Getting dressed for work on a rainy day can add another layer of challenge to your daily outfit decision making process. The unpredictable weather, wet sidewalks, and the need to stay polished can make outfit planning feel a little frustrating. So, I’m sharing a round up of rainy day work outfits and a few tips to help those mornings feel a little easier. First, here are the top essentials I recommend for keeping dry and chic!
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Rainy Day Work Outfits for Different Seasons
Rainy day work outfits are about more than just adding a moisture wicking coat. Your base layer – or the main part of your outfit – is also important. The right pieces will help keep you dry, and also come together so that you look professional without sacrificing your own personal style because of the weather.
Best Fabrics For Rainy Day Work Outfits and Best Shoes
There are a lot of friendly fabrics for rainy day outfits! I don’t really look for so-called water resistant fabrics when it comes to my actual outfit. But, wool and cotton are typically good options when it comes to being naturally water resistant. I also love linen for warm weather because it dries quickly. Shoes are also important. I tend to avoid sandals or other shoes that will let my feet get wet unless I’m just running inside from a parking garage or something similar.
Outfit Ideas: What To Wear To Work On A Rainy Day
Loafers and Tailored Pants for Fall, Winter, and Spring
During the spring, winter, and fall, I love loafers with sock tights or socks for the office. These shoe and sock combinations also work for a rainy day, whether you wear dark jeans or actual work pants. Loafers with a slight heel and sturdy leather tend to do well in rain, but I’d still go for a rain boot for those days when the rain is just non-stop. Click here to shop this outfit.

These jeans are such a good work option because they resemble trousers, but I also included some work pants below that I love.
Cotton Dress For Warm Days
Cotton dresses are a reliable option when it’s warm outside, and there are so many work appropriate cotton dresses or cotton blend dresses. Here in DC, our summer storms are intense and the humidity stays around after the storm. So, things that keep us cool like a cotton dress are important parts of our wardrobe. I’m sure that’s true elsewhere too. These dresses are the perfect base layer to wear alone or build an outfit around.
Some of these dresses would look really chic with a belt, and some of them you can style with a button up underneath for the office. I love how they’re all something you can reach for to wear to work or on the weekend.
When it comes to shoes, I used to always wear my work dress with rain boots and change into my work shoes when I arrived to my desk. This is pretty common to see around DC as a lot of people take the bus or the metro. You don’t have to invest in shoes you only want to wear when it rains – go for a pair of fun rain boots instead and wear the shoes you love when you get to your office.
Fun Polka Dot Skirt
This outfit will look so chic under a trench coat. It’s a classic outfit at its core, but the polka dots make it fun. I just ordered this skirt, and it’s one of those pieces you can wear to work or on the weekend. These slingback shoes are fine to go from your car into an office – your toes are covered and I’ve never found that my feet get soaked if I wear these for a little walk in the rain. If you’re commuting by bus or train in the rain, you’ll want to wear rain boots for your commute. You can also style this with tall boots in the fall!

Linen Skirt or Cotton Skirt with a Cotton Sweater
This cotton sweater and this one (I love the stripes!) are both perfect to style with a linen skirt or cotton skirt on rainy days. This type of outfit works for the spring, summer, and the fall. I love how it feels cozy but you look like you’re dressed for the season instead of winter. You can easily layer with a sleeveless top underneath for added warmth, or in case you get too warm.
Linen Shirt Dress
Speaking of choosing the right fabric, a linen shirt dress is a great example of something that dries quickly. I just ordered this one, and it’s perfect for work. I love how you can take a simple linen shirt dress and add so much to it, whether you want to style it with a belt or just wear fun jewelry. I love to use my own belt instead of the belt that comes with the dress, so I linked several I like.
How to Layer Rainy Day Work Outfits
Rain boots are a good idea
If you have any kind of outdoor commute, whether you walk or you’re catching a bus or train, rain boots are essential. I always wore rain boots when I took the metro to work or when I was commuting in London. Just change your shoes when you arrive at work! This is the easiest solution instead of searching for water resistant shoes for different outfits.
Start with a lightweight base layer that won’t overheat indoors and stick to thin layers to avoid bulk
Cotton and linen are always good options for warm, rainy days. There’s nothing worse than being sweaty and getting rain all over you in the summer when you need to feel fresh for work. So, choose lightweight pieces made up of breathable materials like cotton and linen. The skirts and shirt dresses I mentioned above are a good place to start!
Finish with a water-resistant coat or trench
A trench coat, rain jacket, or water repelling coat is a key layer for rainy days even when it’s warm. Some days you need a hood, and other days a trench coat is just fine!
Keep proportions balanced with fitted or tailored silhouettes
On rainy days, if you choose tailored pants or a slim fitting skirt, you can easily wear a more flowy top to balance out your outfit. I love tailored bottoms for rainy days because they’re less likely to accidentally get wet from the rain.
Okay, I hope this post helps you put together some rainy day outfits that will have you feeling polished and help you stay dry! If you’re looking for other tips on workwear, check out my blog post on casual Friday work outfits. Be sure to sign up for my email list below if you’d like to hear more from me on style and travel.




