This coming week I have two special work occasions coming up, and I'm plotting out what to wear. As you know, I am a teleworker and only hit the office about twice a month.

Being in high-tech, our dress code is pretty casual. Actually, VERY casual. Most people schlump around in jeans or khakis and look, well, like they just rolled out of bed.

Smart casual has worked very well for me - jeans but taking it up a notch.

However, these two work occasions are a bit different:

1) Good news! My informational interview on friday has led to an invitation to meet the hiring manager (a major heavy hitter in our company) at a swank hotel downtown for breakfast, to "continue our conversation." She just happens to be in town next week for a conference.

Now, the deal is, those who work in our HQ on the West Coast dress totally differently than those who work in our East Coast offices!!! Despite a "business casual" dress code, people dress very smartly - you do still see jeans but it is also not uncommon at all to see suits and ties. Before YLF, even in my best-dressed work clothes, I'd feel slightly frumpy in comparison when I traveled out there.

Likely this manager will be in a suit - since she will be presenting later at the conference.

This is technically not an "official" interview. The situation is such that it actually looks like the job WON'T be a good fit for me afterall: they need someone immediately, and someone on the west coast, or willing to basically live out there for weeks or months on end initially. I just can't do that at this time in my life.

BUT..... the hiring manager invited me to breakfast anyway, because she anticipates hiring a lot of people over the year.... and was intrigued by my background....

So if not *this* particular job, perhaps one down the road when the timing is better for me too. (I told her that although my bosses are well aware I am ready to move in a different direction, I had committed to execute through end of year - if not a full 9 months more - and I did want to keep that commitment, but knew I'd kick myself forever if I didn't at least talk to her about the job opening).

Sooooo.... what on earth to wear???? I don't even know if I have any dress slacks that fit me anymore, to mix and match, and make a suit. And, it's not an official interview anyway.

Can I get away with the dark skinnies, a jacket, and a blouse? I'm thinking I might be able to get away with that.... but I'm on the fence. For this department, how you look (from the waist up at least) is highly, highly important. Looking completely stylish and trendy - with attention to detail from the waist up (jewelry, layering, etc) - would be a huge, huge plus in my favor for this job. A regulation interview suit would be completely wrong, I am thinking.

Hmmm.... I need to strike a note of "business appropriate, 20 year veteran, but young and hip and with it enough to get a younger market, and with great taste and style. Someone you could trust whether you put her in front of a business or a creative agency. And---- someone who would look great on camera."

(Now you know that last bit, for me, is one of my intimidation areas - but YLF has been wonderful in helping me get over that fear of cameras.... )

2) Second challenge: We have a major company event going on. Big-wigs flying in. Will be a mob scene. I will just be one employee in a big crowd. I think smart casual formula with jeans will be fine - provided I go with jacket not sweater - just in case *somehow* I get to meet one of the big-wigs.

ALSO - later on after this event - I'm meeting Nicole for the first time!! WOO-HOO!!! Looking forward to that - way more than the work event.

The question here is: are the skinnies okay to wear to my office? I don't know why, but I seem to have this mental barrier wearing them to the office. Maybe because they are so form-fitting?

Truth is, I feel like a little sexy minx in my skinnies... which gives me pause when I consider wearing them to the office!!! Although bizarrely, I *could* see me wearing them to the breakfast interview... hmmm... why is that?

Would bootcuts or my dark wash flares (which are more like denim dress slacks) be better? Or is this just all in my head and I need to get over it?

Please advise! I'm hoping to slip out to the mall today or tomorrow, but on the pants front, it's unlikely I will be able to find anything in time (considering need to hem).