Would you tell someone that he/she looked fat, dirty, or ugly?
Our filters tell us that, even if we’re looking at someone and we’re thinking “Wow, she needs to lose weight or “Oh my gosh, he needs to take a shower,” we don’t say it out loud.

Our filters should be set that way for opposite situations. Some compliments might be too personal. “You’re beautiful” or “You look pretty, today” or “Your make up looks good, today” are, most of the time, not necessary, Just as telling someone that he/she is overweight or that she/he isn’t dressed nice isn’t necessary.

What we look like doesn’t usually matter in a professional setting. There are situations where we can say something just to help a colleague out; for example, it could be that a colleague has mascara on her cheek (or his) or his/her shirt tag is hanging out. It could be that a co-worker is getting ready for a presentation and he/she looks great! If he/she asks you, “How do I look?” this would also be when this kind of comment would be warranted.
As a boss or a supervisor you may have to, at some point, explain to someone your company’s professional attire preferences, instead of saying, “you’re dressing wrong,” you can give that person or give the whole team guidelines for what they should wear to ensure everyone is “on the same page” and comfortable in this work environment.
I have talked to clients who felt awkward about talking to co-workers about how they were dressed, so even when it’s appropriate to say something, many times these conversations are not had…because they are awkward.

I recently met a gentleman at a professional event who I thought was very attractive. I got a flashback of moments when men said something to me that was unwarranted. I knew if I didn’t say anything to this man about his physical appearance that he wouldn’t know how I felt and the interaction would remain professional, so I didn’t say anything…it worked…it’s that simple.
I’m saying all of this because I have been in situations when I knew that I looked good. I got up in the morning, and I did everything I could to look really nice, but I didn’t do it get that compliment; I just did it because I wanted to look nice. When a client of mine told me I looked nice, it was awkward for me. He didn’t think anything of it, but I didn’t need that compliment. It wasn’t necessary or “missing.” If you say it out loud it changes the context of the meeting from professional to personal.

If you are on a date…compliment the person you are taking out. If you are meeting someone for professional reasons, keep the conversation professional. Any comments about the other person personally makes the conversation personal.
Once you have a working relationship with a person it may become more appropriate to compliment that person, but only in circumstances when it’s warranted. I have clients whom I have worked with for years, but the situation is still professional, so I still really don’t need that compliment.

Our filters tell us it’s OK to tell someone they look pretty or beautiful, but this might have an impact on our Know Like Trust score. Telling someone she/he looks beautiful or handsome or giving somebody a physical compliment when it’s not completely necessary, could be creating issues you may not be considering. In the context of the situation or the conversation, if it’s not necessary, leave it out. Don’t say it. The lack of the compliment won’t have a negative impact on the interaction. The inclusion of the compliment might.