Dress for success

For a very long time now I’ve said that if I had the money my wardrobe would consist mostly of clothing from Ann Taylor. I guess it’s always had that look of sophistication that I fancied I’d have one day. That day is unfortunately not today but that hasn’t stopped me from very, very slowly trying to build a wardrobe that looks more like that of a 30-something and less that of a teenager. I don’t plan on ever becoming mature in the sense of giving up all my dorky interests and endeavors, I’d just like to be able to look like a grown up should the need arise. As I’ve said before Italians just know how to dress themselves. They take fashion risks but it doesn’t look crazy, it somehow just works. I envy their ability to put together outfits that if I were to wear them would look ridiculous and yet they pull it off. My gut feeling is that says more about me and my lack of self-confidence when it comes to dressing myself than it does about their innate ability to pick incredible clothes.

My cousin Bobert (aka Bobby, aka Robert) is marrying a most lovely girl, Amy, in September and I am at a loss as to what to wear. I would like to buy a new dress, to go outside of my comfort zone a little bit and try something I wouldn’t normally try while using as an excuse the fact that I live in Italy. By claiming that I’ve been influenced by European fashion I’m hoping that I’ll get over worrying about what the US trends are and just enjoy clothes for what they are – an expression of one’s personality. You gotta fake it til you make it, right?

I’ve been browsing numerous websites looking for inspiration and ideas and came across this dress yesterday:

I like the classic look of it. I can imagine Audrey Hepburn wearing something similar but I worry it’s too safe, too much like all the other stuff I’m already drawn to. Wouldn’t it be better to do something a little crazier? I don’t know. This is where I get stuck. I over think it and then can’t make up my mind. With a dress like this I could get some bright red shoes or maybe some yellow ones, and give it a little pop. But then I think maybe I should do something totally different, something more like this:

Or this:

Both of these are a little out of my price range, and the second one may be a little short for my liking but you see where I’m going with this, right? I plan on going shopping up the hill at some point in order to see what kind of things I can find here. The price point will probably be not so great but it will hopefully give me a better idea of what looks good on me.

Do any of you have any favorite websites or stores where you’ve had luck finding awesome but not incredibly expensive dresses?