so i guess this has turned into 'stuff i really love.'
anyway...
first off is my ll bean katahdin boots. i bought these with a gift certificate my grandmother gave me like 4 years ago, and i fucking love them. i wear my shoes really, really hard, and wear these 3-4x a week in the winter, and they've held up great. probably will need to go in for a resole soon, but since getting these i've never even really considered getting another workbootish type boot.
some pictures:

next is probably my j crew down jacket. i bought this a couple years ago for like 70% off, and it's the perfect knock around winter jacket. it's torn to shit and has a bunch of paint stains on the back and sides, but i love it for when it's 2 am and i need to walk the dog.
stock pic:

i also have a fleece sweatshirt from j crew that i fucking love. its dark grey, a thick fleece, about 4 years old. it's been worn and washed dozens of times and has held up great. i wear it constantly in the winter and it's the perfect weight for layering. it's also made in canada by CYC - has all the deets of W+H and spruce stuff i've had - and i got it for like $25.
finally, i have a boo oxford from one of the first seasons - retail was like $160 i think - that has been torn, tailored, worn, stained and washed. at this point it fits all kinds of strange and needs to be resewn, and has a bunch of paint stains from a shitty under 21 club some girl dragged me to, and even though i've replaced it with other shirts, i'll never get rid of it.