Adventurers' Clothing, in "Stoneflage" (Mottled grey that blends in well with shadows and stone).
Broad leather girdle with pockets, two belt pouches, and sheaths for his longknife & handaxe, as well as a Healer's Kit in the back, as a buttpack.
Manriki-Gusari (around waist, under the girdle).
Cloak & Boots of Elvenkind.
Heward's Handy Haversack with a Quiver of Ehlonna on each side.
Leather Gauntlets.
Claws.
Buckler on the left hand (in which he carries the bow).
Dastana (Bracers).
Mithril mail hauberk (shirt) with the ability to disguide itself (matches stoneflage clothing).
Vest of Escape (under clothing).
Extra wool cap, cloak liner, glove liners, mittens, socks & underwear, along with a change of clothes in the pack, and a suit of Snow-Camo Cold Weather Clothing in the Warhorse's saddlebags. Bandannas and a Shemagh (long scarf wrapped around the head & neck by desert peoples) are added to the mix, as needed, or stuffed into pockets and pack, when not.
At lower levels, here's my advice on clothes (from "The Ten Essential of Survival, D&D Style" Copyright 2004 by SteveC. Licensed for individual use.):
Clothing: PCs are given a lot of liberty, here, by the description of the standard "Adventurer's Outfit" in the PHB. They can freely specify that they have a cloak, jacket, scarf, hat or cap, gloves, socks, and (depending upon your GM) things like handkerchiefs or bandannas, a poncho, a liner for cloaks/jacket/poncho, etc. PCs should take some care in specifying what they have, with an eye towards survival.
Personally, I can't see taking anything but the Adventurer's Clothing, for normal use. The other outfits have their uses, but for general adventuring, this one is properly titled. I also prefer cloaks with hoods to jackets and hats, but your tastes may vary. In any case, add a warm woolen cap/hat that covers the ears and neck, perhaps a scarf, leather gloves, warm, thick socks, a button-in cloak liner for cold weather, and some underthings, as well as some bandannas.
For more on the cloak, see Shelter, below. Obviously, the cap, scarf, gloves, and liner will aid in making cooler weather more tolerable. The bandannas will serve other uses, as well. Straining impurities from water, acting as a sling for a broken arm, used as a signal flag on the end of a pole, as a tie off, tied around the mouth and nose in dusty conditions, etc. In fact, they are so useful that the Boy Scouts of America has made one a part of the scouting uniform!
Even such things as boot laces have their places in survival kits. In dire straits (where a lot of adventurers seem to spend their time), a shelter may mean the difference between life and death. Three saplings, tied together at the top with boot laces, and wrapped in cloaks tied with bandannas, or covered in large sheets of tree bark may someday save a PC. Other things can also be worked in... See Weapons, below!
In addition, don't forget to take an extra suit of clothes along. How many times have you seen a PC fireballed, and their gear burned, or had one fall into an acid trap, and lose their equipment? An extra suit of clothes in the saddlebags usually solves this difficulty, and it doesn't even weigh you down!
Also, when going into cold weather, knowingly, always take along a suit of Cold Weather Clothing. It adds to the save versus cold weather damage, and weighs even less than the usual adventurer's clothes! Note here that one suit of clothing is given to the PC, free, at first level, and doesn't count against their encumbrance, either. So there is no excuse for not having this essential!
It may also be worth noting that, when in cold weather without the proper gear, and your PCs are unable to stop for some reason (such as ardent pursuit!), that you can cut two arm- and leg-holes in your sleeping bag and wear it, to keep warm and dry! If you do this ahead of time, be sure to include storm flaps and buttons, so that it can be used for its original purpose, again, without cold, chilly drafts bothering you while you're trying to sleep! The exposed arms and legs can be covered with sheets of birch bark (if available), or wrapped in blankets, or other such materials.
Shelter: In D&D, the only type of shelter commonly available to you is the tent... Yep, that's it! The old equipment list is pretty bare... but I bet we can do it one better! Tents are fine, and all, but at 20 pounds, not something you want to carry with you, unless your armor already puts you into Medium Encumbrance! The bedroll/sleeping bag and blankets may also fall into this category. Adventurers should always have a bedroll (which includes the light blanket), as well as a heavier winter blanket... You can always use it to sleep on top of, on hard ground.
An easier way to carry your shelter around with you is the oilskin leather raincloak. This is the D&D version of the US (and German, and...) Military rain poncho. A leather cloak, with hood, which has been treated with oil to make it waterproof. Buttons down one side, and button-holes along the other, allow it to be closed up, tight, in bad weather. A drawstring in the hood, and another at the waist, help keep the storm winds out. An extended storm flap, with an additional row of buttons, also help. You might also like leg straps, on your version.
In addition, metal grommets along the outsides allow the cloak to be staked down, in high winds, and an additional row of buttons along the inside allow that extra liner to be buttoned in, to help keep you warmer with an extra layer of insulation. Best of all, whenever two of these cloaks are buttoned together, face-to-face, they form a makeshift tent!
Want to wear it while leaving your hands free? Two button-up, strom-flapped slits along the front can act as armholes, if you like. Just make sure that the armholes are covered by the storm flaps, so that the rain doesn't run down, into your cloak when it's buttoned up!
Since the Adventurer's Clothing allows you a lot of leeway on the type of gear it provides, see if your GM will let your party take these. Note here, however, that there's a major difference in size between the Small Gnome/Halfling version and the Medium Dwarf/Elf/Half-Orc/Human version!
Even if you prefer a coat or jacket to a cloak or poncho, oilskin leather is a pretty good solution. You won't be able to use it as a tent, however.
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