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.