I go on with the basics...
Gear, clothes and equipment (I will do a few postings on that)
Always think in layers from close to the body to further apart. Like the layers of an onion. This counts generally for all components. Lets start with the clothing. Footwear is most important, don't spare on that. This also depends on your terrain. For Canada, I would go for Baffin (Hudson and a pair of rubber boots or these classic Canadians with the lower rubber part and leather upper part), Meindl or Lowa. There you need excellent footwear for winter. For tropical climate lighter sport shoes and a pair of good rubber boots (always with removable felt inlay). In an urban setup you need more light and stealthy, but anti-slip sport shoes which are also suitable for climbing. In case of snakes, you would also need something to protect your shins (you may improvise with PET or some layers of newspaper.) At least two pairs of good(!), expensive long wool socks (not more than 5% sythetics!) For underwear cotton, the next layer would be long johns and a turtleneck: best is sheep or alpaka (!$) wool, that keeps you warm even when it is wet. You need this also in a desert-setup where the nights are cold, also in winter-California, less in the rainforest. The next layer would be sturdy, maybe a cotton working overall or functional military quality fabric. Cargos are very practical. Don't go for jeans or pure synthetic materials. Leather is robust but also soaks. Waxed deerskin ($) or oiled cotton or cord (robust, the ones used by traditional carpenters) may be also an option. Jeans are very uncomfortable when wet and synthetics are mostly not fireproof and may melt into your body. Cotton just glows and can be put out quickly. Then a wool marine or good fleece, Thinsulate sweater (more lightwight). The sweater shall be windproof as well. A fishing vest with many pockets. A jacket (for mountain and northern climate). I would go for Xzet or Drizabone riding wax jackets with the shoulder cover. These are nearly indistructable wind & waterproof and have turn-up collar with a snap. The jacket shall be not too short, can be also a short coat. That protects your bottom if you sit on wet or cold ground. The zipper must be covered against windblow and the cover must have buttons or snaps, not only velcro. Zippers might break and are hard to replace in this case (one may install self-carved buttons to improvise). The long riding coats with leg-straps are really good for motorbike or bike use, as they keep your legs dry. In an Urban setup I would go for a lighter jacket for quicker moves. Maybe a slightly lined non-rustling nylon or cordura jacket with a hood. Then you need a good hat to keep the rain away from your face, neck and for insect & sun protection. A scout rabbit-felt (well spray-impregnated on top!), leather or wax-cotton hat is fine. An impregnated fishing hat is more lightwight and less bulky, but has less sun and rain protection - will do as well. The scout felt hat can be also soaked with water for cooling. It is a means of taste and setup matter. You will also need a (wind-proof Thinsulate!) beanie to keep your head warm (also at night). One looses most energy from the head and by breathing in cold air. Also good in winter (or for uban cases) is a beanie and a baseball cap on top (if you have a hooded (rain-) jacket). A balaclava is lightwight and practical in winter and uban cases. A face insect net is a must for swampy areas, esp. when malaria is a topic. Those mosquitos can make one's life a hell and may drive one crazy. Then you will also need a good teflon coated rainpants with zippers, velcro and rubberband at the legs to slip in quickly with the boots on. Good would be also a hook to link into the shoelaces or gaiters for snowy areas. The sturdy rainpants have this integrated square raster garment pattern. One shall make some extra zig-zag stitchery with sturdy twine in the crotch area to reinforce these further and to prevent ripping when working on the ground, reseal the seam with spray or a little silicone. One pair of Thinsulate gloves (for normal winter) and the Würth anti-cut fine mechanics gloves (link on page 1 -these are a must! -nearly indestructable -lasted 2 years on garden and heavy demolition work. Normal leather gloves: 2-3 weeks or less. And you can pick up a needle with these, as they have a gecko-like grip pattern. And just cause very low to no sweating, compared to other rubber gloves. I had also no blisters despite of heavy shovel work!). At last you also take one of these sturdy lightwight (!) rain ponchos with the integrated bag and elastic band to buckle on (old us army stuff -not the heavy new ones) -big enough to cover your backpack or to be used as a tent-replacement. In northern Canada or Alaska one would also need special (e.g. fur clothes: hooded mantle, fist gloves and overshoes) winter gear.
The rule is always get out of the warm layers before sweating and get warm or anti wind or rain layers on before getting cold or wet. Then you are always comfortable, which is most important. High, wet grass: rainpants on. Your appearence should neither be military or combat style, nor like an academic neo-naturalist who is an easy victim (jack wolfskin, north face...), nor like a criminal tramp.
