He Who Brings The Coffee has a new pair of jeans. They’re this sort: 
You know, the ones with the holes in them. May I remind you of the fact that I haven’t got an ounce of discernment in me when it comes to differentiating between something that’s the height of fashion and something that your granda would wear.
“D’you like my new jeans?” asked He Who Brings The Coffee, striking a little catwalk pose. I looked nervously at them, the usual feeling of dread setting in. The options were: (a) he’d got a new pair of super-trendy jeans and was genuinely very proud of them, or (b) he was planning on doing some gardening and was therefore wearing an old, scruffy pair of jeans and taking a hand out of me. Either one of these could very possibly be true, as far as I was concerned. Hence my dilemma. If I said “Yeah, they’re lovely, where did you get them?” and Situation (b) turned out to be the case, he would roar with laughter. If I said “Those have seen better days, haven’t they?” and Situation (a) turned out to be true, he would be horribly offended.
Either way, there would be no doubt that I am thick as champ when it comes to clothing-related issues. My palms sweating, I decided to go for secret answer (c), the say-what-you see option. “They have holes in them,” I said quite simply.
He looked impatiently at me, and I panicked. Now desperate, I took a stab in the dark. “They’re… really cool.”
He looked pleased, and wandered off. I slumped over my desk, feeling drained. “Zed,” I asked carefully, as she approached me with an amused grin on her face, “Are those new jeans or old jeans?”. She patted my arm reassuringly. “You got it right, pet.”
Relief. Pure, unadulterated relief. People need to please stop asking me what I think about their clothes. Chances are, the answer will be “I don’t!”.
Coffee Helps: The Decaf Years 
Hahahaha!
Can’t imagine him wearing those.
Is he a closet Bros fan? Does he have bottle tops on his shoes?
OR, is he having a mid-life crisis?
Don’t tell him I said that. He will kill me :)
That reminds me of a time when I was increadibly insensitive and got into trouble with a friend of me fella’s.
He’d just forked out €120 for a brand new shirt with paint sploshed all over it and I told him he was a complete gobshite.
Bless you for your tactfulness. Sometimes people blatently ask to be insulted sometimes though. It’s not my fault!
Billy – I quietly asked Zed if she thought that might be a possibility, and she just said “shhhh!” in a panicky sort of way, glancing nervously over her shoulder.
Sheppitsgal – ha ha! Doubtful. I really think it’s the mid-life crisis thing. It could have been so much worse than a pair of jeans.
K8 – I live in fear of unintentionally offending someone. Maybe I should just go for it with the honesty. I like your style!