So, at this very moment I have a few lower-end suits, but do want to invest in either a nice blue or light-gray plaid suit. I'm not exactly sure what I should expect to spend, but I can say I want to keep it under $1,000. Off the rack from Brooks Brothers or something, then getting it tailored is what I have thought of at this point. Thanks for the help guys!
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I'd steer you to trying on the Brooks Brothers Fitzgerald cut as a good starting place. I've been hearing really good things about made to measure Samuelsohn suits around here lately. They will most likely be my next suit and it's ballpark your price range. I'd also steer you to looking at suitsupply.com for some browsing.