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Writer's pictureWhitney Wisdom

The Art of Dressing in the Rain


April showers bring cute outfits. Cute outfits bring confidence.

Not a hot take but, rain adds drama to our lives. We’ve seen the rom coms, we’ve heard the Taylor Swift songs. And the way I slump into my old for lack of a better word, “waterproof poncho,” hood-n-all is a sight. I would not drop everything and meet me in the pouring rain for a sidewalk smooch in this outfit. Getting dressed, especially on rainy days, into an actual stylish, grown-women-looking outfit, is an art form. By adopting any of these tricks your next rainy day will be cheery instead of dreary.


Umbrellas: So at the very least, we’re talking barebones, order on Amazon level-of-effort. Get a cute umbrella! I think it is no secret, I am fascinated by print mixing. A printed umbrella that color coordinates with your printed rain boots are wise. How often do you wear rain boots when you’re not carrying an umbrella? Ahhh, do you see the light now? When you go to a tiki bar you usually gun for the table with the big bright umbrella. Just think, you could be so lucky to walk under such a happy umbrella as you dodge puddles on the regular. Lots of umbrella’s have screenings of famous paintings. I like the idea of walking beneath Starry Night. One thing is for sure: you are classy enough for that hook handle. Don’t forget it!


There's somethin' 'bout the way the streets look when it's just rained.

Rain Coat & Rain Boot Combos: I don’t hate the classic Salty Fisherman/Paddington the Bear yellow waterproof trench. I actually kind of like it. To wear a bright yellow polyester garment that stretches from your shoulders to your knees is a bold move. With bold moves, comes intimidation, so let’s break it down together. You shouldn’t wear it like an old sea chante or fictional bear (No flipped-up red hats!). Take a preppy bright yellow coat with toggle closure and make it edgy with lace-up rain boots. I am obsessed with Isle Jacobsen’s Rubber Boot because the laces actually make it look like a real, everyday shoe. Typical Hunter rain boots honestly, creep me out. They look like a mold of a foot and calf! Like a cast! They take on absolutely no shape or style on their own and require an outfit that’s heavy on the accessories to kind of hide the functional shoe. Lace-up rain boots actually have soles and the only thing I’m left to debate is: which color do we need more? Tan boots with black laces or olive boots with ivory laces?



The art of dressing in the rain is a merger of trend and functionality. The functional part of selecting rain boots is to really think about when you’re going to wear them. April Showers, ring a bell? Though the fleece-lined rain boots seem fun, be sure to grab a lightweight, non-clunky, pair that works for about 60 degree weather. I always love a floral print but, I especially love it for rain boots - one of the few fashion pieces that are meant to get wet. I love an almost Grandma-looking floral here like lilacs on an ivory ground or clustered dandelions. Pair with a waterproof Trench Coat because what’s the point of Trenches if they can’t handle a little drizzle? Now’s the time to try a mini backpack! Best to have all your essentials on your person as you make a run for it in the rain.



So if the classic route, or the girly route are not paths you take, go masculine. The traditional waterproof hooded quarter zip with the kangaroo pouch can be cool, in you guessed it: olive green. If you take off the sports team logos and get a solid rain coat, you can really see the jacket for what it is: military-inspired. The Packable Anorak jacket by UpWest folds nice and neat. Pro tip: always pack a rain jacket when traveling especially, if you’re planning on spending a good bit of time outdoors. I’d get it in a men’s small or whatever men’s size would cover your butt to make the raincoat cover more ground. AKA a rain dress. Did I just invent the rain dress? Whenever wearing “manly” pieces, I recommend one-upping with a feminine touch like adding your favorite printed tights. Are tights foreign to you? My full article on these leg-hugging gals can be found here.


Yes, you can stand under my umbrella. Thank you for asking.



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