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Four Cute Jackets And Sweaters – Easy Outerwear For Cozy Holiday Timesssssss

We are headed out today to go to the mountain house for the holidays (so excited) which means we had to ship all presents down (which means we are done!) and packing super light – just cozy clothes for hanging at the house, going on walks, playing in the snow, and the occasional visit to my favorite place – Skypark Santa’s Village (You know, the vintage year-round Christmas themed adventure park that was renovated 10 years ago and is just so sweet). Madewell reached out for a social partnership where I tried on and chose some pieces that I wanted for the trip and I figured I’d show you my favorites here.

Wool Sweater Jacket | Cali Demi Boot Jeans | Boots

When I saw this online I didn’t know if it was boiled wool, stiff, etc., but I’m very happy to report that it’s a sweater shacket (a swacket?). It has a lot of stretch but is still tailored and extremely way cozy. So it looks like a boiled wool situation, but it’s a knit if that makes sense. It’s solid and something I’ve been wearing a lot since I got it (I didn’t end up getting the expensive one from Rails that I loved, and this one is way more affordable).

Polo Sweater | Classic Chain Necklace Set | Cali Demi Boot Jeans | Boots

This sweater is super solid for those of us who don’t want anything too fitted right now, and yet it’s flattering. It has slim arms, but lots of room in the bust/tummy with a really good length (not too short not too long).

Puffer Pullover | Cali Demi Boot Jeans | Boots

This was a solid and fast hell yes” for everyone in the room. Super lightweight, easy to pack, pockets, flattering, looks cool, warm, etc. It’s just good.

Turtleneck Sweater | Cali Demi Boot Jeans | Boots

I’m not much for a turtleneck sweater (what with the large love pillows) but this has a boxy cut. Now that I’m looking at the photos I still don’t think I’m a turtleneck sweater person (the striped one above is so much more flattering on my body type IMHO). It is boxy with slim arms, super warm, and very classic.

Coat | Turtleneck Sweater | Cali Demi Boot Jeans | Boots

Lastly, I layered on my favorite trench which I’ve been wearing on repeat since I got it. I literally just wear it over my black athleisure, throw on some boots and I look like I’m pulled together (I suppose this was the initial appeal of the trench coat, right? It covers so much of you that you don’t have to wear an actual outfit underneath.

I’m rushing to pack for our trip and today (Friday) we have FINAL INSPECTIONS!!! I see the inspector walking around the house now and begging my dogs not to bark at him:) This means that all of the chain link fencing on the property (to protect the tree routes during construction) can get taken down as well as all the stickers on the windows (to prove energy efficiency, etc). It’s actually a really, really big deal after a 2-year renovation. ARCIFORM and I should celebrate!! Having the chain link fencing removed is visually incredible – they were around every single pretty tree (and some of the ugly trees) and make it so hard to really visualize how incredible the property is going to be. More to come in 2023. xx

*Photos by Kaitlin Green

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1 year ago

Turtlenecks are only good for layering IMO. Looks great with the coat. You look like you’re all set for winter.

Rachel C
1 year ago

Love all these! I have a suggestion. I really appreciate when bloggers include what sizes of the items they are wearing in pictures. It helps immensely. Just something to think about for future fashion posts!

Heather A
1 year ago

That turtleneck sweater looks AMAZING on you. What are you talking about? Have a great holiday lady!

1 year ago

I bought those boots a couple months ago. I really like them, but heads up- use the pull tabs to put them on. The elastic panel tore from the leather the first time I put them on because I tugged on it. They are holding up well otherwise, but not A+ quality.

1 year ago

What, pray tell, are love pillows?

1 year ago
Reply to  Lynn


1 year ago

I love this! Next time, it would be great to know what sizes you’re wearing. I love Madewell but their sizes are so unpredictable—I was just in the store yesterday (everything is half off!!) and purchased two shirts, literally one size L and one size XXS. I like their boxy cuts, but their tops/jackets are hard to order online without having a size guide!

1 year ago

Why are you shipping presents just to literally ship them right back to your home in Portland a few days later? Wouldn’t it make more sense stress & environmental impact wise to just wait to open gifts until after returning to Portland? Or before your trip? I am so tired of the hypocrisy present in this blog when it comes to wanting to be an environmentalist/not super materialistic and yet here we are with another shopping post and unnecessary shipping of packages all over the place. If you aren’t going to do big changes for the environment than stop trying to pretend you will.

1 year ago
Reply to  E

Hoping for more love and grace this holiday season – and extending it to this fellow reader. I can imagine it’s quite tiring and difficult to be incensed by so much. I admire Emily for showing she is human and doing her best, and not pretending to be perfect (for which I am certain none of us are) and sometimes it means not always being consistent. From an environmental standpoint – sending her gifts can hardly be the big change that will change our climate crisis from a greenhouse gas and carbon perspective. Not defending – just trying to direct the rage against the right machine? Are we all willing/able to live in a big city in a passive haus/Platinum LEED building, walk everywhere and be part of a farm share or community garden? I did, but I assume a person in a yurt would think I could be more “green.”

1 year ago
Reply to  Jaycee

Was originally meaning to comment that I got my shacket and loved it. They only have XXS and XS now. For future reference for similar oversized tops, I end up getting XXS. For reference – I think this long item in XXS can work for those petite in height without being too big, and probably under 115lbs or so (perhaps size up if you are hourglass or want to fit thicker sweaters underneath without feeling tight around arms).

1 year ago

Anyone else have trouble with the puffer pullover link? I get no site found errors, likely Safari preventing data tracking. But I also can’t find this item when I go direct to Madewell and search for it…

1 year ago
Reply to  Michelle

Worked for me, but it’s only available in limited sizes now.