Question for the Ladies

Ladies, do you ever have a hard time dressing up?  I do!  Sometimes I put on a really cute outfit and I'll feel I'm too dressed up! I put on a really cute dress a few days ago.  I knew it looked cute but, I got a little bit anxious that it was too cute....and that my boobs were popping out...and that maybe the hem might get dirty....and maybe I'd be overdressed in the city.  So I changed!  Into a denim skirt and layered tank tops!  Why?!  I had the opportunity to look totally cute in Athens!

I feel like I do this all the time - which has left me with a somewhat uniform-ish wardrobe.  Denim - pants, shorts, skirts - with cute tops...mostly tank tops.  The only thing I don't mess around with are my earrings....I always go sassy.

The only time my low key style really works for me is at the beach - I can truly put together shabby chic outfits that are beach fabulous.  What's the secret?  Again - EARRINGS!  If you're lounging in a bikini make sure you have on sassy earrings - then people will look at your earrings and not your love handles :)

What are your thoughts on dressing up or dressing down?  Any tips on how to leave the house in a fashion forward outfit - with confidence?!