Rainy Day Outfit Tips: How to Stay Dry and Still Look Cute

Hey friends! Today I’m sharing a post that has been highly requested for a good long while now. I finally was able to get some pictures taken on a rainy day because I wanted to show you exactly what I wear when it’s actually raining. 🙂 I’m going to be honest with you guys. These rainy day outfit tips are going to be practical tips that are actually going to keep you warm and dry. Ha! I was looking on Pinterest to see what other people have done on this subject and I was dismayed (that’s way too strong a word, but I’m using it anyway) to see that other people are sharing rainy day outfits that are basically regular outfits with an umbrella. I’m sorry, but if it’s really raining then an umbrella isn’t going to keep your leather shoe safe… even if it is a boot!

No. On a rainy day you need practical pieces that are waterproof and made to withstand the rain and keep you dry. BUT you can still look cute with practical gear! And actually, just this past few months I finally found a pair of rain boots that I really love, and that actually look cute. I’ve had knee high rain boots in the past, but because we drive everywhere (the joys of living in the midwest. ?) the knee high rain boots were always a pain… they just don’t bend the way you need them to! So I’ve been on the hunt for a good pair of ankle length boots, that I would actually want to wear due to their cuteness, and… success!

Karin Emily wears a black rain coat, black leggings, and black rain boots

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Sizing notes: rain jacket – XS (runs big so size down) | leggings – 4 (tts) | rain boots – tts

These rain boots are cute and functional and they are classic so they’ll be my go to pair of rain boots for years to come. I stayed true to size and they still fit chunky socks in them so I’d suggest doing the same.

Okay so let’s break down each layer:

I always like to wear a cozy wool or cashmere turtleneck underneath my rain coat. A scarf has a tendency to get wet, but a turtleneck hugs you close enough that it doesn’t typically get wet, but I like to wear wool or cashmere because even if it does get a bit damp they won’t chafe your skin like cotton would.

I like a plain black rain jacket because it goes with everything. This one is really nice, but on days when it’s really coming down I have an old trench coat style rain coat from REI that’s longer and a little bit warmer. I found something really similar here if that’s something you’re interested in.

I like to do leggings underneath my rain coat just to keep things monochrome, but also because I can tuck them into my socks so I don’t have to worry about my ankles getting wet.

And speaking of socks, I always wear wool socks because they repel water, but they’re also super warm.

Finally, a good pair of rain boots are essential! The combo of the wool socks and waterproof rain boots will keep your feet toasty. I also like how ankle rain boots are more tight around the ankle. With my old knee high rain boots I always found rain dribbling down the inside.

And finally, I like to wear a fanny pack style bag because then I can keep it close to my body under the umbrella (I can even zip it under my rain coat if I want to!). I don’t like to bring out my leather purses when it’s raining.

So there you have it! Those are my practical tips for dressing for rainy weather. I hope that helps anyone who had questions!

That’s all I’ve got for you guys today. I hope you have the best week!

Until next time,


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