Wool in all forms
On the day I wanted to take these photos I was wearing this wool skirt from Madewell. I found it on sale just before Christmas and was so glad I snagged it because I think it is going to quickly become my favorite colder weather skirt. Since it's wool and is a heavier material, even though it's above the knee, it is a bit warmer than say something made of chiffon or cotton. Plus, doesn't it just kind of look like Portland? (Anything grey makes me think of Portland) The second kind of wool investment (aside from socks) I would recommend are lightweight sweaters, such as this Merino wool turtleneck from J. Crew. The wet kind of cold that exists in Portland chills me to the bone some days so it's really nice to have a warm wool layer that I can snuggle up in but that isn't going to be too thick underneath my jacket.
Plaid/Flannel
Plaid is one of the easiest patterns to wear and is something that I think really works with kind of personal style aesthetic. It's just as easy it make a plaid shirt look preppy as it is to make it look punk or hipster-ish. Two ways that I find myself wearing plaid a lot are either in the form of flannel shirts that I like to tuck into one of my many pleated skirts or as a scarf wrapped around my neck and tucked into my leather jacket. It's an any season, any style, any article of clothing pattern that I think should exist in some capacity in everyone's wardrobe.
Weather Proof Shoes
Okay, let's talk shoes. For me, I like to stick with investing in classic shoes that will go with everything and last through anything. That means either leather or some water resistant material, things that are either flat or have low heels, and are well made. My two suggestions are these chelsea style rainboots from J. Crew (so much easier to wear than full on, knee high, rainboots in my opinion) and some black leather flats from Born. I have so many pairs of flat, black, leather shoes because they just go with everything and Born is one of my favorite brands for shoes that are practical and still stylish.
Black Tights
These are basic, but important! I like to wear dresses and skirts year round but usually it isn't warm enough to always go bare-legged so a good pair of black tights is essential! I like these because they are designed to stay up better than most and these because they're fleece lined and extra cosy.
Big Hats
Weather in Portland usually lies somewhere in the middle of raining and trying to be sunny, which generally leads to me having a lot of unpleasant, frizzy, and damp hair. Hoods on rain jackets only kind of fix this problem, but they can really only be employed when it is actually raining outside (plus my hot pink north face rain jacket does not go with a very large percent of my wardrobe) so my go-to solution to this problem is hats. Large felt hats in particular. They make any outfit look more chic, they hide unsightly hair issues, and they keep my head/hair/face area mist free! and that is all I can really ask of an accessory.
Jackets
And that's it! Those are my Portland wardrobe essentials - I hope they were interesting/useful to you all in some capacity. Outfit posts are on the way!
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