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I always over pack a little. For domestic trips lasting 7 days or less, I have a roller (the max size allowed by most airlines for carry on) and a backpack. Both usually stuffed. For overseas trips or domestic trips lasting more than a week, I pack a duffle or larger roller in addition to the backpack and smaller roller.
I'm a guy in my mid 20s. I typically have at least one suit (even for leisure trips), two pairs of jeans, a few tee shirts, a few dress shirts, dress shoes, running shoes (love morning jogs in strange cities... a great way to explore), and casual shoes. Weather permitting, I may have a single pair of cargo shorts as well as more "stylish" shorts and topsiders and flip flops. I ALWAYS bring underwear for each day and one extra (you never know). Same for socks (and obviously a pair of dress socks).
The big space hog for me is my camera gear. Even when I pack lightly, I have a tripod, the camera body, a general walkaround lens and a lens dedicated to something more specific (i.e. macro lens if flowers are in bloom, or wide angle for a trip I know will have good views). That takes up a lot of room.
So no... I don't pack light. I feel better if I pack too much and bring home clothes I haven't worn than if I don't pack enough and am stuck without a convenient outfit.
When I was traveling EVERY week, I would heavily utilize hotel laundry or drop-off services. That is, I would drop my laundry off on Friday on the way to the airport and pick it up on Monday when I got back. I would just carry my computer and my briefcase.
I'm always impressed by those ultra-light business travelers. They come fully prepared for meetings and demonstrations -- computer, literature, professionally dressed without a wrinkle. I'm also impressed by the light traveling hiker-camping types who even carry a tent and sleeping bag in a backpack.
I'm getting better but I still seem to always manage to bring along somethings I don't end up needing. My next purchase is going to be a 7" tablet so I don't have to carry along a laptop -- I think -- because I sometimes have to vpn into work and am not sure how that would be with only 7".
I've always travelled light. I'm in Mississippi right now, visiting family, and I packed all my stuff in a small backpack, and a small duffel (about 12"x12"x24"). In the duffel, I have 5 changes of clothes, and an extra pair of shoes. In the backpack, I have my laptop, charger cables, and a folder of some paperwork I needed to bring with me. I never pack toiletries. The regulations are just annoying (3 oz rule, clear plastic baggie), and it's just easier to buy things at my destination. I don't pack books, cameras, or mp3 players. My phone does all of those things, and fits in my pocket.
Here's a suggestion: roll your laundry. Pants, shorts, shirts. Everything. Rolling clothing prevents wrinkles, and compresses them, meaning they take up less room (so you can fit more in your suitcase). People around the globe do laundry, why should you be an exception? Flying back with dirty laundry sucks, especially when you only have a carry-on (nothings worse than a smelly carry-on). But, doing laundry every day is tedious and time-consuming. My rule of thumb is to carry 5 changes of clothes. Including the clothes I'm wearing, this gives me 6 sets. All of my clothes are very neutral. Jeans or Khakis, and plain shirts. I usually pack one or two button downs (buy the nice ones, that stay wrinkle free. I don't like to iron). Don't pack clothes that "have to go together". All of your wardrobe should be mix-and-match. With this set-up, I can go 5 days between washing clothes, and don't look like I'm wearing the same sets of clothes day after day. Shoes depend on the destination. Usually, it's a comfortable pair of walking shoes, that I can easily take on or off (currently, I have a nice pair of sperries). If I pack a second pair of shoes, it's something like sandals, hiking shoes, or dress shoes (depending on the destination).
Dress in layers, and plan according to your destination. If I'm going someplace tropical, I'm not going to pack long sleeves. If I'm going to a more temperate destination, where weather might get colder, I'll wear a light jacket. Buy one that's light, but warm enough. I'm a fan of waffle-weave zip-up hoodies. I'm perfectly comfortable with one over a T-shirt, even in deep snow. When it warms up, I can unzip it, and it packs up nicely in a daybag if I get too warm. Wear it on the plane, don't pack it. You can wad it up and use it as a pillow, or use it as a small blanket, if you don't feel like wearing it.
When flying, your trip becomes a lot nicer if you get through security quickly. Wear shoes you can take on and off easily (with one hand), and quickly. Get a good laptop bag, that has a separated pocket for your laptop. Put your laptop inside of a laptop sleeve, in this pocket. When you get to the scanners, you can quickly slide your laptop (still in the sleeve) out of the backpack, and toss it in one of the bins. When you get past the scanners, the separate pocket makes sliding the laptop (in sleeve) back in the bag very easy. Put your phone, keys, change, and wallet in your backpack. You don't need these on your person. Keep your photo ID and boarding pass in your hand at all times (I usually even carry them through the scanner). You will need these, and you do not want to lose these.
If you're flying overseas, get a small passport holder that you can wear around your neck. Keep your passport, and some cash in this, and nothing else. Wear it during most of your trip, underneath your clothes. As long as there's no metal, you'll be fine going through security with it under your clothes. The agents know what these are, they've encountered them thousands of times before through their line of work. Exchange currency wherever you find the best rate, and keep local cash on hand. American dollars won't buy you anything in Europe.
Don't carry food. Drinks you'll have to toss at security. Food is bulky, takes up a lot of room, and can be found in most places (yes, even socialist Europeans eat food). You won't starve.
My most important advise: Carry a pack of gum. If you get nervous on flights (especially in bad weather), chewing gum helps calm you down. Another benefit of gum? Children. Thankfully, I don't have any. Unfortunately, other people are determined to bring them onto the airplane. This is generally regarded as a bad decision. Many younger children yell and scream during take-off and landing, because they are not accustom to "popping" their ears during pressure changes. While we all know the "hold the nose and blow", kids don't. Another way to pop your ears, though, is moving your jaw. What's a great way to get a little kid to move their jaw? Give them a piece of gum to chew.
I don't know how many times this has saved my sanity during a flight. When a nearby parent is trying to deal with a screaming child, get their attention, and ask if you can offer them a piece of gum. They, in a frantic mood trying to get their kid to sit down and be quiet, will be willing to try anything at this point. They will gladly accept your gum offer, usually tear it in half, and offer it to the child. The child will begin chewing, and INSTANTLY shut up. It's actually pretty amazing. I've legitimately gotten a round of applause from nearby passengers after shutting up some particularly loud children. Make small talk with the parent, and find out if they have any connecting flights. If they do, offer them more pieces of gum to carry with them (2 pieces per flight is usually good). They will accept your peace offering, and passengers on their connecting flight will silently thank you.
I'm female and traveled around Ecuador and Peru for a month last year with only a ten pound daypack. It was a bit of an experiment for me, and wound up being a revelation. I'll never pack heavy again. Unless you're going to a cold place or need specialized gear you only need a few toiletries (which are easily replaced as you use them) and maybe three changes of clothes, a light fleece sweater, rain jacket, and maybe two hats. You can do laundry in your room if you want, but I had no problem finding cheap laundry services that would wash and fold all my clothes for me while I was out. I'll happily wear the same clothes repeatedly in exchange for the freedom of carrying such a light bag.
@tigre79: I envy you! I plan on doing something like that on my next trip -- carrying just a small, light daybag. My description above is me "traveling heavy". I believe I could easily travel on 2 or 3 changes of clothes, I just haven't had a good opportunity to do so. When I went to NYC last summer, I was gone for a week and managed with just a small hiking backpack, though I carried a lot of "extras" (blanket, small travel pillow, and some food items -- I rode the Amtrak, instead of flying, so food was actually a good thing to pack then). I'm sure with your Ecuador/Peru trip, you realized the benefit of packing light: ease of travel. When all you have is a backpack, you don't have to worry about keeping up with that big rolling bag. You don't have to plan long layovers, to make sure your checked luggage makes it to your next flight. You have the security of being able to be with your luggage at all times, and increased mobility. With just a backpack, you have free hands (no longer fumbling for door handles, keys, etc), and it's much less stressful.
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