I Tried to Tackle My Fashion Achilles’ Heel: Dressing for Rainy Weather

Confession: I’m a fashion editor, and I cannot, for the life of me, get dressed when it’s raining.

I put together outfits FOR A LIVING, but all logic goes out the window and lands with a dismal splash whenever I’m faced with the prospect of clothing myself mid-precipitation. I haven’t felt like myself in a rain-appropriate outfit since I was in Kindergarten and my mom bought me a pair of froggy rain boots and a matching froggy umbrella. When my weather app forecasts dampness, it feels as if I’ve been tasked with creating an ensemble in an alternate reality wherein the grass is up and the sky is down and my brain is made of cotton balls. It’s like I forget how to get dressed and none of my clothes make sense.

In an attempt to administer tough love, I challenged myself to create three outfits for three different kinds of rainy days (light rain, medium rain and heavy rain) that not only felt delightful and fulfilling to wear but also highly practical. I wanted the thought process and resulting ensembles to actually be of service to myself and any other similarly bewildered people, so I carefully broke down exactly what goes through my mind when it’s gross outside and I have to put on clothes:

+Though I normally rely on jewelry to punch up my outfits, I’m not inclined to wear much (or any, really) when it’s raining, because it usually gets covered by coats/hoods/umbrellas.

+I can’t wear anything that brushes too close to the ground (i.e. long pants or dresses).

+Even if it’s not an especially cold day, rain always makes me feel shivery and I regret whenever I wear thin fabrics or not enough insulation.

+I prefer to wear comfortable clothing that’s easy to move around in to better facilitate puddle jumping, navigating around other umbrellas on the sidewalk and general damp schlepping.

+Dark clothing is better in case I get splashed. Also, the more quasi-waterproof or water-friendly materials I’m wearing, the better.

Below are the outfits that ensued and my thinking behind each. If you have any tips and tricks up your raincoat sleeves, meet me in the comments for further discussion.


This outfit is inspired by one Leandra M. Cohen, a unicorn of a human who seemingly does know how to get dressed in the rain — and compellingly, at that — based on this outfit she wore during New York Fashion Week:

An ideal light rain ensemble if I ever saw one! Upon further analysis, I realized that the combination of comfortable but still put-together-looking pants (in this case, the fact that they’re leggings provides the comfort and the slit at the front provides the put-together-looking factor — what is it about a slit that makes pants look so great? Are the fronts of our ankles overlooked territory?) and shoes that are easy to walk in with wooden and thus water-friendly soles is the apex of why it works so well from both a practical and aesthetically pleasant standpoint. I recreated the bottom half of her outfit with clogs from Swedish Hasbeens and a pair of slit-ankle pants from Carbon38 that I actually feel a strong desire to write a whole separate story about because they are such a revelation. Not only do they look great on and feel great on, but they are also MOISTURE-WICKING and thus the perfect wardrobe staple for outdoor drizzle. They’re also on sale for 50% off. This is not an ad I just had no idea how much I would like them until I put them on.

One of the things that annoys me most about getting dressed in the rain is the reality that I’ll probably want to keep my rain coat zipped the whole time outside, which means whatever is underneath will never see the light of day. That’s why, when I spotted this translucent rubber floral Ganni jacket, I knew it was the perfect solution. I paired it with an orange patterned pullover sweater and have never felt more prepared to get spit on by Mother Nature.


Medium rain requires graduating from clogs to rubber ankle boots, which is trickier than it sounds because rubber ankle boots that don’t make me feel like I’m a marine biologist are hard to find. The pair I own currently are a constant source of frustration because they have a strangely wide circumference, making my feet look dorky — and my entire outfit by association. This silhouette appears to be quite a common one when it comes to ankle rain boots, because I had a hard time finding what I was really after: something that looks more similar to a Chelsea boot — that hugs the bottom of my calf — but waterproof. I finally discovered this pair from Kate Spade, which did just the trick (I also really like this pair with a chunkier platform).

From an aesthetic perspective I wanted to show off the boots, so I decided to opt for a skirt instead of pants. I called in this one from Tibi because it’s made of nylon (water-friendly!) and is described as “inspired by outerwear,” which is optimal for inclement weather. I paired it with a windbreaker, which is basically cheating because windbreakers are inherently practical but just so happen to be trendy right now, but I would feel remiss if I didn’t take advantage of this rare and historic opportunity.


Another rain category, another shoe graduation — this time from ankle boots to knee-high. I selected a bright red pair from Hunter for this look because colorful boots are a prime way of injecting intentional style into an outfit that will lean practical by necessity. When it’s pouring rain and I can’t spend the day under a tent, I like to at least try to dress like one. Roomy, comfortable dresses are my go-to, which is why I settled on this one from Tibi. I liked that even though I would be wearing a coat over it, the most interesting part of the dress (i.e. the neon ties at the collar) would still be visible.

In this case, I wanted the coat to perform double duty, not only by protecting me from the elements, but also by being enough of a statement that it could serve as the visual focal point of the outfit. It’s weirdly hard to find a cool, colorful rain coat that isn’t insanely expensive, so my stomach did an internal flip when I first spotted this one from Rains. The only thing it’s missing is a big hood — something I find very useful in my bad-weather outerwear (if anyone knows of a cool, colorful rain coat that isn’t insanely expensive with a big hood, please tell me immediately).

Ultimately, I felt myself (stylistically speaking) and prepared (practically speaking, for the rain) in all three of these outfits, which gave me a crucial confidence boost. I no longer questioned whether I could create rain-appropriate outfits that captured my personal style. Nevertheless, since I knew I would be returning all the clothes that I borrowed for the purpose of this experiment, I made sure to note down important takeaways for my (and hopefully your) future use on rainy days down the road:

+The right footwear is crucial. Invest in a pair of rain boots that you really love and are excited about wearing every time you put them on. Clogs or other wooden-soled shoes are also a viable option if it’s only misting outside.

+A statement rain coat can rescue your entire look. Even if you’re wearing leggings and a sweatshirt underneath, if you have on fun outerwear your outfit is still interesting in a very obvious way. Come to think of it, this takeaway falls perfectly in line with the hypothesis I developed last winter about the power of energetic coats.

+Cropped ankle-slit pants are a great way to circumnavigate normal cropped pant fatigue whilst simultaneously avoiding wet floor-length pant hems.

+You don’t need tons of accessories when you have a good pair of sunglasses.

What am I missing? Tell me below.

Photos by Starling Irving.

Harling Ross

Harling is a writer and was most recently the Brand Director at Man Repeller.

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