In 12 years of traveling solo for business and not-so-much business purposes, there have only been 3 times that my checked bag was misdirected. But those three times linger with me. I see all the stories about people finding bargains at the Unclaimed Baggage Center and I think to myself that I don't want to see my new dress (or anything else I own) ending up there.
Here are some tips so you can fit 5 days worth of outfits into one standard roller bag.
Pick curly or straight for the week. A flat iron or a curling iron will fit nicely across the bottom of your suitcase up next to the edge. You can buy a small brush - either round or flat - and also use that to style with a hairdryer.
My philosophy is always to start with the foundation - and that means looking realistically at what shoes I'll need for the trip. I limit it to two pairs - and generally, I only take one pair of dress shoes - and that's the pair I'll wear. If I have to take 2 pairs, I plan to wear the bulkier ones on the days that I fly, and I'll pack a nice pair of flats or dressy sandals that I can wear with any of the outfits I'm packing. If I'm going to a hotel that has a fitness center, I'll take my cross trainers. I'll stuff the socks that I'll wear with them inside. The shoes will line the long sides of the suitcase at the bottom.
Here's where you have to be practical - because your shoes will impact every other choice. Black, brown or navy. Make your choice and build the rest of your outfits around that color.
Pants & Skirts
Now that you've narrowed your color choices by your shoe selection, you can pick your pants and skirts. You can easily pack 2 skirts for every one pair of pants, so you can have skirts for each day of your trip. If you're not a skirt girl, you can pack 3 pairs of pants plus a good pair of "travel pants" that you can wear the days that you're flying.
To fold, pull them together like you would if you were hanging them, either in half or on the pleat, and roll them up into a tube. Lay them across the bottom.
In warmer climates, you can pack rayon or silk shirts in half the space that a cotton shirt would take up. Sleeveless shirts are also a good option if the dress code permits (we all can't have Michelle Obama's arms, but wear sleeveless fearlessly nonetheless!).
To fold, either roll or use a traveler's best friend, the Flipfold Clothing Folding Board. You'll find by keeping things uniform, you can save more space. Lay the shirts over the tops of the shoes and pants.
PJ's and other stuff
Anything that's invisible to the outside world can be used to fill spaces. I take a camisole and a pair of shorts to sleep in. They don't take up any space at all. Same goes for socks, nylons, and anything else. If you're taking skirts that are unlined, don't forget your slip! For workout clothing, taking a nylon shirt and short set has the benefit of being easy to rinse and hang dry overnight, as well as being compact and "tuckable."
As for make up, stay sensible. Don't take more than would fit in a quart-sized plastic bag. The less you take, the better!
Use the outside pocket of your suitcase or your other allowed carry-on to stow your quart-sized baggie with your liquids, gels and pastes. You can also throw your toothbrush in there. One time saver for this bag is Downy Wrinkle Releaser, Travel Size Light Fresh Scent, 3 fl oz. You can use it to quickly pull wrinkles out of most of your clothing, and it freshens them up, too!
Let the hotel provide...
Your hairdryer, shampoo, conditioner, and soap. Unless you're really particular, you don't need to waste space on these items.
Fit everything in your carry-on, and you, too, can smile and wave at everyone waiting at baggage claim on your next trip as you stroll on to your destination.