Sneakers have always been my go-to on rainy days, but like an annoying know-it-all, my soggy socks are always there to remind me that sneakers aren’t water repellant. I refuse to let my socks get the better of me anymore! In preparation for late autumn showers, I finally bought a pair of rain boots, or wellingtons if you’re fancy. In a city like New York, where you’re constantly walking from place to place, it’s just down right dumb to continue fighting Mother Nature with inadequate footwear.

And although this story was my idea — I genuinely wanted to know how to wear rain boots and figured the best way to find out was to test them — when boot came to puddle, “wellie style” rendered nothing but a mind block.

I started by choosing a pair of black Hunter boots from their new refined collection. I figured they’d be the most wearable and for styling purposes, I knew I could treat them like a pair of ordinary Chelsea boots. My next step was to choose clothing that would juxtapose the practical utility of a wellington. I understand the appeal of a rainy day sweater, but why not also try dressing up? Spoiler alert: it’s fun! Also, socks. They might be the MVP of this style challenge. Playing around with different colored socks can go a long way when trying to jazz up black rubber boots. Okay, now that that’s out of the way, let’s get down to it:

Rainbow Brite

Hunter boots, Belize striped knit bodysuit, Zara jeans – similar hereGanni bag – similar here

Whenever I’m a little down in the dumps I try to trick my brain by wearing really bright, happy clothing. I apply the same rule when it comes to dressing for gross weather and Mondays in general. Scientific evidence (me) proves it works.

I based this outfit around this really cool striped knit bodysuit from a German brand called Belize. In a sea of multicolor striped knits this season, this color combo takes the cake for me. The jeans are from Zara. I’m pretty sure I wore this exact outfit in Kindergarden and I am not the least bit alarmed by that.

Short Story, Bro

This is my “going mushroom picking in the English countryside” outfit. Do you think Alexa Chung approves?

Anyway, I’m a sucker for Victorian-inspired blouses. I highly recommend adding one to your wardrobe if you’re looking for a new white blouse. They’ll never steer you wrong. I’ve also been trying to facilitate the comeback of Bermuda shorts for the last three years so this is yet another attempt in doing so.

Back to those socks I mentioned earlier: your choice of socks make your choice of shoes look more intentional, like you actually want to wear rain boots with this outfit, not just because it’s raining outside.

Overall Cozy

Since everyone’s ideal outfit for a gloomy day is a big sweater and roomy jeans (or at least mine is), behold the coziest sweater I have ever owned. I found it on Free People and it would be wrong to not tell you about it. I went with overalls instead of jeans to make the outfit more exciting. Not to mention that these are also the best overalls I’ve ever come across (yes I work for Ganni, no this is not a biased claim). When it comes to a rather simple outfit I like to add a statement piece for good measure. In this case, I went for Roxanne Assoulin’s earrings, which I have unofficially dubbed Princess Peach’s earrings.

Sunshine on a Rainy Day

In another effort to combat rainy day blues, opt for a dress that you typically reserve for special occasions. My favorite one, pictured here, is from Ulla Johnson. A marigold velvet dress is a little fancy for my everyday, but if you add a casual jacket it’s just perfect.

Flash Stance

Hunter boots, Zara trench — similar hereGanni Socks — similar hereHayward bag, LoveShackFancy tassel belt — similar here

Last but certainly not least, what’s a rain boot style “how-to” without a trench coat? I can’t think of a better outfit for when you don’t necessarily have anywhere to be, but a lot of errands to get done. If it were colder out I would have probably added a turtleneck to trick you into thinking I’m actually wearing something underneath.

You know what, socks? You were right. I just might start wearing rainboots. (Now what do you wear when it rains?)

Photos by Edith Young.

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  • Adrianna

    ps keeping a spare pair of shoes is pretty life changing

  • Caroline Christianson
  • I just got two pairs of the Bernardo Paige Chelsea rainboots (in black and hunter green), and I soo needed this for some inspo!

    • Juliana Salazar

      I almost went with hunter green ones for this!

  • Sarah

    Never thought about a lot of these combos and typically resorted to wearing leggings when rain books were required – will definitely be trying these looks!

  • Chloe Bruderer

    Every outfit is fire! 😍

  • Pandora Sykes

    KUDOS. You actually pulled off wellies

  • Abby Colby

    Overalls + wellies is IT

  • Esty Turner

    Juliana is my absolute favorite and has the most amazing style

    • Juliana Salazar

      <3 !!! you are too kind I'm blushing!

  • Pham Phuong Le Anh

    Love it

  • Suzan

    Especially love the mushroom picking look and also the marigold dress!! Very awesome ways of dressing up of the rainboots!!

  • Emily

    Except none of these outfits are actually waterproof! Can we please learn how to be chic and also not wet?