Last Updated on September 24, 2023 by Eve Dawes
How to style: Casual to chic cute outfit ideas for rainy days to see you through the greyest days in style
Rainy day outfit ideas can be just as chic as dry days, as long as your hair doesn’t go to hell like mine likes to do as soon as there’s any moisture in the air. Forget anoraks aka rain jackets (although they have their place) for cute rainy day outfits don’t think grey days have to mean drab colors. As I sit here in England in July in the rain, I’m inspired to write this post to cover all seasons, not just the cold ones. There’s a stylish rainy day outfit for all tastes and occasions in this edit from comfortable and casual to smarter looks for work. So keep reading to find the right look for you.
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1. Casual rainy day outfit idea
Loungewear and white sneakers are Ariana Grande and Gigi Hadid cute rainy day outfit go-to’s. Perfect for staying cozy and warm on casual days. Stick to leather sneakers rather than suede and pop up an umbrella to keep dry.
Yes it’s sunny in this pic (I live in Vegas) but you get the idea.
2. Chic rainy day outfit idea
A trench coat with black leggings, a slick bun and knee high boots is an elegant and timeless outfit idea for rainy days that Irina Shayk has done to a fine art. Keep it monochromatic for the most chic way to wear this look.
3. Casual denim rainy day outfit
A denim jean jacket, black leggings or joggers, black tee and sneakers is great for Spring and Fall when it’s not that cold out. Plus it’s comfortable and a denim jacket will always be a wardrobe staple.
4. Stylish rainy day outfit
Leather is a warm and stylish option for creating rainy day outfits with. Don’t limit it to just leather jackets. Leather blazers like this faux croc cream wrap blazer styled with high waist jeans or pants to keep out the breeze works well. Leather leggings, joggers or leather pants also work well. Dua Lipa styles her with and combat boots for an edgy and practical rainy day outfit idea.
5. Blazer, high waist pants and flat ankle boots
If you’re looking for a rainy day outfit idea for work or the office a colorful blazer, high waisted pants / trousers and chic leather ankle boots look polished and adds a pop of color to a grey day. Ankle boots help keep out any drafts.
Pro tip: stick to dark pants/trousers to make any puddle splashes less visible.
6. Cute rainy day outfit
Bella Hadid styled a long sleeve belted dress with loafers which made for a cute rainy day outfit. Add tights or socks which are so in fashion right now for warmth.
7. Faux shearling jacket + faux leather leggings
It doesn’t get much cozier, warmer and more comfortable than a fur shearling jacket and faux leather leggings. It tends to be my go to when I’m in Oregon along with a lot of frizz proof hairspray and a hat.
8 Long blazer dress and knee high boots
For a dressier look go for a longer length blazer or blazer dress and knee high or over the knee boots. For extra warmth add designer tights or leggings. For extra grip go for block heels or chunky soles for a more casual rainy day outfit.
9. Feminine rainy day outfit idea
Sweater dresses and knee high boots are my go to for Fall. Bright colors like this hot pink sweater dress which can also be worn as a sweater with leggings add a vibrant splash to grey days and in my opinion you can never have too much pink in your life. It does come in more colors if this is a little too bright for you.
10. Parisian rainy day outfit idea
Copy Chloë Sevigny’s rainy day style includes flat boots worn under wide leg jeans, a black leather jacket and a beret to protect your hair from the drizzle.
11. Casual leather rainy day outfit
Black joggers are such a versatile piece to have in your closet for creating both casual rainy day outfits with sneakers or adding heels for a dressier look. I always regret it whenever I don’t pack them like I did this Summer! Here’s 11 ways to style leather joggers and all the reasons to have them in your closet.
12. Sophisticated rainy day outfit
As you can tell I have a lot of leather in my closet so of course I had to include leather pants as a rainy day outfit idea. They a look a little dressier than joggers but are just as warm. Copy Jennifer Aniston and style them with a simple black tee, black longline coat, loafers or flat boots for a monochromatic, elongating look. For more of a statement look, style them with a red jacket like I tend to do.
13. Manor born | Countryside rainy day outfit
A Barbour jacket, leggings and flat knee high boots or hunter boots is the quintessential rainy day outfit for the English countryside but don’t save them just for there.
Having been born and raised there, it’s also my go to when I’m home in the Winter. Barbour jackets roll up small for packing but are both wind and waterproof. Flat leather boots are perfect for trekking through the mud and fields.
14. Warm rainy day outfit
How many jackets is too many? Don’t ask. I may live in Vegas but seem to always be adding to my jacket collection. Copy Kendall Jenners casual rainy day outfit in a puffer jacket, loungewear pants or leggings and sneakers.
If you’re traveling go for one like this that folds up small enough to fit in your purse but is still super warm and waterproof. If you’re going to wear white jeans, go for knee high boots to protect from rain splashes and puddles.
15. Sexy rainy day outfit
Trust Jennifer Lopez to put a sexy spin on a rainy-day outfit. Copy her style in a patent leather coat, bare legs and sexy high heel knee high boots.
16. Classic style
A neutral trench coat is a wardrobe staple and looks ever so stylish worn with leather pants and black leather heeled boots on rainy days. Snap this one up for under $100.
Shop the rain day outfits
Some favorite rainy day outfit pieces from leathers to pants to boots, designer to luxe for less:
