When packing for a weekend getaway; the first question you have to ask is: what kind of weekend do you have planned? If you are going camping, you are going to want substantially different things from a weekend of fine dining and dancing. So, let us lay this out in a rather generic fashion.
Next, how are you traveling? If you are going by plane, try to use a small carry-on bag. It will make getting through security so much easier. Always bring an extra pair of socks and underwear; you never know when you will need them. Roll them up tight and tuck them in a corner or pocket of your bag. Men’s clothing is rather easier to deal with, so we will cover it first.
Short pants are very easy; just fold them up as small as you can, and lay them in your bag. With long pants, especially a dress pair, folding will wrinkle them. Your best bet is to roll them up. In the case of t-shirts, like short pants, you just fold them up as small as possible. Shirts, whether long-sleeve or short, fold up tight. They and dress pants should be packed more toward the center of your bag, to minimize wrinkling caused by buffeting.
Always try to plan for the unforeseen. As the saying goes: “Chance favors the prepared mind.” So, if you are going off on a fun-filled, casual weekend; include a dress shirt and pants. That way, if you find a nice restaurant you want to try, or get invited to a party, you can dress appropriately. This also means, bring extra of everything! All it takes is a thunderstorm or a stray nail to ruin an outfit. So, three or four pairs of pants, and four of five shirts – that are all interchangeable, are about the minimum you should bring.
With women’s clothes, the same rules apply. Skirts and dresses can be folded or rolled. A lot depends on the quality of the material. A really nice dress, roll up and set in the center of your bag. And, whether a woman or a man, do not forget to pack some pajamas. If you are looking at some sort of special activity (e.g. swimming, mountain climbing, hang gliding), be sure to bring along the appropriate clothing. So, that may mean a swim suit, or climbing gear; whatever you need to make your weekend fun. If you are planning to ski (either water or snow), you are not going to fit them in your bag. So, just carry your skis.
As for shoes, try to pick one all-purpose pair. If you really must bring a second pair, wear the biggest and bulkiest. Put the others in the bottom of your bag, and stuff socks and underwear in them. Finally, when it comes to toiletries, go with the small and disposable. Do not bring your best razor or other items. Instead, buy one of those cheap plastic razors, get a travel-sized bottle of shampoo, deodorant etc.