remix 20.10.08 by et sans, on Flickr

My criteria: It has to be slightly nicer than what I would wear to a non-casual office, but also not too businessy [...]]]>

remix 20.10.08 by et sans, on Flickr

My criteria:
It has to be slightly nicer than what I would wear to a non-casual office, but also not too businessy or bridesmaidy looking. I don’t want black or white or a really bright color. But it should be a color that will match a pair of shoes I already own, so I don’t have to buy new shoes. It needs to fit me well and flatter me, but it can’t be too revealing (trampy) or unrevealing (dowdy). It should look classy and modern, but still have somewhat traditional lines because I just don’t get all the crazy fashion forward stuff Carrie wears on ‘Sex and the City.’

Really, is all this too much to ask?

Also — and I’m going to date myself here — I’m having a hard time switching to bare legs under a dress after decades of wearing pantyhose. I know that pantyhose has been “out” for a long time now, and I’ve sort of sidestepped the whole issue for the last few years by simply not wearing skirts. I generally prefer pants to skirts, anyway, but I haven’t quite made the leap to wearing some kind of elegant pantsuit to a wedding. Some women do it, and they look great, but I just don’t feel like I’m an elegant pantsuit kind of person. Plus, the wedding is in Vermont in October, so it seems like bare legs under a dress would just be downright cold.

So now I’m thinking maybe boots would be a good solution to avoid the bare legs issue, but then not all dresses are going to look good with knee-high boots. Aaaaaand now I have to back to the second paragraph to add more items to my perfect dress criteria.

I think I’m going to blame ‘Project Runway’ for this exhausting search for the perfect outfit. I keep imagining what Tim Gunn would say as I try on dress after dress. So far, he hasn’t said much that’s nice.

I probably tried on about 20 dresses tonight. I bought the two best ones to bring them home and think them over, but I’m not convinced that I’m keeping either of them.

My inner Tim is not yet happy, but I’ve still got three weeks to figure it out. Three. exhausting. weeks.

Any advice?