If you’re anything like me and the weather can be bipolar, you know the importance of being prepared for those unpredictable days. So on those grey, drizzly afternoons where all I want to do is stay inside and drink hot chocolate, I reach for my rain boots and winter coat.
Though a pair of rain boots is perfect for that trek from your car to your office (and vice versa), a work outfit with a little more color could be just what you need when the sky starts to pour. This list has some of my favorite work outfits appropriate in any season or weather condition.
The work outfit I have pictured above is my favorite rainy day work outfit. I love the color of the rain boots, and they go so well with this navy blue skirt and light lavender blouse. The skirt has a nice flare, which makes it appropriate for business, and the color can easily be matched with any blouse or top you have in your closet.

Table of Contents
- 1. Cozy, Warm Layers
- 2. Long Jersey Sweater & Heeled Boots
- 3. Man Repeller
- 4. Barefoot Blonde
- 5. Long Coat On Chilly Winter Days
- 6. Waterproof Style
- 7. Styling Red Rain Boots
- 8. The Minimalist Outfit
- 9. Patterns And Denim
- 10. Brown Boots and Bag
- 11. Leopard Pants
- 12. Classy Coat Style
- 13. Black And White With Long Boots
- 14. Washed Blue Anorak
- 15. Marilyn Plaid Trench Coat
- 16. Raincheck Packable Raincoat
- 17. Winter Or Fall Work Outfit For Rainy Day
- 18. Classy In Plaid
- 19. Cutest Rainy Day Look For Office
- 20. Rainy Day Outfit With Long Coat
- 21. Fall Day Work Attire
- 22. Cold And Wet Day Outfit
- 23. Hot And Wet Day Look
- 24. Rain In Fall and Hunter Boots
- 25. High Waisted Crop Jean
- 26. Vinyl Crop Smock Colorblocked Raincoat
- 27. Colby Cropped Vegan Leather Bomber
- 28. Storm Seeker Batwing Jacket
1. Cozy, Warm Layers
This simple but charming style can make getting dressed a breeze on a wet morning. For added warmth, layer your sweaters and add a vest. This is ideal for those frigid days when all you want to do is stay in bed! Don’t field calls, and keep your head buried in your pillow. Your body will thank you later! Also, do not forget to slip on a pair of cute rain boots.
Even if they look a little out of place, they are ideal for dealing with drippy and sometimes muddy streets. If you want to be a little more dressed up, try pairing those boots with a dressy rain jacket or an umbrella cover. The cape is quite in style this season! If you prefer not to wear tights, these boots are for you! They are waterproof, which means that your socks will stay dry even if the rain puddle is deep enough for swimming.
2. Long Jersey Sweater & Heeled Boots
In the rain, high-heeled boots come in handy. They’ll not only keep your feet dry, but they’ll also keep you warm! Wear it over leggings and a long, beautiful blue sweater for a warm, elegant outfit that will have you looking forward to wet days at work. I recently gave a similar look, with a different pair of brown boots that I wore with a brown v-neck sweater. And on days like this, leggings are perfect! I got my leggings at Kohls’s, and I like the ones I have because they’re not too thick or tight. That way, you can layer them under pants for extra warmth.
3. Man Repeller
An all-white ensemble capped with a classic trench is a timeless outfit. Choose loafers that a few drops of rain won’t destroy on rainy days. Also, take a look at these Women’s Trench Coat Outfits. Luxury is another word for crafting the perfect outfit for every season. If you want to feel luxurious, you have to know how to create an atmospheric outfit.
4. Barefoot Blonde
Wear a knee-high black boot with a tiny black dress. To protect your clothes from the weather, finish it off with a coat that covers the majority of them. Layer over a lightweight pullover with a fur collar and sleeves. Then throw on an oversized red scarf to maintain your current no-nonsense look.
5. Long Coat On Chilly Winter Days
Warm up your attire with a pair of tights if you wear a skirt and top. Wear a pair of chunky heel heels to work that is rain and office-friendly. This winter, there are 20 different ways to wear long coats. Whether you’re pairing it with a non-matching skirt, changing up the length, or wearing layers, it’s all about making the best use of your favorite coat. However, if you’re wearing a wrinkled piece to work, smooth it out by hanging it in your room instead of tossing it on a hanger.
6. Waterproof Style
If you don’t mind wearing gumboots to work, you’re ready to take on the day! This type of footwear is popular right now since you may choose from various colors and prints (including bright yellow and pink) to make it lively and pleasant. Wearing those fantastic boots, an oversized scarf, and a fashionable leather cover-up or coat might make for a tremendous rainy-day look.
A great addition to this ensemble is a feminine shoulder bag. Make sure it’s a style that peeks out from the coat or over a shoulder. Not only will you stylishly be able to carry your stuff around, but at the same time, you’re not going to lose your goodies in the process. As a last resort, if all else fails, you could always try wearing a cute raincoat or umbrella!
7. Styling Red Rain Boots
You’re ready to rock the party if you don’t mind wearing gumboots! This type of footwear is popular right now since you may choose from various colors and prints (including bright yellow and pink) to make it lively and pleasant. Wear those nice boots, a bright umbrella, and a fashionable leather cover-up or coat to put together a rainy-day look. Add a touch of color and originality with a pair of skinny jeans, a long-sleeved white top, and a leather jacket. A belt will complement your destination outfit.
8. The Minimalist Outfit
Fitted jeans with a hemmed ankle and short booties are among our favorite rainy-day outfits, especially for those light drizzling days. Pair them with a t-shirt or crewneck sweater, and you’re ready to go.
9. Patterns And Denim
A patterned dress paired with a denim jacket and chunky ankle boots is always a lovely rainy day ensemble. Unfortunately, it’s been cloudy, dreary, and perfect for feeling the gloomy mood in your bones. Luckily, you can use plenty of patterns to create a chic look like this one. If flowers are more your style, then go for a floral pattern, or if you’re feeling inspired by traditional designs, choose geometric prints. Either way, it’s essential that whatever flower you pick is compatible with denim (and vice versa).
Putting together an outfit for these wet days has never been easier! Not only do these patterns give off an edgy vibe, but they also work wonderfully with almost any color.
10. Brown Boots and Bag
You can construct this unique combo if you prefer earth tones. Get your brown boots and a huge handbag that is a couple of shades lighter. You can wear olive green and any shade of blue with this outfit. Play around with the colors and see what you can come up with.
11. Leopard Pants
Animal patterns are enjoyable to wear and are always an intelligent choice when correctly combined. Choose cherry-colored high heels, an orange-colored handbag, a blue shirt with white designs, and a cream coat. The sky and the road are blue these days, so you can also wear a sky- or road-colored cardigan.
Dainty shoes, beige and grey high heels, an autumn kit, a red skirt with cream flowers, or a dingy sweater with black items are all interpretations that won’t look out of place in this outfit.
12. Classy Coat Style
Choose this exquisite cream and black coat, light blue jeans, brown rain boots, black hand gloves, and this cute black and white dotty umbrella if you want to appear classy.
For specific office jobs, the chances are that you’ll need to wear an outfit that is both work-appropriate and also matches the weather. And while this might sound like a difficult task, thanks to the wide selection of clothes available for all types of people, there’s no need to panic.
13. Black And White With Long Boots
Wear a black boot with a white dress. A black bag completes the appearance on a wet day. On a rainy day, you might want to dress up and wear these black boots with a white dress. A black bag is also an easy way to complete the outfit when it’s wet outside. It’s a casual look for today.
14. Washed Blue Anorak
A long, functional anorak in a pastel tint will help you beat the elements. There are enough pockets to hold all of your belongings and cinch pulls to keep you safe from the weather. Any storm can be weathered with a soft henley, white pants, and a combat boot. Embrace the rain and the overalls.
15. Marilyn Plaid Trench Coat
This plaid, belted trench coat features a classic print that looks brand new. It offers just the proper masculine vibe while remaining feminine. Put on a leopard print outfit to create a print contrast. The neutral colors of the coat lean on the side of black and cream. The collar flaunts a pattern that is so distinct that it helps to fulfill the purpose of a nameplate. The coat has pockets for hands-free storage.
16. Raincheck Packable Raincoat
This raincoat is not only cute and functional on a rainy day, but it also folds up into a cute fanny pack. Put it in your luggage for a fast change or wear it as a fanny pack when out and about to avoid being caught in the rain. Fits nicely in your pocket or purse too. It is also a great gift idea for a grumpy boss or teacher.
17. Winter Or Fall Work Outfit For Rainy Day
The umbrellas are the only thing missing from these ensembles. Both designs feature a pant that stops right at the ankle, preventing you from dragging damp hems. Both of these shoes are excellent rainy-day options. Boots with rubber soles help you keep your footing (or at least stay upright long enough to get to the next dry spot). Mary Janes are an excellent option if you’re on your feet most of the day. If possible, bring a sweater.
18. Classy In Plaid
This adorable outfit would be great to wear on a rainy day. The shirt and pants are available in numerous colors, but I went with the red plaid for this post. This is a great outfit that can be worn to school, work, or even running errands. You could even switch out the red plaid for a different color if you wanted something more versatile. It’s simple, yet cute and the plaid pattern is not too busy. I am wearing size xs in the shirt and 24 in the pants.
19. Cutest Rainy Day Look For Office
The umbrellas are the only thing missing from these looks. In both appearances, the pant terminates right at the ankle, preventing you from dragging damp hems. These two shoes are excellent rainy-day options.
The cut of these pencil skirts goes with the natural line of the legs, making it a flattering choice. The one on the left looks like it would be a good option for walking in the rain. The sleeves and neckline also look like they would keep you dry.
20. Rainy Day Outfit With Long Coat
There’s no better way to embrace the rain than to spend a day with a friend or loved one and made a new memory together. This Rainy Day Outfit with Long Coat from Target has everything you need for that chilly day out. Layer this over your clothes for the perfect comfort and warmth under those droplets of water. It is also so stylish, and it can be worn on its own without any other outfit being needed.
You can wear it as a regular jacket and pair it with a T-shirt or sweater. The long sleeves and bottom part can be tied up to create a unique style. This jacket is waterproof, breathable, windproof, and has temperature control. The inside of the coat has a lining and pockets for your items. The backside of the coat also has zippers, so you can quickly get in and out of this garment. This raincoat is made of stain-resistant materials that help in repelling water droplets from getting through, and so it keeps you dry even if you are walking around in the rain for hours.
21. Fall Day Work Attire
For wet days, flat ankle booties are a great option. They are lightweight and can be worn once you arrive at your location. You can wear them with a leather skirt or grunge fitted pencil skirt.
A classic shirt dress is another excellent option, but you can tone down the vibes with a t-shirt underneath and black jeans. A cardi will keep you warm, and it’s will be easy to throw on when you’re done working. For days that are too chilly for your shirt dress, keep your look chic and classy with a blazer! A blazer works exceptionally well with pants or simple dresses. Stay warm in this fall weather for less than $60! The entire outfit would cost about $130 if bought separately, which is quite an affordable price tag.
22. Cold And Wet Day Outfit
A rainy day work outfit should include a poncho or umbrella to protect yourself from the rain. When it’s raining, it’s not only the weather that makes you cold and wet but also your clothes. To combat this, you can wear a raincoat or rain jacket over whatever you’re wearing to protect your clothing from getting wet. The main point here is to try and stay dry no matter how long it takes to get home.
If your look requires you to stand outside in the rain, don’t forget waterproof footwear! Of course, boots are always a good idea, but if you don’t have them handy, opt for a pair of thick socks and rubber shoes instead.
23. Hot And Wet Day Look
No one wants to work on a wet and cold day, but you could always go out in the rain dressed appropriately. Even if it’s not pouring outside, wearing a light water-resistant coat is advised. You’ll want to wear layers if the temperature is chilly. Make sure you have an umbrella with you and that your shoes are waterproof and comfortable for walking in wet weather, no matter what type of climate you live in!
24. Rain In Fall and Hunter Boots
Rain is a treasured commodity in Fall, but we see increased rain. I know what you’re thinking. Therefore, there’s no need for an umbrella or to carry an additional coat just in case. However, the truth is that your actual “rainy day” attire is only about one thing: Hunter Boots!
Hunter boots are waterproof and breathe exceptionally well (although they can still get uncomfortably soggy after a few hours). As a bonus, they keep your feet warm (or are easier to stay on while wet) in cold weather. However, wearing traditional shoes or boots with stockings can be uncomfortable when it rains at night or even during the day.
25. High Waisted Crop Jean
A polka-dot top will add some fun to your rainy day’s fit. Wide-leg cropped jeans go well with them, and black ankle boots will keep you dry in the rain.
A striped polka-dot top with high-waisted, cropped jeans is the perfect outfit for any rainy day. Just pair it with black ankle boots to stay dry during the rain.
When it seems like no matter what you do, your outfits are soaked by the time you’ve made it to your car after work, turn to this high-waisted crop denim look with black ankle boots. The crop pants will keep your legs warm and dry, while the crop top hides any wetness that may have crept up on you earlier in the day. Just be sure that both pieces are fitted enough to avoid getting too drenched.
26. Vinyl Crop Smock Colorblocked Raincoat
If it’s only lightly raining outside and the weather says it’ll clear up later, go ahead and do it! Under a transparent vinyl raincoat, a white tank and trousers will look fantastic. If it’s raining cats and dogs outside, wear a rain hat and bring along a plastic coat.
27. Colby Cropped Vegan Leather Bomber
On the outside, this gleaming bomber jacket will keep you dry, but the quilted inner will keep you warm on the inside. The hunter-green color looks well with white and cream tones, and thick-soled sneakers will keep your feet dry.
28. Storm Seeker Batwing Jacket
A navy camo-printed jacket with a hood and belted waist is practical and fashionable. Combine it with black leggings and sneakers (or rainboots!) for a sporty look on gloomy days.