I love reading about how people pack for a trip. I definitely tweek out on packing usually a week before my departure day. It's funny because I actually like doing it. I kind of get a kick out of organizing a week's worth of outfits in my head. Usually I'll make a list of items I want to bring, and start narrowing down to essentials. I always try and bring carry-on luggage only. I hate checking in things. I have this fear that they'll lose my luggage and I'd be so bummed if that happened. Anyways, my last trip to New York, I only brought carry-on and my friends were totally buggin. They couldn't believe I fit everything in my carry-on. So here's my take on packing a 1 week spring/summer trip to a city.
2 V necks/t shirts in neutral colors
3 skirts. poufy, pencil, printed
1 pair of jeans
3 tops. dressy and casual.
LBD
1 pair of shorts
1 pair of black tights. (Just in case! They don't take up any room in luggage.)
black blazer
4 pairs of shoes. 2 heels, 1 sandals. 1 sneaker-type.
bag of accessories
clutch/small purse
hat.
and of course, sleepwear, undies, toiletries

For me, I wear lots of skirts and dresses. I rarely wear jeans, but I will either pack 1 black pair, or wear them to the airport, if I don't wear leggings. I like to mix and match my v necks with my skirts. I usually will go out every night or almost every night, so being able to wear the skirts for both day and evening is ideal. I will wear my flats to the airport along with some kind of tunic, a cardigan and I'll throw on a scarf.

If you can believe, all this fits into a carry-on. I have a Betsey Johnson duffle roller similar to this one. I like to have crazy colored luggage (much more fun than plain ol' black). When packing, i put all of my shoes on the bottom first, then roll each piece of clothing (to avoid wrinkles AND save space). Place all liquid-y products in small containers and leave it the last to pack. It's easier to take out while going through security. I also bring a personal bag that doubles as a backpack, so I can have my arm free to hold other shit, like airline ticket, drink, book, iphone, etc.
Yes, that's a Twilight book.... No judging!
Next time.....sun/outdoors-y trip packing post.