Rainy Day Outfit Ideas
I don’t know what the weather has been like where you live, but here in Houston, Texas, it has been raining non-stop for the past two weeks. And while I’m definitely not complaining—we desperately needed the rain after a completely dry summer (seriously, not a single drop!)—the constant drizzle had me thinking: it’s the perfect time to share some rainy day outfit ideas!
As a Houston wardrobe consultant and personal stylist, I know firsthand how tricky it can be to look cute and pulled together when it’s pouring outside. So today, I’m breaking down a few do’s and don’ts to help you stay chic, casual, and comfy in your rainy day gear—no matter the season.
You’ll find both spring/summer and fall/winter personal styling inspiration below, featuring rain boots, hats (because hello—frizz), trench coats, and more. Not into traditional rain boots? No worries—you can totally opt for dark boots or durable shoes instead. Just make sure to skip the open-toe sandals and fancy footwear. We want fashion and function here—because nothing ruins a good outfit like soggy socks… or worse, slipping and spraining an ankle. 😅
A few things to keep in mind when dressing for rainy weather:
✔ Stick with durable, water-friendly fabrics.
✔ A good-quality parka or trench coat is worth its weight in gold.
✔ You don’t need multiple raincoats—just find one that works with your existing wardrobe and offers a strong cost per wear.
As someone who offers virtual wardrobe makeovers and personal shopping services, I always encourage my clients to work with what they already have. A little creative styling goes a long way! And remember, accessories like hats and rain boots can totally transform your outfit—even if you’re just running errands or grabbing a quick coffee.
SUMMER LOOKS
Outfit details: Dress // Boots // Necklace
About this look: Keep it casual with a chambray dress and rain boots! It's light and easy! For this outfit, I also added a bodysuit underneath the dress for an elevated look.
Outfit details: Dress (same brand, similar dresses here!) // Boots // bandana (Similar)
About this look: I LOVE this dress, I found it earlier this year for rodeo, and I love how it looks with these rain boots. The length is perfect too with these boots
TIP #1
Don't: wear light-colored clothes, like white pants or white sneakers.
You don't want mud and debris on your shoes or pants!
Do: wear dark-colored clothes and water-resistant rain boots!
Outfit details: Jacket // Top // Shorts // Boots // Necklace
About this look: This is something I would wear if I have all the kids with me. I can toss on this thin jacket if I need to cover myself from the rain or take it off if it gets too hot.
Outfit details: Top // Pants // Boots // Necklace
About this look: Just a simple graphic tee, and skinny jeans! I would only recommend skinny jeans or cropped jeans. I mistakenly wore my flared denim just last week and got caught in the rain, and it was a MESS. My 90's came rushing back with soaked jeans. IYKKYK.
Outfit details: Dress // Boots // Hat // Necklace
About this look: Another dress, only because it's possibly the easiest to wear in the rain, and in the summer.
TIP #2
Don't: wear wide-leg trousers.
Do: opt for skinny or cropped pants where they retain the shape,
and you don't have to be sorry about the hem of your jeans getting wet.
Outfit details: Top // Skirt // Belt // Boots
About this look: If you don't want to do a dress or jeans, try a slip skirt instead. Paired it with a graphic tee, and a belt to elevate the look, but again these Chelsea boots are great to have for the winter snow or summer rain!
WINTER LOOKS
Outfit details: top / jacket / jeans / boots
About this look: This is a classic look in my book. You can easily swap out a top like this for a graphic tee, or a button-up, and it's still chic and a great go-to look when raining. You can also swap out the boots for whichever one you like too! P.S. I love the green, black and white color combo ?!
Outfit details: top / jacket / shorts / stockings / boots
About this look: I ADORE this look. Same principle here, if you don't like stockings, you can also wear shorts with a top and your rain boots. I love stockings during the fall/winter for an extra layer to keep warm! They also add such an exciting element to the outfit!
Outfit details: dress (similar) / jacket / boots / stockings / hat
About this look: I also love this look. I love mixing florals and edgy pieces! This outfit with the stockings is another favorite! What do you think of this rainy day outfit? Don't forget your accessories- a felt hat is a good way to keep hair and make intact ?
TIP #3
Don't: wear fabrics like silk (hello water stains).
Do: wear simple fabrics.
Outfit details: sweater / jacket / pants / boots
About this look: A simple and chic look, leather is a huge trend in 21/22, and this is a fun way to incorporate that even into a rainy day outfit! To keep the outfit simple, I added an oversized sweater!
Outfit details: top / jacket / pants / boots
About this look: Casual and comfy! Sweat sets are still a hit, and I don't blame the craze. Just add a trench coat or parka and your rain boots!
Outfit details: top / denim / boots / jacket
About this look: A basic bodysuit and denim, but make it rain-ready chic. You can swap out the boots if you would like and or a jacket.
TIP #4
Don't: forget your accessories
Do: wear a hat, or grab your umbrella to keep your hair and makeup intact!
Outfit details: top / jacket / jeans / boots
About this look: This is just like the first look, but I wanted to share how the different jackets and boots would look visually! I'm a visual girl, so I figured all my visual girls would like to see too!
TIP #5
Don't: forget your coat
Do: make sure it is indeed water repellent.
Outfit details: top / jacket / skirt / boots
About this look: Similar to the first look, but with more of a feminine vibe thanks to the skirt. I would just pay attention to the length of your slip skirt, and the height of your boot shaft. You want to avoid the boots being too bulky or too high, and you want to prevent the length of your skirt from cutting off your legs and making you look shorter.
You'll have to comment down below, what rainy day look is your favorite? I would love to hear from you!
SEE SIMILAR POSTS HERE:
BYOW: HOW TO WEAR YOUR SUMMER DRESSES IN THE FALL
