What I had in mind was to be practical and pack as efficiently as possible, while being somewhat-stylish.
1) I packed light because dragging our luggage in and around 4 different cities is not fun. We didn't rely on cabs because most of the hotels we stayed in were within walking distance/easily accessible from transportation hubs. I was able to fit everything into one carry-on sized suitcase (rolled items to reduce wrinkles and save space) and a Longchamp Le Pliage large tote. I also stored a folded tote in one of the pocket compartments of my suitcase, just in case I needed extra storage on my return flight home. My one suitcase worked out for the best because we often had to go up and down flights of stairs (no elevators/escalators around.)
2) To dress appropriately for the weather. I learned my lesson the last time I went to Japan in December and had only packed a leather jacket and a sweatshirt as the heaviest layers (face palms.) From my research, I was prepared for colder weather in England and France, but warmer weather in Italy. Expected May temperatures ranged from 55-80 degrees Fahrenheit across those three countries. There was also a high probability for rainy days.
- Cold weather days: sweaters, sweatshirt, long-sleeve tops, jeans, scarf. I avoided packing duplicate items in the same colors (ie: didn't pack two pairs of blue jeans), figuring I wouldn't have a problem re-wearing items.
- Warm weather days: t-shirts, shorts, skirt, dress, flip-flops. As much as I love light-colored bottoms, I knew it would be hard for me to keep them clean for a long duration, so I stuck to dark colors. One pair of shorts and one skirt ended up being sufficient. I packed three t-shirts because they're great layering pieces under long-sleeves or would work as standalone tops on warmer days.
- Rainy days: small-sized umbrella, water-resistant jacket with a hood. I chose a lightweight jacket because I didn't mind layering sweaters and long-sleeves underneath for extra warmth. The thin jacket could also be easily rolled up and tucked away in my tote when I don't need it. The most important thing for me was choosing a jacket with a hood because I don't like getting my hair wet.
Of the 24 items* I packed, I ended up wearing every single piece at least once; many I wore several times by either repeating outfits or by slightly changing an item here or there. The key was to pick basics from a color scheme that are easy to layer and mix-and-match. Along with "neutrals" (denim, white, gray, black), I stuck to variations of reds/yellows/blues -- any combination of the three are colors I could create outfits around.
shirt: J.Crew Factory / wrap top: lucy (similar)
shorts: J.Crew Factory / skirt: J.Crew Factory (similar)
dress: J.Crew (similar; similar)
blue scarf: C. Wonder (similar) / floral scarf: J.Crew (similar)
necklace: Ann Taylor (similar) / ring: Elizabeth and James / necklace: J.Crew Factory
flip flops: Old Navy / wedges: Loeffler Randall / flats: Sam Edelman / loafers: Gap (similar)
I ended up wearing more outfits on vacation, but didn't take full-length photos of them all. Of the 12 outfit photos below, some are only "different" because I added a jacket... so technically there's only 9 outfits.
One last topic I want to touch upon is how I packed my camera for vacation. I normally carry my camera around in a triangular camera bag, which has plenty of padding, is bulky (though doesn't have enough room to store an extra lens), and has a zippered opening. I was looking for something smaller that can fit inside my purse and with easy access -- kind of like a purse organizer for cameras, if you will.
Camaroo camera inserts were exactly what I was looking for. These inserts are available in five sizes, which should be suitable for most cameras out in the current market: compact, micro four third/mirrorless, DSLR 1.0 (what I bought), DSLR 2.0, and DSLR 3.0. I just measured my camera's dimensions and chose the insert that is slightly larger.
Additional electronic items that I also stuffed into my suitcase include: different types of adapters (one for England, one for France/Italy) and a power strip (many hotel rooms only had one available outlet.)