Questioning My Fashion

First let me preface this post by saying that I generally feel very confident in my fashion choices.  I kind of pride myself on being appropriately dressed for whatever the occasion dictates.  I know that I don't have the best or the most expensive or the trendiest clothes, but I think I generally look good and fashionable.

I recently attended two different events to which I wore the same dress.  A photo taken at the second event shows the dress I wore - a black and white cotton print, fit and flare, knee-length dress by Ralph Lauren.  It has a self-tie belt and fun pockets.  Though the picture below isn't the best, it's a really flattering dress and I've gotten a ton of compliments on it.  When I found it, I had no event to wear it to, but I absolutely loved it, so I bought it anyway.

The first event I wore this to was an anniversary party for my cousin's boyfriend's company.  (Whoa, that was long winded!)  I wore it with very simple kitten heel sandals.  I was dressed completely WRONG!  The girls who were there were some of the trendiest dressed girls I have seen in a long time.  Super trendy clothes, purses, and shoes.  Every part of my outfit was too subtle, not trendy enough, BORING!!!  Even the guys there were seriously Euro-trendy, wearing skinny jeans, deep v-neck tees, and pointy shoes.

The second event I wore this to was a Design Council party on the rooftop of the Art Museum residences.  This time I dressed up my shoes just a bit to simple black pumps from Coach.  Not trendy by any means, but beautiful and timeless.  At this event, I felt appropriately dressed.  As you can see from the photo, some people were similarly attired, though some were fancier.  Some were dressed much more casually, too.  This time my shoes were the thing that stuck out.  They were much too simple.  Most of the other women had trendy wedges, platforms, booties, or funky sandals.  It made me want to update my shoe wardrobe - IMMEDIATELY!

Though I can't (and don't really want to) do anything about the trendy clothing, I can do something about the shoes!  I went to DSW this weekend on a quest for new, trendy shoes.  I didn't do too well.  :)  I only got one pair of totally trendy shoes.  They are fabulous peep toe booties with hella high heels and a front platform.  They're black leather with trapunto stitching.  So much fun!!!  But the other three pairs I got are much more refined and classic.  They are all peep toes, though, so I guess I had a theme going.

 Maybe I'm too old to have too much trendy stuff in my wardrobe?