Rainy Day Outfit Ideas For Spring: 6 Tips & Tricks
I’m experiencing my first spring in our new hometown and It. Is. Picturesque. It’s like springtime straight out of a storybook. And it’s the reason I’ve become obsessed with spring fashion.
With a good storybook spring comes some glorious rainy days. I’m someone who prefers buying less and getting the most wear out of my pieces, so my rainy day outfit ideas come down to a few key (& simple!) pieces.
matching set (L) | striped version | boots
For me, a good spring wardrobe consists of the perfect combination of shorts and sweaters, easy matching sets, coats that can get wet, and a good pair of rain boots.
6 Rainy Day Outfit Ideas For Spring
I think getting dressed for a rainy spring day is the most fun when it’s easy.
The ethereal-garden-farmhouse pinterest aesthetic is dreamy, don’t get me wrong, but I often get stuck trying to make something so grand that I lose the practicality of it. And a rainy day requires at least a little bit of practicality (aaaand so does mom life).
These 6 outfit ideas help keep the necessary ease to my outfits that I like while still allowing me to, you know, enjoy my outfit!
#1: Invest In A Good Boot
I have been getting some serious wear out of my favorite rainboots (and LOVING how outfits look in them!).
I was super tempted to go with a bold color or even a lighter neutral rainboot, but in the end, I’m glad I stuck with a classic black. These boots go with everything. And I especially love the matte quality to them, which feels a bit more modern + elevated than a glossy pair.
While rainboots are easiest to pull on with shorts, the weather isn’t always that warm. So I’ve simply grown accustomed to that youthful baggy-jeans-stuffed-into-boots look. But if that’s not for you, just rotate your slimmer pants into rotation this spring (as I do down in outfit #6).
#2: Have A Few Matching Sets On Hand
I swear by matching sets for anyone who wants a cute outfit with as little fuss as possible. This can be a workout set (seen next), a linen set, or one of my faves for transitional weather, a sweater set.
matching set (L) | striped version | boots
This long sleeve top x shorts combo is my favorite. It’s my dream combination of being covered, comfy, yet still breezy. The shorts are an easy pairing to tall rain boots, and the light, loose knit of this one is amazing for warmer weather.
This set also comes in amazingly cute striped versions, too!
matching set (L) | striped version | boots
#3: Layer Your Rain Jacket
If you don’t have a rain jacket, honestly, I get it. I’m not often outside for long periods of time when it’s raining, and a trench coat can work just fine going to and from a building and car. Any outfit in this article looks just as cute (if not better??) when swapping the rain jacket for your fave trench of any length.
jacket (L) | hoodie (XL) | leggings (M) | sports bra (L) | sneakers
But for those of us who have a rain jacket and appreciate a little help in making it look, uhm, less rain jacket-y? Layer it with a cute hoodie!
This zippered hoodie doesn’t break the bank, plus it has longer sleeves that can roll up under jacket sleeves. It’s also super lightweight, so it doesn’t add a lot of extra heat on warmer rain days.
jacket (L) | hoodie (XL) | leggings (M) | sports bra (L) | sneakers
PS – they make my rain jacket in a longer length, too!
#4: Lean Into Longer Shorts & Rainboots
‘Tis the season for longer shorts. These are on trend, but really nice for a rainy spring.
sweater (L) | tee (M) | shorts (28) | boots
Longer shorts still provide the easy pairing to longer rain boots, but with the greater leg coverage they have, it’s also really nice on a cooler day. To feel more modern in a longer short (and less skater girl!!) I lean into light, neutral colors. It’s easier to feel chic when the outfit is giving coastal vibes!
sweater (L) | tee (M) | shorts (28) | boots
A big question I get lately is about these shorts, mostly due to the fact that my frayed white wash with the cool drawstring sold out immediately and they replaced it with…another white pair without those cool details. But both Gap and COH have extremely similar versions (with the drawstring!) I would suggest checking out.
#5: Wide Leg Linen Pants Create for Easy Boot Pairings
Something I recently discovered is the beauty of a wide leg linen pants ease of pairing with rain boots, simply because they can hang out as easily over the boots as they can be stuffed down inside.
sweater (L) | pants (M) | boots
The lightweight, thin quality of linen not only allows for this either in-or-out styling with boots, but it also makes it comfortable to wear over a tall rainboot. Jeans and any thicker, more stiff pant can feel awkward over a tall boot. Not to mention, you see a lumpy boot awkwardly sitting underneath.
Light linen flows easily around the boot, doesn’t get caught on it, and doesn’t look awkward.

sweater (L) | pants (M) | boots
At the time of writing this, there’s trickling sizes of my linen pants left at Anthropologie and even at Backcountry but they go fast. While you can pre-order the pistachio color at Revolve, I found a super similar linen pant you can grab right now!
#6: When In Doubt, Keep It Classic
That good ol’ 90’s straight jean + belt into a tall boot is a classic for a reason. It always works.
jeans (28) | similar tank | sweater (L) | boots
I threw this on the other day when headed to a casual event and really wanted to feel cute but had zero brain space left for putting together an outfit. It was incredibly rainy so rainboots were my automatic go-to, and I simply reached for all the classic items. The look gives 90s minimalism, a little equestrian preppy, and a whole lot of timeless.
Happy rainy days!
Amy
Let’s be friends on Instagram or come hang with me over on TikTok: Sharing life with my husband + kid, daily style & beauty faves, and never-ending Taylor Swift dance-athons…all with a good dose of relatable mom nonsense, too.










