My husband and I both use Rick's bags- bought them more than 20 years ago and they still look new. We even did an "around the world" trip with just them and a day bag. I don't 'do' dress/skirts for travel (and not much at home either). So I only pack pants. I take a total of 3 or 4. I take a mix of long and short sleeve tops. In Sept. in Europe you could get anything from hot to cold, wet to dry, windy to rainy. It'd help to know exactly where you're going. But in general here's what I'd take:
Layers are what work. Wear on plane: black cotton-blend pants, turtleneck/T-shirt and a long-sleeved or 3/4 sleeve "big shirt" {button up that can look a bit like a jacket}, windbreaker/raincoat with hood, good walking shoes. In carry-on: 2-3 pair black or khaki cotton-blend pants (I am allergic to wool and rather hot-natured), 3-5 T-shirts/turtlenecks (some long sleeve, some short, depending on season) 1-2 "big shirts", optional a sweater/cardigan or fleece -everything coordinates with everything else.
3-5 bras, at least 7 pair undies, same with socks, 1 pair pjs if desired.
I also take hand wipes, stain wipes, small baggie with laundry soap, first aid "kit" in a baggie- band-aids, small packets of Neosporin, dental floss, Advil or Aleve, Benadryl, Dramamine, Nyquil gel capsules, etc., sewing "kit"(various colors thread wrapped around a small piece of cardboard, 2 needles, buttons, safety pins), medications, medical info sheet, copy of insurance info, etc., 3-1-1 bag with small sized deodorant, perfume, shampoo, lipstick, chap stick, toothpaste, etc., another quart baggie with eye shadow, blush, powder, comb, brush, tweezers, razor, clippers, etc. , some "feminine supplies" if needed, wash cloth in a baggie, gloves, hat or hooded scarf in winter. Totally optional- scarves, phone, charger, adapter plug, camera & charger, extra memory cards for camera, paper & pen, extra shoe liners, umbrella, day pack. Hubby gets by with a bit less - no need to duplicate some things. Our bags weigh less than 20lbs each.
Oh- don't take a blow dryer, curling iron, straightener, etc. Even with a voltage converter and plug adapter they often don't work well 'over there'. Style your hair simply and use the provided blow dryer.
And another note- your pills DO NOT HAVE TO BE IN THE ORIGINAL BOTTLE. That said, it is always advisable to have the correct info with your medications in case of illness, emergency, needing refills, etc. Ask your pharmacist to print you an extra label and put it on a small Ziploc bag, then put the medication in the bag. Alternatively, some pharmacies will prepare blister packs with all your meds grouped according to when you take them (example, day 1, am in one blister, day 1 lunch next, day 1 pm next, then day 2...) and put all the labels on the top of the sheet. You could also use a pill organizer and put the labels from the pharmacy on one sheet of paper taped to the bottom of the organizer. Lots of ways to do it. I also carry an information sheet with all of my medications listed (both generic and name brand), the dose I take, when I take it and what condition it is for. I also list my Dr.'s phone #s, pharmacy's #, and emergency contact info as well a list major medical conditions (I have asthma, high blood pressure, PCOS, etc.) and surgeries /dates. This info sheet has come in handy when I had a severe asthma attack at work (the EMTs knew everything they needed even though I had trouble speaking). If you become ill while traveling, or need a refill because you lost meds, etc. this could be vital.
Feel free to private message me if you want a sample copy of the info sheet. Also, liquid meds should NOT be placed in your 3-1-1 bag, but should be in their own baggie, and in the original bottle. You must declare them to the TSA before screening.