I wear stuff that fits well and is flattering for my physique, but at 270lbs. lean it takes a lot of searching to find stuff like that. A local western wear store has a house brand of polyester polos that fit me incredibly well; other than that all I wear in public is XL Under Armour Tech t-shirts.
I have no problem making a grocery trip after the gym in a stringer tank top and gym shorts but I don't go out intentionally wearing stuff like that to get attention. Once you hit ~250lbs. lean, you're likely to get looks and comments no matter what you wear unless it's excessively baggy and people can't see your shape. My girlfriend likes to walk behind me in public to see people's reactions to me; I rarely notice them any more. Our perception as bodybuilders get very skewed - even in full blown offseason at say 12-14% body fat we're still amazing to the general public, even though many of us would consider that a bad look.
My biggest clothing issue now is jeans / dress pants. Lucky has one line of jeans that my thighs can just barely still squeeze in to, but I suspect they won't after this year. I get my khakis made custom, which isn't that expensive depending on where you go and is totally worth it to look good and be comfortable.
Getting a new wardrobe is one of many things people don't think about when they want to get really big. I even had to go up a size in boots this year.