I have close friends who would call my bags and wallets ugly in a joking way, not sure if that's their honest opinion since we do have pretty different styles. I'm not THAT offended because we're close enough and we jokingly insult one another all the time lol.
One time, though, after seeing my new wallet (while we were shopping together), one of my friends ran into the store from which I got the wallet, found it, and announced the price of my wallet to our group of friends (and in my presence, like 'hey your wallet was $xxx, right?). I was mortified! I mean I don't mind my friends knowing how much I paid for my wallet but for some reason what she did just annoyed me so much, it even felt obscene and distasteful :x
Another time, my other friend who previously insulted my new wallet (that same wallet) and said she didn't like the brand, etc (albeit jokingly) showed up two weeks later with her new wallet from *gasps* THE SAME BRAND! So I asked 'oh I thought you didn't like the brand?' And she was all 'yeah but my mum bought a bunch of wallets from them and I had to pick one so I picked the least ugly one.' (I know right?) And then proceeded to say something along the lines of 'although our wallets are from the same brand yours is ugly but mine is not'. Can you imagine how many times I had to roll my eyes that day oh god.