Jos A Bank is fine for some pieces, but is definitely lower-middle end for suits.
I'd get a personal shopper at Nordstrom. Sounds extravagant, I know, but it actually really isn't: free service, awesome advice, and they can put together a great outfit (or set of outfits) on whatever budget you specify. My DH did this when he needed to overhaul his work wardrobe a few years ago and was thrilled.
Start by looking online at Brooks Brothers, Nordstrom, Jos A Bank (for comparison) just to get some idea of prices, so that you can plan a budget.