To the OP: Can you increase your budget? A cheap suit will look like a cheap suit = pissing away your money. A quality jacket or blazer would start at a minimum of $600 - something from Boss or similar. Perhaps get by and save on a pair of pants?... I'm not sure about that shizer Korry's spouts off on, but Harry Rosen's stuff is 'good' and sold by other quality men's clothiers (including Korry's). At Harry Rosen's, JP Tilford (aka Samuelsohn) or Coppley are where you'd start, I'd think. I hope you fit off-the-rack as well or are at least close...
If you're an Adonis, then you can get buy in something from Value Village as your muscles will ripple through and take care of you... Keep in mind that will only work with some women and not with others and definitely not against your male peers.
The best example I can find are the Rogers commercials... They 'loser' dude always looks like a chump, one step out of his FutureShop salesman career, in comparison to the guy who has the nice gear and gets it done in business and with the ladies. The difference in fashion/quality is noticeable. I guy will respect another guy who's starting off his wardrobe on the right foot.
Stop visiting the escorts and/or the bar for a bit and make the quality clothing purchase happen! Set up an ongoing budget, make a 'relationship' with your tailor or advisor and work towards it buying investment pieces.
For me, I've shopped around in various places, but found my best experience with one guy in particular at Harry Rosen. The guy makes an effort, hussles and works for me.
Be a pimp and do the right thing.