Outfits for Cold and Rainy Days

Dressing for the rain… okay. Dressing for the cold… okay. Dressing for rainy and cold… not so okay. I feel like it’s nearly impossible to look cute when you’re trying to stay warm and dry. (Getting out of bed on cold and rainy days is a challenge in and of itself.)
When the weather is not cooperating, I half want to just wear jeans and a fleece and maybe not leave my apartment ever. But, while rainy days aren’t exactly beautiful, there are some fun things about it and being cooped up in an apartment all day means you’ll never experience them.
Casual Outfit | When you have the luxury to dress a little bit more casually, thick sweaters and jeans are the way to go. I like to opt for a little bit of color in the sweater… and who could resist those red Hunters? This outfit is perfect for running around town and popping in and out of stores.
A smidge dressier | Skirts with thick tights are the way to go. Bean boots are cute too and they totally keep feet dry for all the puddles. I also really like quilted vests plus crisp button downs. Super perfect for autumn days… that are a bit overcast.
Staying in bed | And if you can’t quite get out of bed, don’t worry… I won’t judge! Snuggle up in your warmest sweater and flannel pajamas. And if you absolutely have to get out of bed (for, like, a cup of coffee or something)… you better have insanely warm slippers on.
What are you cold and rainy go-to outfits?

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I've been eyeing that first sweater since my J.Crew catalogue came, it's so cute!

xx Emily @


These outfits are all perfect for cold days! We're expecting snow this week so you can bet I'll be wearing my favorite sweater and coziest pajama pants!



Yay! This post is like the epitome of England! I'm constantly getting stuck in the rain without my unbrella, ughhh! Hopefully I can pull together an outfit for cold and rainy days.


I have a North Face rain jacket that is lined with a really soft fleece, so it's perfect for rainy days that are also a bit chilly!


I love your outfit choices! Usually on cold and lazy days I whip out my yoga pants and a t shirt and a my favorite sweat shirt! You have so many great things going on in your life! Congrats! You truly are an inspiration.

lillies & lattes

i adore the style advice! (i wore my hunter boots today in honor of your post.)

where did you find the grey skirt? it's perfect for teaching in cooler weather. (i can't seem to get the link to work)


Thanks for the recommendation! I wore the second one today to a committee meeting! Super cute, and oddly professional despite the rain. Thanks!


Great outfits, but the link for the grey skirt does not work. Would love to check it out. Post the correct link, please? Thanks so much 🙂

Julia D.

Sweaters. Bean boots. Thick socks. Sometimes when its really cold I'll even wear thick tights UNDER my jeans for extra warmth.