What to Wear: Oregon Date

What to Wear: Oregon Date

I’m hoping you can help me get a wardrobe together for a weekend in rural Oregon at the beginning of April. I’m on my way to meet (for the first time!) a potential romantic interest. We have a mutual friend who connected us, and we’ve been e-mailing since September ’09 and talking on the phone since January ’10. We’ve seen pictures of each other on Facebook, but I’m still hoping to make a striking impression.

Our activities will include touring vineyards, hanging out, etc. He is a winemaker, so he definitely doesn’t “dress up.” I’m a girl who wears mostly dresses. I’m curvy, with big breasts, hips and thighs and a smaller waist in the middle. It will still be cool outside and probably rainy. Do you have some ideas for what to wear? I need to be practical, but I want to be cute, too! Dresses look better on me than pants, so if I could work in some tights or leggings with boots, that might work.

Very romantic! Here’s one idea for a versatile outfit that combines your girlie style with Oregon’s outdoorsy aesthetic:

Tunic: A classic white blouse tied at the waist will accentuate your curves. Top it with a wool coat if it is cold.
Jeans: Skinny jeans are less scary when worn like leggings tucked into to boots.
Boots: A classic pair of Frye boots. If it is hot, roll up the jeans and wear sandals instead.
Scarf: A bit of spring-y yellow.
Sunglasses: Aviators from Forever 21.

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There are 5 comments for this article
  1. Shelly at 4:29 pm

    So is this part of rural Oregon the Willamette Valley? I went wine tasting there a couple of years ago (it was so much fun!)in April and I think Emily's suggestions are spot on. I will say that it was cool but not cold and drizzled for a large portion of the time we were there, so I would suggest a cute rain coat or umbrella to go with your outfit.

  2. Kate F. at 6:17 pm

    And check the weather report before you leave! I grew up in Eugene, and my parents still live there; the temperature this time of year can really range…Today it's 67 and sunny; in a few days it will be mid-50s and raining. (I hear a lot about the weather, daily, from my mom, who seems to think continual reminders about how much better it in in Oregon vs. Massachusetts will suddenly make me move back?)

    If it's sunny and dry (lucky girl!) it will cool off a lot at night.

  3. Kristi at 4:16 pm

    Emily, this is a great look and just perfect for that area! I always love your What-To-Wear's.

  4. Samantha at 3:38 am

    I want an update on how the date goes! Emily, you should make that a requirement. 🙂

  5. Anonymous at 4:24 am

    Yes, this is Willamette Valley. This is a weekend long sort-of blind date (I've seen pictures of him, so I know what he looks like). Emily, thanks so much for your help! Much appreciated. I will let everyone know how it goes.