I’m a shy person, so when I give a compliment to a stranger in person, it means something really struck me.

We’ve all been young, so I guess we’ve all had our chance to have the opinions and prejudices of youth :-). Eventually they may never get compliments at all - sigh.

Such an interesting thread! And I’ve honestly never considered that my compliment could potentially put people off of their clothing.

I compliment people, without any thought to age, but wouldn't under any circumstance ask where they bought an item. That would be strange to me, outside of this forum.
If people compliment me, I don't care about the age of the complimentor either. That said I'm generally more comfortable with compliments from women than men!

I compliment others without thinking about their age. I wouldn't ask where they got their clothes. Women of all ages, including young, have complimented me on my outfits. I don't worry about their ages.

This is interesting! Like many others, I compliment people regardless of their age, but wouldn't ever ask someone where they got something. My 21-year old and I share a very similar style aesthetic, so we compliment each other all the time, and I pass things along to them if they are too small for me or I just don't wear them enough.

Oh gee, I compliment people all the time no matter their age. It never crossed my mind someone could be offended. Learn something new everyday!.
I have made friends with my inquiries... I also ask if it was locally purchased as I live in a community with local businesses who appreciate the word of mouth recognition.

Funny story - about 15 years ago I was looking at Docs in Nordstrom when a teen next to me tried on a pair of white sandals. Without thinking, I said, "Oh, I have those and love them!" Without a word she took the shoes off and walked away. I had totally killed her interest in them. I still laugh thinking about it.

I pay compliments to strangers when something is really striking, and often to friends. I will occasionally ask where something was purchased, but it often turns out to be "Singapore" or "Zara five years ago."

I love a compliment on my own outfits (as you all know)!

I tend to notice what other people are wearing, and over the years I've tried to make more of an effort to offer compliments when the situation is right. Being in the South, it has never seemed a strange or forward thing to do, like striking up a conversation with a cashier. I'm just quiet so I didn't do it so much. I like receiving compliments myself, so when I find I'm admiring something internally, I express it if I can.

As far as receiving them, I tend to get a fair amount. I've also noticed that it's almost never on a single item. People tend to notice the outfit or general effect and want to say something but sometimes don't quite know how to express it. I can recognize this because years ago, when doing living history, I got some comments from visitors admiring my outfit. And in this case, it was because the clothing was historically accurate. There were many others there with more eye-catching (and costumey) outfits, but these people responded to the rightness of the look without even knowing the history. I think I recognize something similar now. When someone likes my outfit, sometimes they'll say "Nice dress!" - even though it's a skirt and top and cardigan. Or more generally "I love the way you look!"

I'm kind of rambling since I haven't experienced the feeling of either receiving dubious comments or feeling that I've given them! Although... There was the time a young 20-year-old or so just LOVED my SAS wedge loafers that I'd bought off ebay. I was wearing a tweed skirt and dance tights that honestly can look like compression stockings and the loafers look slightly... orthopedic to my eye. I was mostly wearing them since they were comfortable and I'd gone for a walk in them earlier. I'm still not quite sure what to think of that!

Ten days ago my 29 yo DD contacted me asking for a picture or link to my kitty shirt (Find below) because she'd seen someone with a similar shirt and became obsessed. Said we could have mother/daughter shirts, lol. Who knew? But mostly she wouldn't wear anything I wear.

Wow, what an interesting thing. I guess it never occurred to me how someone might take a "compliment" as the opposite of how it was intended. That said, I rarely if ever comment on random strangers.

I am 52 and I work in a k-12 public school building. All coworkers compliment one another and no one seems to take it the wrong way, regardless of age (early 20s to almost 70). Likewise, you can compliment a child up through about 5th grade and they will smile ear-to-ear for the rest of the day. But I never, EVER comment on the sartorial choices of middle school or high school students. They are so emotionally volatile that it isn't worth the trouble.

I am definitely a shoe person, though, and my room is across from a Middle School study hall room. When I am outdoors sometimes for a recess and have changed into boots, coworkers tell me that middle school girls have snuck into my room to try on my shoes. I am not offended, and they clearly must not think I have "grandma" style. I decidedly do not dress like a teenager, but all bets are off when it comes to shoes (except no stilettos. I just can't wear a very high heel, and I don't even find them visually appealing anymore).

Interesting thread, thanks for the discussion! I'll admit that I used to compliment people more back home (even though Brits aren't exactly known for polite small talk with strangers lol) but out here I don't really anymore - regardless of age. Partially because of the language barrier but also because I sometimes find folk staring, even without striking up conversation with them first. It would be nice to get compliments from others (& give them!) but the last 2 times I received comments here were actually from men (commenting on my red trousers looking 'festive' around Xmas time, etc). Not sure what I should make of that lol...

@roberta
Guilty as charged lol, sorry! If I ever get round to uploading my real-life Finds, half of them will likely be 'from a random market stall in Singapore'

@DonnaF
I didn't even think of the family dynamic there - it feels almost like a rite of passage for most daughters to hate whatever their mother's personal style is (not really hatred but just not wishing to emulate it - like @helena said, to develop their own style instead).

Gosh I never thought that youngsters would not like a compliment. Maybe because I don't have kids. That said I only compliment my close friend and SIL.

I have complimented strangers on their outfits and have received some which I found nice.
Funny story - I got a pair of new glasses and have received many compliments on them, however an 81 year old aunt announced on several occasions she hates them on me and I look terrible wearing them. She has decidedly never been in to style and fashion and yet I find myself not reaching for this pair now after her comments lol!
One negative comment and that's the one I listen to ! What's wrong with me ??

I just told Little Mr. A about this conversation and he said something I found quite wise. "It's not about age. Anna Wintour is 73 and I'd take a compliment from her any day."

I compliment others without thinking about their age.

April, that is a wise comment… but it sounds like the wisdom of age to me

My feeling is that only the young could turn a complement into a criticism!When they get to my age they will be overjoyed if they get a genuine complement .Aren’t some of the top fashion designers in the mature bracket?l bet this young person also writes lists about what people over30/40/50 shouldn’t wear as well.