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7 Cozy-Casual Outfits for Late Fall / Early Winter

A few times per year, I put together a new fashion post with a handful of looks appropriate for the season. I didn’t mean to start this tradition, but it is one of the most popular posts I put out every time.

What I’ve discovered through these outfit posts is that you are probably very similar to me: you want to look cute, but you also want to be comfortable, casual and keep to a moderate budget. So that’s what this post is all about.

It always feels so silly taking pictures of myself for these posts. It’s just me in an outfit smiling at myself through a mirror into my phone. Ryan walked in while I was taking these photos and I was mildly embarrassed standing there posing :) But I do it for you, my friends.

I know how helpful it is to see how others put outfits together – especially casual, everyday outfits. My hope is that you can use this as a great shopping list for basics and layering pieces, and maybe a few outfits will spark some ideas of how you can mix items you already have in your closet.

A few thoughts before we jump in:

I’m a work from home mom and dressing up isn’t always practical or necessary. My go-to outfits are always a mix of that formula up there (cute, comfortable, casual). I do my best to fill my closet with classic, basic pieces that are easy to wear and can be mixed and matched again and again.

Of course there are days when I wear leggings and sweatshirts (see below) and sometimes that is the right choice. But if you find yourself in a fashion rut, if you have the same frumpy college hoody on repeat or you don’t remember the last time you felt cute in your clothes, maybe now is the time to pay attention to you. I really do believe that getting dressed makes a huge impact on how we feel about ourselves and the confidence we have as we go about our days.

I hope you can use this post as outfit inspiration and a reminder to put on clothes that make you feel cute.

Let’s get started!

OUTFIT NO. 1

A poncho is my current favorite easy layer that elevates any outfit. I’ve worn this one on repeat – with jeans for casual days and with black pants and heels for fancier events. I topped it in this outfit over a simple black jersey turtleneck. I’m drawn to tops with high necks and while turtlenecks do remind me a lot of the patterned versions my mom and aunts used to wear in the late 80’s, I still wear this more updated version proudly.

poncho (similar) | turtleneck | jeans | bag | booties | earrings

OUTFIT NO. 2

I go to barre class at a local studio twice per week and wanted to up my workout/athleisure game. These olive leggings are fun with the x detail at the side and may I kindly and firmly suggest that you get this sweatshirt. It’s thick and soft and covers up the bum.

sweatshirt | leggings | shoes

OUTFIT NO. 3

I have lived in Seattle for all of my adult life (minus a 4-year stint in southern California for college) and have never owned a real raincoat. I have a current crush on olive green and when this went on sale, I ordered it (it’s still on sale!). So far, I’ve worn it to the kids’ football games, to a concert, to church, to dinner, to the bus stop. It was such a good purchase.

Under the jacket for these pictures are a few of my favorite basics: a soft button-up, distressed jeans and copper-colored suede flats.

jeans | boyfriend shirt | rain jacket | flats | earrings | watch (similar)

OUTFIT NO. 4

Of all the outfits in today’s post, this one feels most like me on a normal day. Jeans, t-shirt, puffy vest (to keep me warm) and a hat. When I’m at home, I’m always wearing slippers, but the rain boots are easy to throw on when I head out.

And let’s talk about the hat. I ordered this one as a sample thinking maybe I’d put them in the shop. We decided not to, but I still wear this sample hat all the time. I prefer this trucker style and have a surprisingly difficult time finding a small enough hat for my small head. I linked a similar style below that is a close-ish match to my jdc hat.

striped shirt | down vest (another option)| jeans | hat (similar) | rain boots | earrings

OUTFIT NO. 5

As the days get chillier, I like to wear easy layers. A t-shirt, a soft sweater, a warm jacket. This coat is just polyfill, so it’s not as warm as a down-filled coat, but it works great for our mildly cold late fall/early winter days. Plus, the color is different and decidedly fall-ish.

gold jacket | sweater | jeans | booties | hat

OUTFIT NO. 6

It’s rare, but sometimes I wear something other than jeans :)

I am trying to add more casual dresses into my wardrobe and this one is the newest addition. It fits slim on the top with lots of extra fabric on the bottom (I might have mine taken in a little bit), but isn’t the neckline and fabric a great combo?

dress | boots (similar) | necklace | earrings

OUTFIT NO. 7

These wide leg jeans have been in my closet for several years and I’ve decided to bring them back. I like skinny jeans, but I do think a wider cut like this is more flattering on me. This outfit is another chance to layer, with a denim shirt (I wear mine all the time) and sweater.

sweater | denim shirt | wide leg jeans | boots (similar) | earrings

BONUS!

On those ‘I don’t feel like getting dressed’ days, this is what you’ll find me wearing. Leggings, t-shirt, comfy sweatshirt (I adore this one) and my UGG slippers.


So there you go. Seven favorite outfits to wear this fall/winter. I hope these outfits help inspire you to try new combinations of things you already own and maybe add in a few new pieces that you love!

Do you have any favorites?

41 thoughts on “7 Cozy-Casual Outfits for Late Fall / Early Winter”

  1. Ok I have a question about the denim shirt and sweater. How are you doing the neck of your shirt with a high collar on the sweater.

    These posts always inspire me!

    1. I popped the collar so it would peek through. My shirt has buttons on the front pockets which kinda poke out through the sweater, so it might not be the exact right shirt to wear under this sweater – but I like the color combo of the dark and light denim with the mustard.

  2. These outfits are perfect! Thanks for posting these. They get me out of my rut of always wearing jeans. Not that there’s anything wrong with always wearing jeans, but it’s nice to change it up a bit!

  3. Thank you for sharing! I always look forward to these posts. Can you recommend a boot for a petite lady? I am 5’1 and find it extremely hard to find a boot that looks right on me.

        1. These links are from a few years ago so they are not current. Hopefully this post can be used as inspiration for what to look for in your closet and in stores!

      1. #1 You always look super cute and stylish. But the earrings really add something! Way to go!
        #2 In the picture of Outfit 7, I see a grown up Audrey girl.

      2. 7! Looks comfy yet polished enough for my casual workplace.
        Love that you do these – i liked all your sweaters and the dress, too!

      3. Can you tell me what size you ordered in the dress? I’m 5’6 and weigh about 135 pounds. I’m thinking a medium if it’s fitted at the top?

        1. Yes, a medium would probably be great. You might need to have the sides taken in – there is a lot of extra fabric, but the top is so pretty and i love the pattern. Hope you love it too!

      4. Question the jeans paired with your rain jacket-where are they from? The link takes me to shoes from Target. I’d love to know! Love all your outfits as always thanks for sharing!

      5. I love your style! And your hair! And that your outfits are always very affordable. This year, you need to give yourself permission to buy new boots. :) Those Korkease are still at Nordstrom.

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