Steve,
For starters, walk into any JCrew store and ask to speak with a personal shopper. It's a free service that all of their stores offer and probably a good starting point for a wardrobe update. Their styles are classic yet modern and of good quality. The clothes do make the man...
Men's Clothing - Men's Underwear, Dress Shirts, Shorts, Ties, Jeans, Boxer Briefs, & More - J.Crew