I have my clothing choices for Philmont, but I wanted to run it by you guys to see what you think.
To be worn on the trail:
-Columbia Tamiamiâ„¢ II LS Shirt – Longsleeve button-down shirt similar to a Cloudveil Classic Cool: Link to Shirt
-REI Sahara convertible nylon pants
-Synthetic Boxer Briefs: one pair Under Armor
-DeFeet Woolie Boolie Merino wool socks
-Colombia Ice Cap with neck drape
-Brooks Cascadia 7 Trail Runners
Additional Layers:
-Stoic Hadron Down Cardigan (Insulating Layer)
-Marmot PreCip Rain Jacket (also serves as windshirt/windbreaker)
-DriDucks RainPants
-Mountain Hardwear Dome Perignon fleece hat
Sleep Clothes:
-T-Shirt
-REI Medium Weight wool hiking socks
Extra clothes carried:
-Starter Polyester short-sleeve wicking T-Shirt
-Starter nylon boxer briefs
-DeFeet Woolie Boolie Merino wool socks
-Colombia Nylon shorts
Does this seem like a reasonable list? Do I need the third pair of socks just for sleeping, or can I just rotate my other two pairs daily and sleep in them too?

