gently suggested I get a winter coat. Haha! Made all the difference.

  6. This post is timely as I live in the PNW where it rains pretty much from Fall thru Spring. I did recently purchase a pair of Blondo Waterproof boots but for other boots I spray them with Waterproof spray every Fall. On your Paige Laurel Canyon flares, do you press the crease in them after washing them? I washed mine before hemming and the crease came out…

    1. I lay mine flat and put the seams together and take my hand along them to creat a slight crease while still damp, then hang them up by the bottom hem so they remain creased. I hope that makes sense.

  7. The neckline on the Jenni Kayne sweater you linked looks so much wider on the model almost a boatneck. Is the quality of Jenni Kayne worth the price? Thanks!

  8. Great post! Regarding the Jenni Kayne sweater: I’m thinking of purchasing since the sale has started. Trying to decide between the everyday sweater or the fisherman’s knit. Do they both have a similar fit? If you were only going to have one- which would you recommend purchasing?

    1. The fisherman is much nicer; it is 100% cashmere. I also prefer the fit, as it’s a little shorter. I love the fisherman – definitely one of my top 5 favorites sweaters. Probably top 3.

  9. This is a timely post as I live in the PNW where it rains pretty much from Fall to Spring. I recently purchased a pair of Blondo Waterproof boots and for some of my other boots I spray them with Waterproof spray each Fall. On your Paige Laurel Canyon Flares did you press the crease in again after washing? I washed mine before hemming them and the crease came out in the wash…. Trying to decide if I want to crease them every time I wash.

Want More?

Jo-Lynne Shane on Instagram

Click an image below.

Follow @jolynneshane