She's 33, smart and accomplished, and dressed like that for dinner with your boss. I think one of you is confused. Or else that description doesn't mean what it used to mean.

Maybe you could surprise her with the little black dress and a hello kitty thong or something. But at 33, she probably figures she knows how to dress herself. (She's wrong, but that's beside the point.)

Anyway, good luck.

Oh, maybe she's playing you! Maybe she wants to see how long it will take you to say something. Or, maybe she's trying to end it and wants you to start things off. Just sayin'.

Why does it have to be a production number of sitting her down and having a really heavy conversation about her wardrobe?

Why can't he just say, "Hey, could you wear your [insert preferred sophisticated dress here]?" Or "Wear something sophisticated when we meet my boss for lunch."

She's 33, single, smart and accomplished. So, presumably, she has a job and works in a place where dressing like an adult, if only business casual, is expected. So she probably has the clothes and knows how to wear them, and also knows that certain attire is appropriate for certain occasions. So she's saying something by dressing in Hello Kitty to meet your boss. And that something isn't very good. You need to have a serious talk with her and seriously think about this relationship.

I would talk to her about it and then drop it - if you don´t like it drop her as she is aware of what she is doing.

DrMaturin lots of us work in industries where you can wear daisy dukes and flipflops - and the boss does too. Software, internet, creative fields etc. Business dressing has gone out the window. So if they are from say him banking and her software they need to have this talk, she may be equally self-conscious at his suits when meeting her co-workers.

I remember hearing on a TV fashion program (probably "What not to wear") that "dressing young" makes you look older by comparison. It's true.

But obviously the LW's girlfriend hasn't gotten that message. And zapf is right -- I know tons of successful people who work for gaming companies, animation studios and other creative/tech-y careers, where brightly-dyed hair and cartoonish get-ups are encouraged.

I agree with Amy that the LW should be able to ask her to dress a certain way for occasions involving his work and his family.

"Hey, so for dinner with my boss tonight ... can you wear that nice, fitted navy-blue dress you have? And the grey sweater? You know how stodgy my coworkers are."

Or "So, for my cousin's wedding ... You know how WASP-y my family is. Could you wear that little black dress with your pearls? For me? Please? It would mean a lot to me."

You lost me at "She's 33..." and wearing Hello Kitty shirts and pig tails, LW.
No. Just... no...

Its one thing to appreciate the child-like innocence and girlyness if it, and maybe have a passable ADULT looking piece of kitchy jewelery that can be a cool conversation piece. It's another thing to dress like a fan girl. Save that shit for the convention and dress like a goddam adult. ESPECIALLY when meeting the boss. I mean, how would one NOT know that at 33?

I have a hard time accepting "naivety" as an excuse for dressing inappropriately for an event. Especially at 33. That's definitely old enough to have lived in the real world long enough to know what's appropriate and what isn't.

I take issue with folks who deliberately dress in an inappropriate fashion to events and then get offended when they are called on it. Those people, are rude. Period. "They'll take me for me or not at all!" said the "gentleman" who wore tattered jeans and a tee shirt to my friends recent formal wedding. He almost wasn't allowed in the reception hall but one of the men there had a spare blazer in his car and loaned it to him. The venue still didn't want to let him inbut the groom worked something out with the venue and he was allowed in. The process took only about ten minutes but it did cause quite a ruckus. The couple tried to be gracious about it but I could tell they were bothered by it. Unfortunately, I ended up at the table with him. He spent the whole half hour before dinner bitching about how he shouldn't have to dress up... that they bride and groom should want him there because he's their friend and not because he's in a suit. After my and my table-mates attempts at changing the subject or ignoring it, I finally had to say something to him. I told him that if he really cared about the bride and groom, as a friend, he'd have the decency to honor their wishes for THEIR wedding. I also said, "It's a formal wedding. It may not be your style but sometimes, you have to cater to other peoples tastes for a few hours."

He said, "Well, they let me in so what does that tell you?"

I said, "Shame on you. Do you understand the position you just put the groom in? Of course he let you in. He's a nice guy and far too polite to tell you to your face that you're an ass. But I'm not. You're an ass. It won't kill you to put on a damn tie, you slob." He continued to make passive-aggresive comments all night, but under his breathe. He also bitched about the food, the deocrations and the DJ. I wanted to stab him with my fork by the cake cutting.

I did try to apologize to the bride later for my outburst. She actually apologized to me. I found out later that the couple never wanted to invite him but he's a distant relative of the groom and his mom sorta forced the issue so he was. This, from what I gather, is par for the course for this guy.
Disgusting.

Positive reinforcement.

There are clothes my husband loves, and he lets me know it. So I wear them.

In whatever outfit you like, tell her she's super hot and touch her repeatedly like she is so amazing you can't resist her.

If she is wearing something you hate say in a disappointed voice, "Oh, I was hoping you would wear X, I love that outfit".

@zapf.

I understand different occupations have different dress standards. I can often just wear scrubs, basically modified pajamas. But I still bet that in order to get her casual attire wearing job the GF had to dress up for the interview. She knows better, she just decided to embarrass her boyfriend for whatever reason.

I said, "Shame on you. Do you understand the position you just put the groom in? Of course he let you in. He's a nice guy and far too polite to tell you to your face that you're an ass. But I'm not. You're an ass. It won't kill you to put on a damn tie, you slob."

I love you. Will you marry me?

Yeah, this might be a lifestyle difference thing. If she's into the punky alternascene, and he's more mainstream, they may not be compatible.

My senior year of college I realized I couldn't have green/purple/pink/blue hair anymore and dyed it a normal color again. Various steps of my life have seen me shed various clothing choices... most recently, a couple years ago I realized rhinestone hair accessories aren't the best for everyday wear.

But I'm not committed to an alternative lifestyle or scene.

MonicaP, fuck yes. Together, armed with Amy's book, our sense of style and some snark, we can wander the country beating bad manners and bad style out of everyone!

MonicaP and Sabrina: can we make it a threesome?!

it's my understanding that adults who can't NOT dress as children is considered a pathology of some kind. maybe even just a fetish or addiction, but one of the psych classes i took in college identified this as an actual, real disorder that some people suffer from. no clue if that's true or not, but it's the first thing that came to mind when i read this. anyone know? if it's a possibility, LW should be aware.

Lori... why the fuck not.

Let's conquer the world, ladies!

I teach English as a Second Language at a community college in New York. One of my former students is a statuesque, strikingly beautiful Asian woman who dresses like a little girl (pigtails and Dora the Explorer t-shirts) and always brought a Beanie Baby to class. She spoke normally when conversing with other women but turned on a "widdle girl voice" with men. Really odd. And she did it ONLY in English--her Chinese speech patterns were "normal."

MonicaP, fuck yes. Together, armed with Amy's book, our sense of style and some snark, we can wander the country beating bad manners and bad style out of everyone!

It would be a Snarknado!

My workplace is casual, but some people take it too far. One woman, age 45, consistently comes in wearing flip-flops, short skirts, and superhero t-shirts. She's a great person and a great manager, but I wonder if upper management takes her seriously. (She also has trouble getting dates, but that's another subject.)

It depends a lot. I have worked where we had casual Fridays -- that meant we could wear cotton suits (as opposed to the usually expected wool). Where I work now is quite casual. Hello Kitty would be fine were I work and would be completely appropriate for most meetings with my boss. We are a results orientated business instead of an appearance based on. My manager has said he wore a sweater and jeans to the interview for his current job.

Without knowing more, her general attire sounds fine and generally acceptable...perhaps not what you would want to wear.

Ok, this same company had a celebration dinner and they gave some weird name for the dress code...that when I looked up was an old term from Europe where you started sporty like for Polo but then in the evening you changed into a tux with tails. A week before some clarification came out but it was not much better. The rumor was a suit and tie was fine. At the actual event one high up manager was in a tux while another was in a casual button down with jeans.

Gee, I dunno why there's a problem. Abby hid the tats and the Goth stuff for him.

I continue to be fascinated by how people go crazy about clothing. For instance, at church.