Zap and Angie, I totally agree. I am still confused on pants vs. skirt suit and that is a problem too. If I wear pants i'm just going to wear booties but it's the skirt that's a problem. There's no time to get a suit tailored and whatnot, so I'm stuck with my closet.

Just to add, the person who is interviewing me is not a stranger but a friend and social acquaintance, because that's how this town is. So it's someone who KNOWS me, not a first impression.

Goodness, who knew this would be so difficult for me? Just looking at pumps and Mary Janes made me feel odd.

Thank you all for putting up with me!
Una, I probably have more conservative (office-dress wise) opinions about what is appropriate in the legal world. I know what I see every day among my colleagues though and that shapes my opinions. Male colleagues are not generally all that particular, bit senior female colleagues who fought their way tooth and nail for recognition and respect tend to be very very conservative.

I think that part of what makes this suit/shoe choice very challenging is that, like banking, investment, and educational administration, law is an inherently conservative (dress wise!) field. If you are going to wear a suit with a skirt, I think you really need a more refined shoe. I can see a heeled loafer, but it would need to have a feminine shape and lower front in order to look professional with a suit and skirt. It is going to be very hard to find a funky shoe that is going to work with a dress and jacket or skirt and jacket suit combo and look appropriately professional.

Can I be totally over-reaching and ask this: If you had to have one dressy, more conservative shoe in your closet that will serve as your fast fallback when you have to dress up for a more conservative environment, what would it be?

I don't think it makes sense to focus on something that you'll immediately be able to seamlessly integrate into your daily wardrobe rotation for this particular shoe.

My FFBS is a pair of stacked but feminine heeled almond-toed black pumps that I bought at Nordstrom many years back. The almond toe lets me wear it when toe trends are more rounded and when they are more pointed. I also have a secondary FFBS that is my pointy-toed, high-heeled classic pump in black suede from my WIW earlier this week. My almond-toe shoe is probably seven years old. My pointy-toe one is a few years old, but is such a staple, always replaced, that I can't be sure. I think you need to focus on a shoe like that. I think, in part, that is why I loved the shape of the corso como so much.The height not so much, but the shape for sure. Everyone has to have certain basic items in their closet that they don't reach for as their cutting edge item, but that serve as a foundation. This shoe should be one of those. It is like your suit. You are trying to find one now because you need it. You may not need it again for years. However, when you invest the money in that one classic item, you can reach for it four years from now and it is going to work well for you. A trendier item isn't going to do that for you.
I honestly don't know what is appropiate then Una. I don't consider whether the person knows me. As a matter of fact every time I go for a promotion, I need to take an exam and an interview. I end up being evaluated by colleagues. I really don't go by whether or not they know me, I dress for the occasion, but heck, you live in Alaska. I have no clue. Go with your instinct. I guess at some point in time it could be a good idea for you to get a couple more corporate, business like, conservative pieces, so you don't run into a situation like this. you are bound to encounter this in the future, especially in your field. For now, I agree. Too much of a time pinch. I thought you had found a pant suit for whatever reason. Go with whatever looks more confortable.
kcs, you are totally right. My entire environment is SO casual that I have almost no perspective on business wear. Only trial attorneys in trial, wear suits, and even then not always, as a jury here tends to frown on too much frippery. It is a whole different world.

That said, I am trying to balance between finding the right shoe and looking confident, which I fear will not happen if I can't walk comfortably. Right now I'm leaning toward black dress pants, Theory jacket, silk tank, and a pair of sleek boots or booties from my closet - just have to figure out which ones are best.

Thank you so much for the reality check!
Zap, I really appreciate your perspective, as I know you also work in a conservative environment. If only I had more TIME! I'm usually the person who regrets buying for events that may not happen - now here it is and I don't have what I need!
Yeah, I think pants suit + booties is probably the best idea. Being comfortable is important! I have something of a similar issue, although I hardly ever have call to wear a real suit and don't even own one. But anytime I need to dress businessy I tend to default to trousers because of the shoe issue. Basically, I have never, ever found a pair of closed toe pumps that are comfortable, and trousers allow me to wear boots or oxfords underneath so at least I'm not limping by the end of the day.
I know Alaska & your particular work is less conservative and you may not have time now, but for the future, have you seen http://corporette.com? They are talking about shoes at the moment.