What’s In My Weekend Bag: Portland Edition

Many of you don’t know this because I talk about Seattle so much, but I was actually raised in Oregon. Hillsboro, to be exact, which is roughly 20 minutes outside of Portland. I’m beyond excited to go home for the weekend this week. It’s long overdue!

Portland in December is freezing at night, so I’m packing pieces that are comfy, practical, and still cute enough for coffee shop hopping, bookstore wandering, and tax-free holiday shopping. Though this style of blog post is different for me, let me know if you like it in the comments below – and if you like this kind of post, don’t forget sign up for my newsletter!

_{Affiliate Note: Some of the links below are affiliates – this means I may earn a small commission if you make a purchase, at no extra cost to you. I also love using ThredUp to fill gaps in my wardrobe. Thrifting is a passion of mine, and it’s a sustainable way to find unique, budget-friendly pieces.}

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What’s In My Weekend Bag: Portland Edition

Ah Portland, known for being and remaining a little weird. One of the cities that invented the hipster and has an underground grunge following that’s a bit more froggy-er than its neighboring big city (Seattle). Though it’s home to an annual naked bike ride, I will be fully clothed through the entirety of the weekend as temperatures are expected to be around 50-56° F and rainy.

Portland Clothing Essentials

Fleece-lined leggings — perfect for staying warm while exploring
Long floral skirt dress + crop knit sweaters — layered for both warmth and style
Wide-leg jeans — comfort for walking the streets all day
Thrifted Nike 3/4 zip sweatshirt — cause car rides should be comfortable and warm
Workout Clothes – it’s the holiday season, we gotta work it a little more than usual
Madewell chunky black boots & Brooks walking shoes — stylish but practical for city exploration
100% virgin merino wool beanie — a gift from my mom during our trip to Bath
Beloved black leather crossbody — matches everything and is so cute
Puffy black parka — my winter staple, also trusty from the prior two years at the Christmas market

Accessories & Extras:

Flat iron — essential because I go 3-4 days without washing my hair
Toiletry bag — packed and ready (note to self: write updated post on essentials!)
Away carry-on luggage — practical, fits all planes worldwide, and comes with a lifetime warranty
Book + Handmade Book Sleeve — because we’re reading this book for Book Club this month
Mini Travel Journal — purchased in Scotland and ready for all of my crazy travels
Vlogging camera — maybe someday this footage will make it to YouTube!
Reusable coffee cup — Portland respects your caffeine habits

A Portland winter weekend calls for comfy layers, practical shoes, and a few special touches. You guys, for real – ThredUp has been such a breath of fresh air and has really helped me keep my travel wardrobe sustainable while still being able to get out for adventures.

What are your must-haves for a weekend away? Drop them in the comments – I’m always looking for inspiration for my next city escape!