Giovanni does bespoke work. He is on 17th ave at 37th street SE in the SE corner. I have never had a shirt made from him, but he told me he is one of 6 bespoke tailors in Canada. His shirts would certainly be over the $100 mark. His suits start at $900.
I have had pretty good experiences buying shirts tailor made online.
www.indochino.com has a great measuring system. Basically you can measure yourself or get your girlfriend to measure you. They have instructional videos for each measurement you need. However, their shirts run at $99.
I do not recommend Indochio suits. You can get them for $360 or whatever, but they are a $360 suit. I guess if that is what you're looking for, then thats ok, but saving a bit up and getting a higher quailty suit is probably a better idea IMO. Mostly because of the difficulty of getting the jacket correct and the fact that the quality of the jacket is not the best. Very hard to do over the internet. Pants on the other hand are pretty simple. So are shirts if you have the right measurements.
I normally just take my measurements from indochino and input them to
www.blank-label.com Blank Label has a ton of shirt options for you to choose from. If you just go with the basics, depending on fabric you choose, it will be $45 or $55 plus shipping.
Quality is getting better. I've had two shipments from them. The first shipment had lots of loose threads, and a couple places where they missed stitches. Also, on their older shirts, they didn't have removable collar stays.
On the second batch I got from them, there were hardly any lose threads, the material seemed fine, stitching was decent, they added removable collar stays, and they made the shirts to my measurements. So I am happy with them and will buy again.
Blank Label aslo keeps changing their fabrics, so I don't actually own any of the ones they currently have on the site. If you want, I could take some pics of the shirts I do have and send them to you. Also, fabric information is not avaliable on BL, which is a bummer. You need to email them if you want thread counts, weave, etc for a specific fabric.
Hope that helps, let me know if you have any other questions.