Travel Style: What I Wore for A Weekend in Bend

I traveled to Bend, Oregon this weekend to visit my sister and head to Smith Rock Ranch Pumpkin Patch for a 2nd annual family trip. The weather was projected to start out in the 70’s and end up in the 50’s so it was all about smart layering (ie: one good lined jacket, a cotton & wool sweater, and some good foundation basics). Here’s what I packed for my 4 day trip with a carry on.

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My Packing List

JACKETS

  1. A lined trench from Baukjen (5+ years old) (similar options here)

  2. An oversized cropped bomber jacket sourced from a local San Diego boutique two years ago (similar linked here, size down)

SWEATERS

  1. Molli striped sweater

  2. Clare V. Sweatshirt (older)

TOPS

  1. Black Tee from Sold Out NYC (code CONNITWENTY for 20% off)

  2. White Tee from Sold Out NYC

BOTTOMS

  1. Reformation Mason trouser pants

  2. Mother Ditcher Crop Straight Leg Jeans

  3. Frank and Eileen Monaghan Jeans in black

SHOES

  1. Flattered Bodil black ballet flats

  2. Madewell Lug Sole boots

  3. Freda Salvador Brown Spazzolato Elba loafers (code 15CONNI for 15% off)

JEWELRY

I’m always wearing Thatch necklaces + earrings as my everyday wear jewelry

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Travel day (Day 1 )outfit //

Crop Straight leg jeans // Freda Salvador Elba Oxfords // Trench Coat (old, similar linked) // Belt // White tee

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Day 2 Outfit //

Jeans // Shirt // Bomber Jacket (similar option linked here) // Lug Sole Boots // Bag

favorite spots in bend

📍Dudley’s Bookshop

📍Looney Bean Coffee

📍Wren and Wild Clean Beauty 

📍Sparrow Bakery 

📍The Lemon Tree Cafe 

📍Cafe Des Chutes

📍Mud Lake Studios

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Day 3 outfit

Trench Coat (similar option here) // Striped Sweater // Trouser Pants // Ballet flats // Bag

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DAY 4 outfit

Jeans // Sweatshirt // Shoes // Trench Coat (similar linked here) // Bag + Box Chain

Tips for efficient travel packing

Whenever I am packing for a trip, I always set out 2-3 of my favorite pieces (or more, depending on how long I’m going on a trip) and then I push myself to develop at least two outfits out of those pieces. I pull in a piece to tie it together, I take out a piece if it’s not coming together or if it is too complicated, and then I finish it off with a bag or two. I typically end up with a narrow color palette that helps it all mix/match and then I bring in personality with my layer(s) + shoes. Here’s a great video of how I do it.

If you need help travel packing, or outfit planning for the holiday, you can book a “Shop Your Closet” outfit planning session and we’ll spend 1.5 hrs putting together 10-15 outfits for all your upcoming events.

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