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I've always been told the best thing to do is stick to complimenting things that are their choices.
Not great: That outfit makes you look good!
It's you coming off as being interested in their physical appearance, not the outfit.
Better: That's an awesome T-shirt! Where did you find that?
It's you thinking they picked out something cool or stylish and you like their taste in outfits. You're putting the attention on something they did, not anything about them appearance-wise.
Especially if they don't know you, odds are they have no desire to hear a stranger's opinion on their looks. That's too personal. But a stranger agreeing with their decision on something like buying something cool generally isn't.
Of course, some people are more or less open to any conversation with someone they don't know, so if you still get ignored or get looked at like a creep, you don't know their background and you respect that and don't persist.
A good rule to go by is if you're a guy, think of a guy coming up to you and saying the same thing or you saying what you're going to say to another guy. If you wouldn't tell another bro that he looks good wearing that, maybe don't do that to a girl. If you see a guy wearing a band shirt of a group you like though, you'd probably be ok saying "whoa, I love that band too!" or you'd be cool with some random dude telling you the same.
You shouldn't be afraid to talk to people, but you should always be respectful and keep in mind how well you know them and keep conversation at that level of appropriateness.
In addition to this, I've heard people say to do 'drive by compliments'. If you're not trying to start up a conversation or don't want the person to worry about a conversation, you can drop the compliment right as you're about to leave the situation. It has its downsides as well
This has been my strategy. I like to compliment people because I can remember the few times it's happened to me, but I'm not trying to creep anyone out. Mostly stuff like "awesome shirt!" or "hey, sweet hat". Never "nice cock, bro". And never with the intention of starting a conversation. Mostly like passing by someone and pointing "excuse me, love the boots.", then keep on truckin' by.
Heh i have a couple stories.
At costco picking up hotdogs for the crew, get back to car and notice older (60+) lady with Doc Martins on (i figure shes an old hippie but doesnt really matter) so i tell her i love your big stompy boots! And because of her style i add, "you may not but i think you would love Jon Fluevog shoes" she thanks me and says she has a couple pairs and loves them but doesnt wear them every day so they last longer.
Pleasant 45 second interaction.
At a music festival in victoria bc watching a metal band called Malahat, see a younger woman wearing the same colour converse shoes im wearing standing next to me, bamd pauses and i tell her she has terrible taste is shoes as im looking down and pointing to my own shoes. She was confused for a moment then laughed loudly enough security looked my way.
Have used the shoe bit a couple times stuck in close quarters (elevators hallways transit etc) a few times not always successfully but usually it goes over well when they notice im wearing the same shoes.
Sometimes i have to explain it was just an intentionally bad joke(i do love a bad pun and a good dad joke) but rarely usually is well received. But thats literally all i intend and it usually happens in passing.
(Middleaged white guy beardo)
I wish someone would drive-by compliment me with "nice cock bro"
Sorry to look twice, but wow, nice cock, bro.
Leaving a bar to catch a train and I did this when closing my tab. Ended up in a conversation and missing my train.
Yes I like this! When people (even random strangers) compliment an external thing and it reflects something like a mutual interest that can be pretty cool. Especially if it’s a fellow metalhead.
I approve this message.