The issues I think you are going to run into are pants sizes. When I was my heaviest at 267 and a 44 waist size. I could find jeans all day long to shove my Glock 23 in my pocket behind my fat leather wallet (prevented printing). Now I'm back down to a size 36 and I need suspenders to properly wear my 44s and it's gotten on the verge of ridiculousness how they fit and look.
My suit pants oddly enough are great for carrying my Rossi 462, SP101, XDS .45, and on occassion my Glock 23. I've bought about a half dozen pairs from the local thrift store (I've seen folks driving hummers shop there and I at least drop off the clothes I find in the storage units I buy) and they are by and far the best for concealed carry. So much that I now typically wear a pair with a machine washable dress shirt and sports jacket (thrift store bought for eight bucks or less). It's an odd look for a 29 year old but no one seems to really give me a bother which is great because it also lets me use my shoulder holster and carry a large semi automatic as well.
Do yourself a favor, clear out your closet for clothes that don't fit, visit the local thrift store (Goodwill) and do some pants shopping after you drop off your clothes. It might feel weird to have money and be buying from Goodwill but you can balance your karma with the fact you are also helping create jobs for the folks who work there as well. Just my suggestion.