Help getting started in vintage -- Chicago

[vxt22]

Hey chaps. I'm new here, and just starting out trying to wear vintage clothing. I live in Chicago, and was wondering where to get started. I've bought myself a nice fedora that I love, and plan to buy another cheaper one for every day wear, as well as a newsboy cap. I'm a college student so I can't drop hundreds of dollars on rare dated vintage suits.
So perhaps what I'm looking for in an answer is what sorts of clothing make up a working man's wardrobe from the late 1920s early '30s era. Were do I find decent wool or tweed or (another suitable material?) trousers that are like what was worn? What other pieces should I be looking for? Vests I suppose? Or overalls. And a trenchcoat of some sort. And I think it'd be a bit awkward to just wear a normal t-shirt under all this stuff... so what should I be looking for in that department?
I guess I'm just a bit overwhelmed. Concisely, what pieces should I be looking for? Also, where in Chicagoland should I look for this stuff, including a three piece double breasted suit? Just need a bit of a push to get going I think.

Thanks for any help!!! There sure are some cool cats here.

 

[ortega76]

Good to see more folks from the City of Big Shoulders. Welcome to the Lounge!

 

[Baron Kurtz]

Night and Day vintage are very good. Reasonably priced, also.

There's always the standard "check the thrift shops" answer.

bk

 

[Tomasso]

All the vintage shops peruse the Brown Elephant.