Style Session |

Key Pieces for Moving into the Cold + Rainy Season (With Style)

In case you’re new around here, let me tell you a little bit about where I live. Home, where I hang my hat if you will, is the beautiful Pacific Northwest, specifically Portland. My family moved to Oregon when I was in the 6th grade, so at this point, I consider myself an Oregonian. Most of my extended family lives here. And my maternal grandparents moved to the state about two decades before my family did. I grew up in Eugene (go Ducks!) but I moved with my family (aka spouse and three kids) to Portland almost seven years ago. But those are all background details of this story in which the main character is: the weather.

In western Oregon (where all the biggest cities are) the rain starts in October and it continues straight through to March, April, May, and June. Though it becomes more intermittent in those latter months. In case you’re not counting, that is 6 months of rain per year PLUS. Naturally, much of my wardrobe is built around rain. However, I am *not* one to don technical gear or rubber rain boots… unless we are having a serious downpour. The rest of the days I’ve learned to adapt my everyday style to function in the wet and drizzly weather.

Since we were home most of last fall – aka not taking kids to school or going places – this fall what to wear is more top of mind than usual. I’ve been mulling over which are my favorite types of items – the ones that make life functional (and stylish!) in this season, and I am sharing them below!

1. Coat With Hood

The importance of this one cannot be overstated. When you’re walking and holding hands with multiple offspring, there are no hands to hold the umbrella. Nor when you’ve got a cart full of groceries in the parking lot, or when you’re headed out of Target with all your hands full of small purchases because you refuse to add yet another reusable bag to your collection (that you forgot to bring in the first place). I LIVE in my hooded coats, especially in the fall and spring.

My requirement for a hooded jacket is that it must be rain resistant. I don’t need ‘waterproof’ for most days because I am popping in and out of the weather, not standing in it for hours on end. This goes back to the technical aspect. If I were attending a soccer game or trying to get around in a downpour, I might go for something more waterproof. But for most days, I want something that easily sheds light rain and keeps me feeling like my style-minded self.

I use an old Everlane Anorak, and I am quite fond of it. It has a loose fit and can easily be layered over most of my sweaters. Mine is an old black one with straight hems, but now they feature shirttail hems and beautiful colors. I like the bay leaf and two-toned taupe. I am thinking about trying out a rain jacket by the aptly-named brand RAINS. They make that beautiful green one featured in the opening collage as well as the belted one linked above.

2. Half-Zip Sweater (or Sweatshirt)

I sang the praises of this style on Instagram the other day, and I feel like it’s worth repeating here. I know this style is super trendy, but hear me out. It’s also highly functional. The zipper is really handy for widening the neckline for taking the sweater/sweatshirt on or off. I don’t know about you, but I hate smearing my face on the inside of a sweater (bye-bye makeup) or smashing my hair down after it’s freshly styled. This neckline solves that problem, AND it looks super cool totally zipped up (especially under a jacket) AND it looks super cool wide open over your shoulders. It’s a great way to have a bit of open neckline while still wearing a warm garment too.

I have the heathered oat version (c/o Everlane) and I love it. It’s crazy soft. It’s merino but it feels like cashmere. I am also really into the camel color. But I also love this soft green sweatshirt version from Alex Mill, which sports sort of a faded, relaxed vibe.

3. Cashmere Cocoon Cardigan

I realize you guys have seen me wear this approximately 1,000 times now. I just wear this thing so, dang, much. It’s very soft, and the shape magically seems to work with everything. I love that the sleeves are roomy, but not too bulky to fit under a coat. And of course, I love this warm, oat color. I am slowly selling off my other cardigans because the cocoon cardigan is all I want to wear. It’s the easiest item to throw on over your outfit when you need a little more warmth. I love that it does not feel heavy, it’s very comfortable to wear.

This one comes with a pretty hefty price tag. I signed up for their email list and used the 15% off code to save. If you want more details on this sweater see my YouTube review.

4. Dark Wash Jeans

This is a perfect example of a stylish and weather-functional item. AND, in case you missed it, deep, indigo jeans are making a major comeback. Don’t get rid of your light wash jeans by any means, but adding a dark pair of jeans to your rotation is a surefire way to add some freshness to your white tees and favorite sweaters. I’ve been wearing Everlane’s Way High jean on repeat because they are so comfortable. But I’ve also been eyeing COS’s tapered high-rise jeans because the shape intrigues me. AND I saw that REIFhaus just released their first-ever jeans, and they are amazing. They are like the nicest version of a jean I’ve ever seen.

Now that we’ve established dark wash jeans are a thing again, let’s talk about why they are good for the rain. I’ve noticed over the years I almost always gravitate toward darker pants in the rain because of the splash factor. It’s easy to kick up dirty water or mud when walking, and even easier to brush up against a dirty car. Dark jeans obviously don’t show that. Additionally, most of the dark wash styles I am seeing are slightly cropped – perfect for keeping hemlines out of puddles and showing off cute boots!

5. Black Boots

I suppose you could substitute any color of boots in here, but I like black because they’re least likely to show dirt and rain, and they make it simple getting dressed. A pair of black boots let me focus on wearing interesting colors on top (if I want) and not worrying if they will mesh well with my shoes (and bag). There are so many styles and directions you could go with black boots. I shared some of my favorites in this post and shared how I’m styling chunky boots in this post.

Today, I’m highlighting a few, simple pairs. The Park Boot by Dear Frances in black, a forever, timeless, city-friendly boot, comfortable for all-day wear. These are the real deal. Freda Salvador makes a gorgeous, water-resistant pull-on boot (use my code 15ANDREA to save). This is on my list to try. (It comes in green now too!) Also, Freda is currently having their friends and family sale, so you can catch most of their boots at a temporary discount. And lastly, the Madewell City Lug Sole Lace-up is pretty awesome. I have these in brown, and I love the zipper in the back, it makes them super quick for taking on and off.

6. Leather Sneakers

Leather sneakers work surprisingly well in light rain. They make canvas sneakers pale in comparison. Most water rolls right off, especially if you take the time to guard your sneakers with a spray at the beginning of the season. I bought a pair of Nike Air Force 1’s and I’ve been living in them. I also bought a pair for my daughter and she often walks home from school in them. They’ve been a great mild rain shoe so far. I also get a lot of wear out of my black Veja’s. Another item that’s both stylish and weather-friendly.

I hope this list has been helpful for you, particularly if you call a rainy climate your home. If you have something to add, do chime in down below!

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