1. Pick Out Your Favorite Things
You're on vacation! There will be more pictures of you during these upcoming days than you've taken in the past month, so wear things you've been saving for those nonexistent "occasions." Allot a maximum of one favorite item per day that tickles your fancy and lay them all out on your bed. Then assemble all your best fitting staples and see how many fancy-ticklers you can pair with the each one. Pack only the staples that will go with more than one of your chosen pieces and try to make sure that each one has a different purpose.
2. Check The Forecast, Pack Layers and Leather
The weather can change as often as you do, so I recommend plenty of layering options that you can wear multiple times. Don't worry, no one will notice. Bring a leather jacket too. It’ll break the wind, keep you warm, save all the suitcase room your down parka would hoard, and can double as a light jacket for an innocuous spring breeze. Things like knit hats, leggings, wool undershirts and scarves are invaluable in an unexpected cold patch and take up hardly any space.
3. Wear Wool
All hail the technology of nature. Wool is comfortable, breatheable, repels stink and sweat, keeps you cool in summer, and warm in winter. You can even wash your baselayer wool in the hotel sink and it will air dry more quickly than you think. Today's SmartWool is the antitheses of scratchy. Invest immediately in an obscenely soft wool undershirt to wear under your less washable clothing and you will come home with a suitcase full of freshness.
4. To Pack Light, Pack TightIt defies all reason, but rolling your clothing before shoving it into your case actually does reduce its cargo space. If you fold everything in half longways, flatten out, and roll carefully, wrinkles should be scarce. You can even shove underwear and socks into hats and shoe cavities. If you have a large suitcase take care not to pack too densely, as most airlines will charge a sizeable fee if a single suitcase weighs over their limit (usually 40 or 50 lbs).
5. The Power of Accessories
Accessories are excellent for space-economic styling. What if you decide to crash a cocktail party? Your rhinestone hairclip might be just the thing to transform your go-to sundress from picnic to cocktail. A comfortable romper that you are tempted to wear every day can be easily transformed with a statement belt or a floral scarf. Don't skimp on accessories if you are the kind of person who likes to change it up without being weighed down.
6. Shoes Are Bulky
If you really must bring those over-the-knee cowboy boots, plan on wearing them to the airport and on the plane both ways to save space. Low profile flats are space savers and good to have in your purse when those sandals you thought were comfortable start eating away at your ankles. It also couldn't hurt to make sure the heels you bring are versatile enough to wear with jeans or a cocktail dress.
7. Economy of Space
Plan for the unexpected and stretch out what you’ve packed with a little finesse. Maybe your hotel doesn’t have a pool, but what could it hurt to bring a tiny little swimsuit in case you meet some kids who propose a late night dip? Consider bringing a one-piece instead of a bikini in case you want to wear it as a bodysuit with your high-waisted skirt. Perhaps you have a semi-formal event to attend. See if you can't make a formal outfit from separates that you can wear again, uh, separately, dressed down for brunch or a walk on the beach. When in doubt, remember to pack only multi-taskers; like a small cloth bag or two to wrap your shoes, hold your dirties or bring home extra shopping in.