Yeah, I think you have to have the original TG armor to be able to get the Guildmaster's Armor. I know you at least have to have the TG armor and upgrade one of the pieces to meet the requirements.
According to every source I know of, yes, you must keep the original TG armor in order to upgrade/exchange it for the better stuff you will be given if you continue with that questline. If you sell it or lose it you're out of luck.
one of my many mistakes my first time through... figured I didn't need it. DAMN! lol From now on I keep that first set.
However if you search around the beds you may find gear lying around. I found a pair of boots last night when looking through all the chests. The boots were tucked away and didn't have "steal" on them so I took them.
Try that before you start all over. check the thieves guild training/bed area for those boots.