When is it appropriate?

As a mid-50s dude I avoid complimenting young women if they look nice because it would seem kind of creepy.

I was in a store the other day and saw a woman (guessing in her late 60s) with long white hair and a pretty face that left me breathless.

I was very tempted to remark about how good she looked, but held off. If I was single I would have gone for it, but I wasn't trying to pick her up.

Should I have said something?

Something like, "I just wanted to say that you're extremely beautiful" is nice.
 
Interesting question because it mostly involves confidence, specificity and no expectation. You can compliment both genders with this method. Focus on something in particular and make sure it isn't sexualized.

"I really like your jewelry."

"I love that hairstyle on you."

"Your T-shirt makes me smile."

You can compliment most people by reading their body language, whether they're open to a comment or not. Some people aren't, if their body language is closed, if they're obviously avoiding eye contact, leave 'em be.

Rather than telling someone that they generally look hot or lovely or anything that might be construed as a wedge to a come-on, just pick something specific and be kind.

They might think you're gay and since it's just a compliment to a stranger, that's the tone you might want to set anyway.

Making someone else smile shouldn't be about you.
 
Liking something like a t-shirt is better than just admiring a person for their ability to choose good genes.
 
Liking something like a t-shirt is better than just admiring a person for their ability to choose good genes.

Yeah, that's my experience. Same as I try not to put someone down for something that was not their choice, I try not to compliment someone on something that wasn't their choice as well. Less about bodies, more about style.
 
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