I’ve been living in Pittsburgh for the past few months, and though I love being with my family and friends I grew up with, I have a tough time with the incredibly gloomy weather here. Really, seeing the sun in the winter feels like a rare occurrence in the city. It’s also not uncommon for a seven-day forecast to include multiple thunderstorms. But with a pup, staying inside amid a shower isn’t an option. As such, I rely on good-quality rain gear to see me through strolls around the block. But lately, I’ve noticed a lot of my waterproof looks aren’t super stylish — and I’m on a mission to change that before spring rolls around.
The one chic rainy-day look I already own is Hunter’s fire-engine red puffy mules. Since getting my hands on them a month or so ago, I’ve worn them at least once a week for quick dog-walking outings as well as trips to the grocery store. Alongside a khaki trench coat and neutral sweatpants, the shoes are so striking. And though I do have a few practical rain jackets in my collection, I’m on the hunt for something fun and mood-boosting (because dreary weather can really bring me down). Hailing from its Spring/Summer 2025 collection, Prada’s bright, sunny yellow iteration is right up my alley. How could it not put a little pep in my step on a dark, rainy afternoon?
Ahead, I’m breaking down the cute rainy day looks I have my eye on. Might as well face the not-so-pleasant weather in style.
As much as I’d love to style this drawstring jacket atop a flashy sequin dress (as seen above and on the runway), something like a long hoodie and leggings will probably be my go-to.
These olive green clogs from Kassl and Tretorn’s collab are so cool, I’d also wear them on a sunny afternoon with an oversized button-up and relaxed jeans.
After spotting Millie Bobby Brown out in London carrying a leopard print umbrella, I can’t help but want one too now.
This hot pink porcelain toile print feels fresh and unexpected on a rain coat. Plus, it doesn’t need much styling — a tee and casual jeans will do.
Above, my current favorite shoes. They’ve added a burst of color to every winter outfit.
I never knew I needed pastel blue rain boots until now. I’d team these with a colorful jacket — perhaps a vibrant yellow look à la Prada — for some extra punch.
Free People’s poncho can easily be packed up in a small bag, making it a must for upcoming hikes and weekend getaways.
Boasting voluminous sleeves and a funnel neck, WARDROBE.NYC’s anorak is equal parts luxe and functional.
I’m saying goodbye to all my old (and frankly boring) umbrellas for this cheery green style from FARM Rio.
The beauty of these babies are they are elevated enough to sport to the office or for a nice work dinner.