I always have the same problem whenever I travel: I pack too much and don't wear half the stuff I bring. On my currect vacation, I am away for a month, so intelligent decisions needed to be made. I packed weeks in advance to make sure I packed what I needed, no impulses. Some voyaging rules...
1. Pack clothes that can be layered. Simple dresses are the easiest things to layer - shirts overtop, sweaters overtop, tights underneath, skirts underneath, even other dresses overtop... You can mix a simple dress with so many other clothes that no one will know you're actually wearing the same thing over and over again...
2. Pack clothes in basic colours. Blacks, beiges, navys, olives... Even basic patterns like skinny stripes... If you lay your clothes out on the floor before you pack them, and there is a general colour palette goin on, then you won't have a problem creating many outfits or layering your items.
3. Pack at least four pairs of shoes. Seriously. Casual sandals (like beach sandals that can get wet or mucky), fancy sandals (that could be worn out to dinner if need be, and if you don't feel like wearing heels), heels (because there will def be a time when you'll want to be dolled up), and some sort of loafer/covers-your-whole-foot shoe (because if it rains, sandals don't cut it).
4. Pack nice clothes. Don't opt for "comfy" clothes just because you are traveling. To me, a loosely-fit cotton dress is just as comfy as sweatpants, yet looks a million times better. The trip I'm currently on, I packed my nicest things, so I have no choice but to look good and put together.
5. Pack beforehand, then eliminate items you might not wear. Then go through your stuff again a few days later, and eliminate some more. If you're like me, you'll probs shop a lot wherever you are, and you'll be thankful to have a half-full suitcase going there and a full-to-the-brim suitcase coming back.
Black slip: Club Monaco. The easiest thing to layer, ever
Dress: Wilfred. As comfy as pyjamas
Shirt: Tommy Hilfiger. A fancy top, dress up or dress down
Shirt: TNA. Basic stripes, easy to throw over
Blazer: Talula. A light jacket easy to layer as well
I cheated a brought six pairs. Matiko studded loafers, Ralph Lauren heels, Puma runners,
Camper sandals, Banana Republic sandals, Old Navy sandals
Other essentials: Mac eyeshadows, Neutrogena Ultra-Sheer sunscreen, John Frieda Frizz-Ease smoothing hair cream, Ray Ban clubmasters, and lots of jewelry
Mac colours: purples, pinks, creams and golds. Looks perfect with a tan