I am going on a two week trip in May (starting May 14th) to visit friends in Europe and stopping on the way back to visit my little brother (wrapping up his first year in medical school in St. Louis) to go spend Memorial Day in Chicago. I'm really excited to take a solid two weeks off of work, but I'm not sure how to pack lightly for such a long trip, as I usually just do weekend trips.
The details: I will be in each location no longer than 3-4 days and I'll be staying with friends, so I will have access to a washer/dryer. I'm going to England and Norway where it's very likely to be cold/rainy and of course Chicago is always unpredictable in May, so layers will be important. I'll be in Norway for Norwegian Constitution Day, so I'll need to wear a long(ish) dress/skirt since my friends will be wearing suits or national costumes.
I'd love to take just a backpack (I have a very large one) as there will be a full day in London where I'll be carrying my luggage with me and I don't want it to limit my sightseeing. I dress very modestly (don't wear skirts/shorts above the knee, don't show shoulder, back, cleavage, etc.), but I will be seeing an ex-boyfriend in Chicago, so it's very important to me I look my best :) I'm 5'8", a size 10 dress & shoe, with dark hair and fair complexion.
Tee - These $5 t-shirts from Forever 21 are my new favorite. The loose "boyfriend" cut is trendy but also comfortable to wear on a long flight.
Jeans - Your favorite straight leg pair in a dark wash. Avoid "stretch" fabrics that will start to sag as you travel.
Jacket - In dark linen with little ruffles. Linen is a great fabric for a range of temperatures and looks classy even when wrinkled.
Flats - In gray suede.
Dress - A little red dress in versatile jersey. Casual enough to wear with flats sightseeing during the day or with pumps to get dressed up at night.
Pumps - In blue.
Bring a couple versatile layering pieces, an umbrella and a puffy jacket that packs up in case of cold weather. Anything else you need, you can buy along the way. Including the outfit for Norwegian Constitution Day - see if you can improvise with some borrowed some pieces from friends instead of buying and dragging around things you wont wear again.
Have a great trip!