Seconding Modcloth! They have a lot of cute, classic styles for (I think) good prices. I've gotten a few dresses from there (ranging from $35-$55), and I've worn them all a lot, so I think the value is fantastic. Plus, they almost always have nice things in their sale section. (Every single time I wear the Coach Tour or Soda Fountain dress, I get compliments, so hooray for that!)
If you're looking to spend a moderate amount on one or two pieces ($65-$100), Pin Up Girl Clothing would be great, too. (pinupgirlclothing.com) They have TONS of vintage-inspired dresses named after bombshell actresses, and the quality is really good, too. They've got some really beautiful dresses.
Also, picking and choosing separates from "big box" clothing stores can work really well - cardigans and blouses from Old Navy and Target, skirts from the Gap, etc. I basically haunt the sales racks and scoop up last season's stuff. Are you close to any outlet malls? My favorite pair of jeans (ever) I got for dirt cheap from an outlet.
(Also also - Hot Topic has some cute retro-inspired dresses, and JC Penney had some classic-looking blouses for a good price).
So excited for you, happy shopping!
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