What do you wear?

Also in the PNW. My Summer gear is very similar to yours, only real difference being a Power Stretch pullover instead of a vest, I just find it nice to sleep in. I'm switching to a long sleeve nylon button-up (Columbia "Bahama" or something like that) instead of a short sleeve to help deal with bugs. Generally don't carry gloves in the summer, and I don't use rain pants any time of year.

Shoulder season- the only difference from my summer gear being a Stoic synthetic hooded puffy in place of the pullover, and light fleece mits. I run way too hot for long johns.

Winter- Add a fleece vest and long johns. I usually wear my normal socks but with insulated boots if its really cold, but thats not often. I also bring TurtleFur neck gaiter, the warmth to weight ratio is amazing.

Unless I'm mountaineering or bushwacking, I use the same Golite 2.5 layer rain shell year round.

By the way, I just found awesome "thinny-thin" nylon socks at Target for 8.99/3 pairs. I've used them every day for a few weeks now and love em.

Edit- rain pants.

I hike very hot, sleep cold, so summer/shoulder seasons are the same.

Summer/warm weather:
Trail; Poly shirt or Merino wool long sleeve, 5" shorts, Wind shirt, Merino wool boxer briefs and socks.
Insulation; Wind pants, 12oz down hoody.
Accessories; Sun runner cap with neck coverage, DGG gaiters, trail runners.
Rain; DriDucks jacket, Wind pants.

Winter:
I'm in the desert in the winter time so same clothing.

Edit: Summer Sierras and Death Valley winters.

Really hot > 100F:
Rail Riders Eco-mesh shirt and pants, Ex-officio boxer shorts. Tilley LT4 hat. Light poly low top socks. The lightest running shoes I can find.
Accessories/other: Ex UL Jacket or vest (sometimes hike from desert to alpine), Houdini Wind Shirt, Poncho, glove liners if at high altitude.

Not so hot/So Cal Shoulder:
Very light running shorts, no liner, no briefs. Light merino/poly long sleeve shirt. Usually no hat. Light poly or merino or blend low top socks. The lightest running shoes I can find.
Accessories/other: Same as above except maybe a eVent baseball cap if it is going to rain a lot.

Winter/Snow:
Capilene 2 top, Some sort of Schoeller pants, often an eVent hat with ear flaps, lined with primaloft. Sock liners, Rocky GoreTex Socks, Mid weight wool socks. Size up on shoes (Salomon XA comps breathable). OR Verglas Gaiters.
Accessories: R1 Hoodie, Houdini Windshirt, Capilene 2 bottoms (sometimes hike in them alone with UL running shorts), poncho, sometimes WPB jacket, sometimes rain skirt, Ex UL down midlayer, NB Fugu, Mount Bell down innder pants, 2 or 3 pair glove liners, eVent Mitts, sometimes insulated gloves, some sort of beanie/bacalava may be more than one, extra wool socks.

Every trip is different so I often mix and match. Sometimes in heavy cactus country I will wear Salomon XA comps breathable. Sometimes in cooler weather with gastly amounts of sand I will wear GTX Salomon XA comps to keep the sand and dirt out. Once in a while dirty girl gaiters or eVent shorty gaiters… usually only once or twice a year.

Once in a while I will hike in some sort of long sleeve nylon shirt and/or pants because my wife did the laundry and I cannot figure where she hid/placed the Rail Rider stuff even though I have 4 sets of each. I have many Columbia, REI, Ex-officio shirts and pants (they are an easy Xmas gift for someone who doesn't want gifts). But usually use the Rail Rider Eco-mesh. Never, ever use convertible pants because I just hate them. Because I get to hike a lot, almost every weekend there are smelly clothes in the hamper and my wife won't wash them unless they start to stink up the house. Plus she isn't going to do a special wash for Merino, and I once caught her trying to throw 3 down jackets and a pair down pants into the washer… luckily I caught her just in time :)

base (short or long sleeve depending in season)
optional R1 copy/fleece depending on season
windshirt/vest or softshell (depending on season and the climb)
optional rain jacket (UL for nicer seasons, a bit heavier for harsher ones)
puffy (down, synth weight depending on the season)

optional long underwear depending on seasons
wind or softshell shorts/pants (depending on season and climbs)
optional rain paints (for the real "gnarl")
optional fleece or puffy pants (for the real "gnarl")

thats it … the weight and particular items varies … but the concept is the same

keep cool when moving … be effing warm whenever you stop

if you are intelligent you can use many similar items in summer and winter …. ive used some of the same items climbing from 70F to -20F

Summer:
synthetic t shirt
zip off pants (zipped off)
sun hat
buff bandanna

Fall / Spring:
long sleeve sun shirt
synthetic t shirt
zip off pants (not zipped off)
sun hat
buff bandanna

Winter:
synthetic long sleeve shirt
synthetic long underwear
runners hat
softshell pants
softshell jacket
merino wool buff bandanna
super thin glove liners
fleece gloves
mitten shells

When I'm around camp:
I'll add a puffy jacket and paints as needed for the season and weather. In winter I'll add down booties and a heavier puffy jacket

It's not rigid by any means, but here's my general clothing systems for my seasons.

Warm/dry weather:
worn:
running shorts (Patagonia Nine Trails) or thin soft shell pants (Patagonia Rock Guide)
synthetic boxer briefs
synthetic t-shirt (Patagonia polarized shirt) or long sleeve sun shirt
synthetic micro-crew injinji socks

packed (wear as needed while hiking or in camp):
Patagonia houdini windshirt
Patagonia UL down shirt or down sweater vest
thin synthetic glove liners
thin synthetic beanie
maybe a pair of silk long johns and top
thin sleeping socks

cold/wet weather:
worn:
same basic worn clothes, maybe swap out synthetic socks for wool injinjis.
ID eVent gaiters

packed (wear as needed while hiking or in camp):
windshirt or ID eVent rain jacket (never bring both)
Montbell Dynamo wind pants or Golite Tumalo (sp?) pants (ditto above)
Ibex Indie top (like BPL merino hoody)
Patagonia UL down shirt or down sweater (if really cold, add down sweater vest too) or go with syn if expecting soggy/wet
swap out beanie for merino balclava
replace glove liner with 1-2 pairs of thin gloves (OR omni, mid-weight merino, etc.)
silk long johns (or montbell UL down pants if expecting really cold)
thin sleeping socks and/or Goosefeet down socks
if needed, pack/wear goretex socks and/or eVent mitten shells

Most of my hiking is done along the central CA coast and nearby mountains, so weather forecasts are pretty stable. I can head out with a reasonable expectation that the weather will follow the forecast. Depending on season, hiking can be in 100+* heat and sun at its hottest, or cold rain/snow in the teens at its coldest, and of course, the whole range in between. When in doubt, I err towards a kit prepared for a little colder/wetter than forecast.

Southern Rockies in the summer, desert/California in winter:

Base (NTS):
Capilene 1 or 2 ss (oops, add a Smartwool lightweight nts that needs replacing due to large holes)

Shirt:
(Rough trail) Mountain Hardware eXtend zip-T (snag-resistant, discontinued) or (Good Trail) a second LS Capilene zipT.

Pants
Patagonia Rock Guides or their GII pants (will be trying some Westcomb made with Schoeller fabric for snowsports this winter). I do not wear shorts unless there's dedicated swimming.

Fleece:
Patagonia R1 or R2 as needed (need a replacement for my Patagonia LW R4 for snowsports as it's warm enough, just do not like falling snow catching on the soft fleecy face)

Shell:
Patagonia Houdini (wind-stealthy alpha green), TNF anorak if rain unlikely, Patagonia Jetstream H2NO w/stretch (dedicated 3-season) or (snow on the ground) a Marmot Oracle (2004 version with stretch) – love its 'all in one' zip-pit/hand-pocket design, despite it's heaviness.

Hat:
Ball cap and warm hat (unless my fleece is a hoody), plus a buff

Feet:
TNF Hedgehog trailrunners w/REI synthetic running socks mostly but I have some Patagonia trailrunners (lots of ventilation) I wear with low merino wool socks when it's warm.

Down:
If needed, add a FF Hyperion vest in Epic or Pata down sweater hoody on top of it all. Might have gone too far on the last item.

I've gone through a lot of clothing and this is what is left.

ADD: Once I've finalized my snow clothing, it's time to look at some aquatic almost-canyoneering stuff for a Sedona trip next year.

Summer in the sierra, spring fall winter in CA coastal or desert climate

I Switch things up depending on variables between these items

Synthetic boxers
Gym shorts
Heavyweight long john pants
Midweight longsleeve shirt
Sleeveless lightweight Tee
Zip off convertible pants
Lightweight wool pants
Thick coushined wool socks 3 pair

Fleece gloves
Fleece beanie
Fleece neck gaiter
Down parka

Wind parka
Rain poncho

Merrel ventilators (love em)

"Sierra and the Cascades in the summer/fall"

Base:

Arc'teryx Motus LS "T"

Shirt:
Montbell Ex Light Down Shirt

Pants
Montane Terras and Patagonia Classic Boxer Briefs underneath

Insulation:
Montbell UL Down Parka

Windshirt and windpants:
Montbell Tachyon and UL Windpants

Shell:
O2 Rainshield Parka

Hat:
OR legionnaire style ball cap and MH Transition Featherweight Beanie

Feet:
Inov8 Roclite 370's with Injinji Performance socks NTS and Coolmax liners over them.

Hands: REI Polarguard Windpro gloves with OR Goretex lobster style WPB gloves for mid September on.

I don't do winter trips anymore, and my Cascades dayhiking clothing is a whole different list. Some other time.

(Brand names omitted to halt GearBuyer)

Desert:
LS convertible light-colored Synthetic Shirt
Convertible pants
Cotton or synthetic boxer briefs
UL Rain Jacket or Windshirt if needed
Light fleece, Down, or synthetic puffy if needed

3 Season Midwest and Appalachia:
SS Merino Wool shirt and/or LS convertible synthetic shirt
Eco Mesh pants (permethrin treated for ticks and chiggers)
Synthetic boxer briefs
Down or synthetic puffy if needed
UL Rain Jacket

Alaska:
SS Merino wool shirt and LS convertible synthetic shirt
Convertible pants (usually worn as shorts)
Rain pants
Synthetic boxer briefs
Synthetic long john bottoms as needed
Fleece midlayer as needed
Synthetic puffy and down vest if needed
Expensive eVent rain jacket

Winter:
Whatever keeps me warm and dry. Still trying to figure out what works for me. Not all of it is considered UL but that does not matter as much when the mercury drops.