Secondhand, pants, etc.

Hi everyone. I'm a relatively new hire and trying to build out my work clothes set. Had a few questions.
Firstly, if I'm looking to save, what articles of clothing are good thrifting finds and which are shit? I ask this because I found a pair of black captoe Oxfords in spectacular condition, as well as a belt and shirt, but sports jackets and the like aren't so easy to find; a lot are either too broken in by their previous owners or have some sort of damage.

Secondly, in terms of a simple pants-shirt combo, what patterns, colors, and materials are acceptable? Right now I have charcoal, navy, dark blue, and black dress pants. I was thinking of getting pinstripes but I don't know if they're acceptable on their own, and have seen dark brown widely available.

Finally, I have a relatively misshapen build. My arms are pretty short and my shoulders are narrow, but I have a long torso and wide neck so smaller-sized shirts don't fit well. I already have a tailored suit that fits me well and I've gotten it adjusted as time goes on, but what about shirts and extra suits? Do I just buy off-the-rack and take them to a tailor? Have seen SE Asia as an affordable option for new suits, so if anyone has a specific name they are attached to let me know. The same goes for tailors in NY; I've gone to the same one in Midtown for a while but was using one uptown when I was a broke student. 

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Thanks. Which brands do custom sizing? Also, any advice on patterns in jackets or pants? My bank is relatively lax on analysts but I like to keep it toned down.

 
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