Good work, man...
I began my quest into proper clothing in a similar manner. I lost about 25 pounds during the winter of 2011-12, and had to buy an almost new wardrobe. I've always been a thrifter, but have greatly expanded the upper-end of my wardrobe. I used to be a shorts and t-shirt guy, now at least I'm wearing button-up shirts, pants and shoes most of the time (Aloha Fridays beingthe exception!).
I'll try to keep it short. (Click to show)
In an effort to replace my old wide body wardrobe, I ended up here (like so many of us) while google searching men's clothing and got sucked into the need to learn about how clothes should look and fit. I had already dipped my toe into the thrift waters when I purchased this cheap assed, horribly fitting cord coat, complete with upper denture in the inner pocket!
I was still working on the fine art of posing to show my new clothes to best advantage. The hair was still a work in progress as well.
With the tough love that you can only get from the WAYWRN thread, I gradually learned what fit me and looked right. Spoo was one of my biggest cheerleaders but there were several others who helped as well and they ALL called it like they saw it. I highly recommend it to anyone who is trying to learn like I did but be advised, one needs to accept the criticism constructively or people will tire of one's defensive explanations of why people shouldn't be so harsh and they will stop helping.
I found a local alterations lady who eventually accepted my instructions for fitting my finds in a way that other men usually don't. She's eastern European so after the first efforts on an H. Freeman & Sons, she realized that I was going for a more tailored, continental fit and actually had a clue. I tipped well on that suit and several other smaller projects.
I found that Brooksgate POW at what would become my 'honeypot' for BB suits. It was my first big find other than the H. Freeman that I happen to like as well. I took it to her and we altered the hell out of it and she barely charged me for the work! I wore it to work one day with the intention of finding a nice location to set up my (thrifted!) camera and tripod.
It was late afternoon and the place was closed. The sun was lower in the sky and I started taking pics. When I saw that one in the display, I turned off the camera, folded the tripod and called it a day.
I posted it up that night in WAYWRN and got a pretty favorable response.
That's about it!