From The Gospel According to Colin Fletcher - Clothing. Paraphrasing because I'm too lazy to go get the book.
Don't carry more clothes than you can wear at one time. Excluding socks. he advocated 3 pairs in red.
There is a corollary between clothes and sleeping bag.
Wayne
Old. Slow. "Smarter than the average bear."
Eddie Valiant: "That lame-brain freeway idea could only be cooked up by a toon."
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I've been backpacking most of my life but I started as a dirtbagger pretty young. I've replaced and refined as time went on so i'm versed in making it fit and making it work.
Presently, everything I need for 7+ days and 3+ seasons in the southeast takes up less than 50L including food. I do a lot of overgrown wilderness and I get secondary contact poison ivy regularly, so I even carry extra clothing so laundry on the trail is possible. With that said, a trip with situational or even luxury gear means both my clothing and sleeping bag fit into the sleeping bag compartment with room to spare in my larger 65L Osprey Atmos. Everything I carry fits into that pack (tent included when I need one) or even one smaller with the exception of the sleep pad.
If you choose clothing and sleeping gear as layered systems, you can get away with a lot more with less weight, bulk, and valuable pack space. For me its the same as any gear choice: multi function and light. Remember the 5 means of heat transfer: conduction, convection, evaporation, radiation, and respiration. When I incorporate my shelter, sleeping, and clothing systems into something interdependent, my weight and volume fluctuate much less and often to my benefit than when I compartmentalize items into individual conditions. I'm always slightly adding or taking away convection, conduction, and radiation to stay cool or warm. I only use wool for socks and a cap. The same goes for the sleeping bag and pad. For example, I have a particular bag rated 55 degrees and super cheap and light, so I sleep in a layer or two and use a mylar blanket around the outside, reflecting my radiation and sealing convection. Usually I use air insulation from the ground, sometimes CCF, sometimes both. With a light shelter and pad, I'm comfortable at or below freezing essentially adding 20+ degrees to the bag with what I already have + 2-3 ounces. If I'm using my stronger (and sometimes unfortunately warmer) shelter during the risks of tornado season, it eliminates more convection loss and I need less insulation. I've gone down to 35-40 degrees with nothing more than my clothes and a mylar blanket and been perfectly comfortable. for the extra 1 lb of a shelter, I shed the 1.5 lb sleeping bag. Winter weather takes a more aggressive approach and some heavier gear, but the basic ideas don't change. In an area of the country where it can sometimes feel like summer at 8am, autumn by noon, and freeze that night I've had to adjust a lot.
So Blah. This is just my style, and it works for me. After a long time, I've also gotten more comfortable with less and continue to do so. Its about what works for you. I sleep warm and stay warm. Hope you do the same! As for the packing part, I found longer, cylindrical shapes work well to pack around a taller thin tent stuff sack. If I load that vertically, I can usually slide the other cylinder-packed things (rolled up zipper bags and stuff sacks, cook pot / fuel, etc) down each side and fluff out the front with flatter stuff. That way I can also slide out my tent through everything first anyway.