I don't see pretty as conveying any "weakness" or being associated with youth but I guess some do.
Lyn, Your thoughts on the subject are interesting as you are in the medical field. Something people think of as cold and sterile.....although that may not be the case with therapy... I'm not sure. Your style is very friendly and light. I imagine it works for your purposes most of the time quite nicely. You can always deflect assumptions with your brain.
Or sometimes I let them stand.

"Oh... I forgot money to buy coffee. DOES ANYONE HAVE MONEY TO BUY COFFEE?"
I find "pretty" is a guy term. My husband's highest accolade! I think pretty has a feminine connotation but not necessarily youthful as other have said.
I had a thought: There is another category, drop dead gorgeous. It's different from pretty or beautiful or gorgeous. I can't say what it is in a woman, but I have seen it in a man. There was a guy we called No Socks. He was so drop dead, people would see him and then leave the room laughing.

You know, coming to have a look-see and then laughing is exactly what attractive isn't. Isn't that weird?
I haven't had time to read all the comments but I will go back. Just wanted to confirm that I do think "pretty" can be taken seriously. And I do see being called pretty as a compliment:) I think like most things "pretty" has many modes. We are bombarded by media advertisements of 'pretty' young things wearing skimpy outfits promoting soft drinks for example but that is not the kind of pretty I was thinking of when I made the comment on DV's post. When I think about it, it was the femininity of the look that led me to 'pretty". I fear I may have an unconscious association of pretty with the very young, how often do we find ourselves referring to a little girl as pretty?
I agree Rachy -- I saw a young man in the sandwich shop today I could barely place my order because he was so distractingly gorgeous. Drop dead gorgeous male or female tends to turn most people into yes people.

Are you kidding me Rachy? I know exactly what you mean. I had one of those no socks moments at my dentist office years ago. I swear, had I been single at the time, I would have made a move. That is also how I would feel if I ever meet Keanu Reeves in person, one day. I am waiting for Una to hook me up.You are a hoot.

Very intrigued by Rachylou's distinction between pleasant and non-disturbing pretty and pleasant and disturbing beautiful. Neither precludes being taken seriously nor assures it.
I think Rachylou's right that there's a distinction between pretty and beautiful (though perhaps they can overlap to a degree...Venn diagram, anyone?? ....where does "drop dead" go?) I also think Shevia's right that neither precludes being taken seriously. But either might make it more difficult.

I take "pretty" as a compliment, too.

It's partly about taking care, isn't it. We "pretty ourselves." If someone says we are pretty they are noticing that we have attended to the details.

This is another one of those amazing discussions. Growing up in the 50s, there were girls who were pretty and girls who were intelligent and it seemed impossible to be both. I would probably take bring called pretty an insult then. There is still some of this thinking around, but I hope that females can be recognized as both today.
Didn't President Obama recently get criticized for calling a woman pretty or attractive (even though she is)? We were in Japan and I didn't get the details.

Joy, I think (or at least, I hope) things have changed. When I was in high school in the 80s, you got bonus points for being both pretty and intelligent. Extra bonus points if you also had personality.

Haha, Suz, Venn diagram. I'd forgotten about those. Don't we need three terms to draw one? Pretty, beautiful, attractive, maybe?
A very interesting conversation.

I've always thought both pretty and cute were compliments, neither referring to youth or weakness.
I will ponder today at lunch whether there is overlap between pretty and beautiful (and I will, sicher, because that is sooo me). In one way I'm inclined to say no, but in another - I feel they have a similar attractive effect.

I will also ponder where drop dead goes, because I don't think it has the same attractive nature. It has a brain paralysing, eye-burning effect. It's a thrill, like an electric shock, and not necessarily enjoyable in the same way. I mean, for real, people did not like to be near No Socks. There would be people going in and out of the kitchen for little rest breaks.

The pretty or intelligent question... an interesting one. The sort of thing one contemplates in middle school, and it's pretty critical one in determining your path to success. No one asks beautiful or intelligent, tho. That's probably telling. Anyways, I think all "high potential" middle schoolers know it's better to be pretty. Pretty gets you perks and you don't have to do anything. Intelligence, tho, och! The suffering! Everybody is so freeking slow!
Pretty, to me, is completely unrelated to being taken seriously. Pretty, beautiful, cute, etc. are overlapping terms in my personal dictionary. A person can be one, more than one, or potentially all of them. I do use "cute" sometimes when referring to adult women, but I am usually thinking of what they are wearing as a component of how they look to me. As in "you look really cute" is another way to say "that's a cute outfit, and you look good in it".

I remember hearing one of my best friends refer to several young girls dressed for their Quinceanera as "lovely", and I thought that was the best descriptor she could have chosen. It seemed to imply something more than "pretty", but I find it difficult to describe what it is. It's as though "pretty" is on the surface, but "lovely" implies a glow from within. BTW, she is a linguist. She puts effort into finding the perfect word for the occasion.

I've been known to use the word "handsome" when referring to a woman, which does not mean I think she looks like a man. I believe this word pops into my head when I see a beautiful woman who has a strong, distinctive bone structure, if that makes any sense. Surface beauty, or prettiness, or cuteness may change or fade over time. A handsome woman will be handsome no matter how old she is, because the architecture will still be there.

And finally, I remember a pretty funny bit about all these terms from an episode of News Radio. I can't look for it now, but I'll post it if and when I find it.
Dstalksalot, do you have a friend with experience interviewing people who could do some mock interviews with you? It's sometimes hard to tell what we are doing right or wrong when we are trapped inside our own heads. A frank critique from a professionally minded friend could give you insight into how you are presenting yourself in a way that you just can't get on your own.

If you don't have someone like that in your life, maybe try this. If you feel that an interviewer likes you personally, but you still don't get the job, try getting in touch with him or her later and ask for honest feedback. The worst they could do is say no.
I think I'm getting lost in translation here.

I always understood 'pretty' as in 'fine looking' or 'rather attractive yet not truly beautiful'. Also a feminine adjective, like you wouldn't call a man/boy 'pretty'. I never thought it would sound juvenile though!

Pleas enlighten me here?
I have also never thought of "pretty" as meaning juvenile, and from my observations of a few decades of work, being pretty (applies to others, not me) did not keep women from being taken seriously; they had the necessary skills, ability to present themselves, and good office politics. But of course a lot of pretty women didn't advance either.

Cute is an adjective I use for children but as others have said, I'd use it for an adult in referring to her outfit or total look.

To me, feminine is not the same as girlish or twee, but it seems to me on the forum that frequently a feminine look is not held in high regard and considered girlish. Guess my rule is that pink ruffles would be twee, but neutral or dark ruffles are adult.
Perhaps pretty is associated with young people because there's a sense that beauty requires the depth borne of maturity and experience.
I think of Roy Orbison growling and it works for me.
http://www.youtube.com/watch?v=CPWwGFSBZn0

Re: drop dead--it's very rare I've encountered that but yes, it's entirely disconcerting and not really pleasant when it happens.

I think of pretty as an asset to professional success. Quite easy to be taken seriously if you wield it well. The head of our agency is gorgeous (and pretty and beautiful--they're not the same but she is all of the above, the sweet spot on the Venn diagram) and also the sound of her voice is beautiful. We all take her seriously.

Growing up in the sixties and seventies I definitely believed in the smart vs pretty dichotomy. I also believed that true beauty knew no artifice, and that any other kind was not worth having, so it took me forever to learn to wear makeup, style my hair, etc.

Dstalksalot, you are welcome. And good luck with the job search!
I am laughing at the link T-Rex posted! It's funny because it's so close to the truth!
I have to say, DV, that I would be flattered to be called pretty. And sometimes I think I would give up any claims to being taken seriously, if that's what it would take to be unquestionably pretty. But I know I wouldn't really be happy if people didn't take me seriously; in fact, I couldn't bear that.
Yes, if I could have only one or the other, I would choose being taken seriously. Being pretty is a very good thing, but not being taken seriously would make me have screaming fits.